{[(4S,5S)-5-[(diphenylphosphanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}diphenylphosphane

• ChemBase编号: 151503
• 分子式: C31H32O2P2
• 平均质量: 498.532102
• 单一同位素质量: 498.18775352
• SMILES: CC1(O[C@@H]([C@H](O1)CP(c1ccccc1)c1ccccc1)CP(c1ccccc1)c1ccccc1)C
• Canonical SMILES: CC1(C)O[C@@H]([C@H](O1)CP(c1ccccc1)c1ccccc1)CP(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C31H32O2P2/c1-31(2)32-29(23-34(25-15-7-3-8-16-25)26-17-9-4-10-18-26)30(33-31)24-35(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-22,29-30H,23-24H2,1-2H3/t29-,30-/m1/s1
• InChIKey: VCHDBLPQYJAQSQ-LOYHVIPDSA-N

名称和登记号

名称

• IUPAC标准名: {[(4S,5S)-5-[(diphenylphosphanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}diphenylphosphane
• IUPAC传统名: {[(4S,5S)-5-[(diphenylphosphanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}diphenylphosphane
• 别名: (+)-1,4-双(二苯基膦)-1,4-二脱氧-2,3-O-异亚丙基-D-苏糖醇; (4S,5S)-4,5-双(二苯基膦甲基)-2,2-二甲基-1,3-二氧戊环; (4S-反式)-[(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(亚甲基)]双(二苯基膦); (+)-2,3-O-异丙烯基-2,3-二羟基-1,4-双(二苯基膦)丁烷; (+)-异丙烯-2,3-二羟-1,4-双二丙基膦丁烷; (+)-DIOP; (S,S)-DIOP; (+)-1,4-Bis(diphenylphosphino)-1,4-dideoxy-2,3-O-isopropylidene-D-threitol; (4S,5S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane; (4S-trans)-[(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)]bis(diphenylphosphine); (+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; (+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; (+)-DIOP

登记号

• CAS号: 37002-48-5
• EC号: 253-307-9
• MDL号: MFCD00009760
• Beilstein号: 1630280
• PubChem SID: 24854262; 162245656
• PubChem CID: 3084647

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 7.4485
• LogD (pH = 7.4): 7.4485
• Log P: 7.4485
• 摩尔折射率: 145.9648 cm^3
• 极化性: 58.1516 Å^3
• 极化表面积: 18.46 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

分子性质

理化性质

• 熔点: 86-88 °C(lit.); 88-90°C
• 比旋光度: [α]19/D +26°, c = 2.3 in chloroform; +12.5 (c=4.6 in benzene)

安全信息

• 保存注意事项: Air Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26; 26-37
• TSCA收录: 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: 98%
• Empirical Formula (Hill Notation): C31H32O2P2

详细说明

Sigma Aldrich - 237663

Application
用于原位制备手性氢化催化剂。
配体，用于烯酰胺的 Rh(I) 催化不对称氢化反应、α,β-不饱和酮的 1,4-二硅基化反应、烯基碘化物的 Heck 反应以及烯烃的加氢甲酰化反应。
包装
1 g in glass bottle

参考文献

• Ligand for the in situ preparation of chiral hydrogenation catalysts: J. Am. Chem. Soc., 94, 6429 (1972); Helv. Chim. Acta, 57, 2487 (1974); J. Org. Chem., 44, 3741 (1979).