| Revision as of 10:06, 9 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 08:41, 13 November 2023 edit undoJohn of Reading (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers768,720 editsm →top: Typo fixing, replaced: was name → was namedTag: AWB |
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{{chembox |
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{{chembox |
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| verifiedrevid = 409355770 |
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| Watchedfields = changed |
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| ImageFile = SEGPHOS.png |
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| verifiedrevid = 428222586 |
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| ImageFile = R-SEGPHOS.svg |
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| ImageFile1 = |
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| ImageAlt = Skeletal formula of SEGPHOS |
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| ImageFile1 = SEGPHOS-3D-spacefill.png |
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| IUPACName = 4,4'-Bi-1,3-benzodioxole-5,5'-diylbis(diphenylphosphane) |
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| ImageAlt1 = Space-filling model of the SEGPHOS molecule |
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| OtherNames = SEGPHOS<br>5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole |
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| PIN = (2''H'',2′''H''--5,5′-diyl)bis(diphenylphosphane) |
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| OtherNames = SEGPHOS<br/>5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 244261-66-3 |
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| CASNo = 244261-66-3 |
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| CASOther = (R)<br/> (S) |
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| CASNo_Comment = (''R'') |
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| PubChem = |
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| CASNo2_Ref = {{cascite|changed|??}} |
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| SMILES = |
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| CASNo2 = 210169-54-3 |
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| CASNo2_Comment = (''S'') |
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| PubChem = 11017510 |
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| PubChem_Comment = (''RS'') |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 9192694 |
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| ChemSpiderID_Comment = (''RS'') |
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| SMILES = C1OC2=C(O1)C(=C(C=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)C5=C(C=CC6=C5OCO6)P(C7=CC=CC=C7)C8=CC=CC=C8 |
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| SMILES_Comment = (''RS'') |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C38H28O4P2/c1-5-13-27(14-6-1)43(28-15-7-2-8-16-28)33-23-21-31-37(41-25-39-31)35(33)36-34(24-22-32-38(36)42-26-40-32)44(29-17-9-3-10-18-29)30-19-11-4-12-20-30/h1-24H,25-26H2 |
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| StdInChI_Comment = (''RS'') |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = RZZDRSHFIVOQAF-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>38</sub>H<sub>28</sub>O<sub>4</sub>P<sub>2</sub> |
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| Formula = C<sub>38</sub>H<sub>28</sub>O<sub>4</sub>P<sub>2</sub> |
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| MolarMass = 610.57 g/mol |
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| MolarMass = 610.57 g/mol |
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| Appearance = colorless solid |
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| Appearance = colorless solid |
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| Density = |
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| Solubility = organic solvents |
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| Solubility = organic solvents |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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'''SEGPHOS''' is a ] ] that is used in ].<ref>{{cite journal | author = Shimizu, H., Nagasaki, I., Matsumura, K., Sayo, N., Saito, T. | title = Developments in Asymmetric Hydrogenation from an Industrial Perspective | year = 2007 | journal = ] | volume = 40 | issue = 12| pages = 1385–1393 | doi = 10.1021/ar700101x | pmid = 17685581 }}</ref> It was developed after ] and was investigated since it has a narrower dihedral angle between the aromatic faces. This was predicted and then confirmed to increase the enantioselectivity and activity of metal complexes of SEGPHOS. |
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'''SEGPHOS''' is a ] ] developed by ] that is used in ].<ref>{{cite journal | author = Shimizu, H., Nagasaki, I., Matsumura, K., Sayo, N., Saito, T. | title = Developments in Asymmetric Hydrogenation from an Industrial Perspective | year = 2007 | journal = ] | volume = 40 | issue = 12| pages = 1385–1393 | doi = 10.1021/ar700101x | pmid = 17685581 }}</ref> It was developed after ] and was investigated since it has a narrower dihedral angle between the aromatic faces. This was predicted and then confirmed to increase the enantioselectivity and activity of metal complexes of SEGPHOS. After its commercialization, SEGPHOS and its substituted derivatives have been found to constitute a privileged ligand class for a variety of transition metal catalysts and chemical transformations beyond its original application in ruthenium-catalyzed enantioselective hydrogenation. |
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In addition to the parent ligand bearing phenyl groups on the phosphorus atoms, the bulkier derivatives DM-SEGPHOS and DTBM-SEGPHOS are also commercially available.<ref>{{Cite web|url=http://www.strem.com/catalog/family/SEGPHOS/|title=SEGPHOS|website=www.strem.com|access-date=2016-08-10}}</ref> In DM-SEGPHOS and DTBM-SEGPHOS, the phenyl groups of SEGPHOS are replaced by 3,5-dimethylphenyl and 3,5-di-''tert''-butyl-4-methoxyphenyl groups, respectively. |
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According to Takasago, as BINAP is likened to a butterfly, SEGPHOS is like a seagull that "flies higher and faster" than a butterfly.<ref>{{Cite web|url=https://www.takasago.com/en/news/2002/0607_0528.html|title=Takasago Received The Molecular Chirality Awards 2002|website=Takasago International Corporation|language=en|access-date=2019-08-14}}</ref> Thus the ligand was named SE(A)G(ULL) + PHOS. |
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== References == |
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== References == |
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