(R(P),R(P))-1,2-bis[(2-benzyloxyphenyl)(phenyl)phosphino]ethane | 1064156-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R(P),R(P))-1,2-bis[(2-benzyloxyphenyl)(phenyl)phosphino]ethane
• 英文别名: Bn-SMS-Phos；(R,R)-1,2-bis[phenyl-(2-benzyloxy-phenyl) phosphino]ethane；(R)-phenyl-(2-phenylmethoxyphenyl)-[2-[phenyl-(2-phenylmethoxyphenyl)phosphanyl]ethyl]phosphane
• CAS: 1064156-63-3
• 化学式: C₄₀H₃₆O₂P₂
• 分子量: 610.672
• InChiKey: DPCRESQSMHPWNM-NDOUMJCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R(P),R(P))-1,2-bis[(2-benzyloxyphenyl)(phenyl)phosphino]ethane 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以70%的产率得到(R(P),R(P))-1,2-bis[(2-benzyloxyphenyl)(phenyl)phosphino-P-borane]ethane
  参考文献：
  名称：

  WO2008/117054

  摘要：

  公开号：
• 作为产物：
  描述：

  (R(P),R(P))-1,2-bis[(2-benzyloxyphenyl)(phenyl)phosphino-P-borane]ethane 在 二乙胺 作用下， 以98%的产率得到(R(P),R(P))-1,2-bis[(2-benzyloxyphenyl)(phenyl)phosphino]ethane
  参考文献：
  名称：

  Impact on Hydrogenation Catalytic Cycle of the R Groups’ Cyclic Feature in “R-SMS-Phos”

  摘要：

  A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ee's also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.

  DOI：

  10.1021/ol101029s

文献信息

• Profiling the tuneable R-SMS-Phos structure in the rhodium(i)-catalyzed hydrogenation of olefins: the last stand?
  作者：Michel Stephan、Damjan Šterk、Borut Zupančič、Barbara Mohar

  DOI：10.1039/c1ob05364g

  日期：——

  “R-SMS-Phos” R-SMS-Phos = 1,2-bis[(o-RO-phenyl)(phenyl)phosphino]ethane} ligands wherein R = branched or heteroatom-substituted alkyl, aralkyl, silyl, acyl, sulfonyl, etc. was screened for the Rh(I)-catalyzed hydrogenation of a representative set of olefinic substrates. This systematic and detailed investigation revealed a marked beneficial impact on enantioselectivity and catalyst activity in comparison

  对映体纯的P-立体异构“ R-SMS-Phos” R-SMS-Phos = 1,2-双[（邻-RO-苯基）（苯基）膦基]乙烷}配体的多样化家族，其中R =支链或杂原子-筛选取代的烷基，芳烷基，甲硅烷基，酰基，磺酰基等以用于Rh（I）催化的代表性烯烃底物组的氢化。与诺尔斯的最终DiPAMP DiPAMP =1,2-双[（邻茴香基）（苯基）膦基]乙烷} 设计。鉴定了具有高度增强的特性的突变体配体，这些突变体具有特定的特征，其中发现DiPAMP结构被嵌入。
• CHIRAL PHOSPHOROUS COMPOUNDS
  申请人：Gilheany Declan

  公开号：US20100168456A1

  公开（公告）日：2010-07-01

  The present invention provides P-chiral compounds of general formulae (II) and (III): in formula (II) at least one of R 21 , R 25 , R 26 and R 30 is independently selected from CM alkyl, CF 3 , C 1-4 alkoxy, phenyl and benzyloxy and the remaining substituents selected from R 21 , R 25 , R 26 and R 30 are hydrogen; at least one of R 22, R 24, R 27 and R 29 are independently selected from C 1-14 alkyl, CF 3, C 1-14 alkoxy, phenyl and benzyloxy and the remaining substituents selected, from R 22 , R 24, R 27 and R 29 are hydrogen; and R 23 and R28 are independently selected from hydrogen, CM alkyl, CF 3 , C 1-14 alkoxy, phenyl and benzyloxy; in formula (III) at least one of R 21 , R 25 , R 26 and R 30 is independently selected from phenyl and benzyloxy and the remaining substituents selected from R 21 , R 25 , R— 26 and R 30 are hydrogen; and R 22 , R— 23 R 24, R 27 , R 28 and R 29 are independently selected from hydrogen, C 1-14 alkyl, CF 3 , C 1-14 alkoxy, phenyl and benzyloxy.

  本发明提供了一般式（II）和（III）的P-手性化合物：在式（II）中，R21、R25、R26和R30中至少有一个是独立选择的CM烷基，CF3，C1-4烷氧基，苯基和苄氧基，其余取代基选择自R21、R25、R26和R30为氢；R22、R24、R27和R29中至少有一个是独立选择的C1-14烷基，CF3，C1-14烷氧基，苯基和苄氧基，其余取代基选择自R22、R24、R27和R29为氢；R23和R28独立选择自氢，CM烷基，CF3，C1-14烷氧基，苯基和苄氧基；在式（III）中，R21、R25、R26和R30中至少有一个是独立选择的苯基和苄氧基，其余取代基选择自R21、R25、R-26和R30为氢；R22、R-23、R24、R27、R28和R29独立选择自氢，C1-14烷基，CF3，C1-14烷氧基，苯基和苄氧基。
• US8067642B2
  申请人：——

  公开号：US8067642B2

  公开（公告）日：2011-11-29
• WO2008/117054
  申请人：——

  公开号：——

  公开（公告）日：——
• Impact on Hydrogenation Catalytic Cycle of the R Groups’ Cyclic Feature in “R-SMS-Phos”
  作者：Borut Zupančič、Barbara Mohar、Michel Stephan

  DOI：10.1021/ol101029s

  日期：2010.7.2

  A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ee's also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.