(R,R)-(+)-1-benzyl-1-r-oxo-2-c,5-t-diphenylphospholane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,R)-(+)-1-benzyl-1-r-oxo-2-c,5-t-diphenylphospholane
• 英文别名: (2R,5R)-1-benzyl-2,5-diphenyl-1λ5-phospholane 1-oxide
• 化学式: C₂₃H₂₃OP
• 分子量: 346.409
• InChiKey: GSHGCQXUDNGQRE-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R,R)-(+)-1-benzyl-1-r-oxo-2-c,5-t-diphenylphospholane 在 poly-ε-carbobenzyloxy-L-lysine 作用下， 以 氯仿 为溶剂， 生成 (S,S)-(-)-1-benzyl-1-r-oxo-2-c,5-t-diphenylphospholane
  参考文献：
  名称：

  Efficient enantiodiscrimination of chiral monophosphine oxides and boranes by phosphorus coupled 13C NMR spectroscopy in the presence of chiral ordering agents

  摘要：

  The synthesis of new chiral phospholanes via the corresponding oxides or boranes is reported and the analytical potential of C-13-{H-1} NMR spectroscopy in weakly ordering polypeptide liquid crystalline phases in view to differentiate between enantiomers of these chiral phosphines precursors is explored. In particular results involving organic solutions of poly-gamma-benzyl-L-glutamate (PBLG) and poly-epsilon-carbobenzyloxy-L-lysine (PCBLL) are described. This NMR approach allows determination of the enantiomeric composition, and provides therefore a new efficient alternative to classical methods usually used to analyze this class of compounds. A description of various spectral enantiodifferentiation patterns expected to be observed using C-13-{H-1} NMR of enantiomers having a spin-1/2 heteroatomic nucleus, embedded in a chiral liquid crystal is presented. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00202-7
• 作为产物：
  描述：

  1,4-二苯基-1,3丁二烯 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 三氯化铝 、 草酰氯 、 乙二胺四乙酸 、 甲基锂 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， -78.0~20.0 ℃ 、5.0 MPa 条件下， 反应 70.0h， 生成 (R,R)-(+)-1-benzyl-1-r-oxo-2-c,5-t-diphenylphospholane
  参考文献：
  名称：

  手性单膦配体新家族的合成与首次应用：2,5-二苯基磷膦酸酯

  摘要：

  环状次膦酸1-羟基-1- [R -氧代- 2 Ç，5-吨-diphenylphospholane合成并通过奎宁盐的分级结晶拆分成的对映体。该P -苯基，P -甲基和P -苄基叔膦氧化物从二次膦氧化物得到，还原，得到相应的叔氧化物的P -苯基和P -苄基膦。前手性酰胺的氢化反应用Rh /（S，S）-1-1,2c ，5-叔三苯基膦烷催化体系进行。甲基（Z）-氢化N-乙酰基脱氢肉桂酸酯，得到93％ee的N-乙酰基苯丙氨酸酯。

  DOI：

  10.1016/s0040-4020(02)00554-9

文献信息

• Efficient enantiodiscrimination of chiral monophosphine oxides and boranes by phosphorus coupled 13C NMR spectroscopy in the presence of chiral ordering agents
  作者：Michaël Rivard、Frédéric Guillen、Jean-Claude Fiaud、Christie Aroulanda、Philippe Lesot

  DOI：10.1016/s0957-4166(03)00202-7

  日期：2003.5

  The synthesis of new chiral phospholanes via the corresponding oxides or boranes is reported and the analytical potential of C-13-H-1} NMR spectroscopy in weakly ordering polypeptide liquid crystalline phases in view to differentiate between enantiomers of these chiral phosphines precursors is explored. In particular results involving organic solutions of poly-gamma-benzyl-L-glutamate (PBLG) and poly-epsilon-carbobenzyloxy-L-lysine (PCBLL) are described. This NMR approach allows determination of the enantiomeric composition, and provides therefore a new efficient alternative to classical methods usually used to analyze this class of compounds. A description of various spectral enantiodifferentiation patterns expected to be observed using C-13-H-1} NMR of enantiomers having a spin-1/2 heteroatomic nucleus, embedded in a chiral liquid crystal is presented. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and first applications of a new family of chiral monophosphine ligand: 2,5-diphenylphosphospholanes
  作者：Frédéric Guillen、Michael Rivard、Martial Toffano、Jean-Yves Legros、Jean-Claude Daran、Jean-Claude Fiaud

  DOI：10.1016/s0040-4020(02)00554-9

  日期：2002.7

  The cyclic phosphinic acid 1-hydroxy-1-r-oxo-2c,5-t-diphenylphospholane was synthesized and resolved into enantiomers through fractional crystallization of the quinine salts. The P-phenyl, P-methyl and P-benzyl tertiary phosphine oxides were obtained from the secondary phosphine oxide, reduction of the oxides afforded the corresponding tertiary P-phenyl and P-benzyl phosphines. Hydrogenation of prochiral

  环状次膦酸1-羟基-1- [R -氧代- 2 Ç，5-吨-diphenylphospholane合成并通过奎宁盐的分级结晶拆分成的对映体。该P -苯基，P -甲基和P -苄基叔膦氧化物从二次膦氧化物得到，还原，得到相应的叔氧化物的P -苯基和P -苄基膦。前手性酰胺的氢化反应用Rh /（S，S）-1-1,2c ，5-叔三苯基膦烷催化体系进行。甲基（Z）-氢化N-乙酰基脱氢肉桂酸酯，得到93％ee的N-乙酰基苯丙氨酸酯。