(R*,S*)-2-Diphenylphosphinoyl-1-cyclohexylpropan-1-ol | 88533-71-5

• 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*,S*)-2-Diphenylphosphinoyl-1-cyclohexylpropan-1-ol
• 英文别名: (1S,2R)-1-cyclohexyl-2-diphenylphosphorylpropan-1-ol
• CAS: 88533-71-5；88533-79-3；103786-03-4；103786-04-5
• 化学式: C₂₁H₂₇O₂P
• 分子量: 342.418
• InChiKey: NOVOHWNLJMKRPP-DYESRHJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R*,S*)-2-Diphenylphosphinoyl-1-cyclohexylpropan-1-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79.1%的产率得到(Z)-prop-1-en-1-ylcyclohexane
  参考文献：
  名称：

  Buss, Antony D.; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2307 - 2326

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基二苯基氧化膦 在 锂硼氢 、 正丁基锂 、 tetramethylpiperidine 、 四氯化钛 作用下， 反应 6.0h， 生成 (R*,S*)-2-Diphenylphosphinoyl-1-cyclohexylpropan-1-ol
  参考文献：
  名称：

  的TiCl 4介导的LiBH 4还原β-ketophosphine氧化物：以合成的高立体选择性路线抗- β -hydroxyphosphine氧化物

  摘要：

  在强螯合剂（例如TiCl 4）存在下，用LiBH 4还原α-烷基-β-酮膦氧化物，可以独立于两者的大小，以高收率和高抗-非对映选择性生成相应的β-羟基膦氧化物。α-和β-烷基链。

  DOI：

  10.1016/0040-4039(96)01601-2

文献信息

• TiCl4 Mediated LiBH4 reduction of β-ketophosphine oxides: a high stereoselective route to the synthesis of anti-β-hydroxyphosphine oxides
  作者：Giuseppe Bartoli、Marcella Bosco、Letizia Sambri、Enrico Marcantoni

  DOI：10.1016/0040-4039(96)01601-2

  日期：1996.10

  The reduction of an α-alkyl-β-ketophosphine oxide with LiBH4 in presence of a strong chelating agent, such as TiCl4, gives the corresponding β-hydroxyphosphine oxide in high yields and with high anti-diastereoselectivity independently from the size of both the α- and β-alkyl chains.

  在强螯合剂（例如TiCl 4）存在下，用LiBH 4还原α-烷基-β-酮膦氧化物，可以独立于两者的大小，以高收率和高抗-非对映选择性生成相应的β-羟基膦氧化物。α-和β-烷基链。
• Functionalized Phosphine Imides. Diastereoselective Synthesis of β-Hydroxyphosphorylated Derivatives
  作者：José Barluenga、Fernando López、Francisco Palacios

  DOI：10.1055/s-1988-27641

  日期：——

  The diastereoselective synthesis, of 2-hydroxyalkyldiphenylphosphine phenylimides 2 and oxides 3 by reaction of α-metallated phosphine imides with aldehydes is described. When dimethylformamide or dimethyl disulfide were used as electrophiles, functionalized phosphine imides 4 or 6 were obtained, respectively.

  本文介绍了通过δ-金属化膦酰亚胺与醛反应，非对映选择性合成 2-羟基烷基二苯基膦苯基亚胺 2 和氧化物 3 的方法。 当使用二甲基甲酰胺或二甲基二硫作为亲电体时，可分别得到官能化的膦酰亚胺 4 或 6。
• -olefins from the horner-wittig reaction; origin and optimisation of stereochemistry
  作者：Antony D. Buss、Stuart Warrne

  DOI：10.1016/s0040-4039(00)94318-1

  日期：1983.1
• Buss, Antony D.; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2307 - 2326
  作者：Buss, Antony D.、Warren, Stuart

  DOI：——

  日期：——
• Opposite Stereochemical Effects Exerted by CeCl3 and TiCl4 on the Lewis Acid Mediated Reduction of α-Alkyl-β-ketophosphine Oxides with Metallic Hydrides: A Highly Stereoselective Protocol for the Synthesis of syn and anti α-alkyl-β-Hydroxyphosphine Oxides
  作者：Giuseppe Bartoli、Marcella Bosco、Letizia Sambri、Renato Dalpozzo、Enrico Marcantoni

  DOI：10.1002/chem.19970031209

  日期：1997.12

  AbstractA general, highly efficient methodology for obtaining both syn and anti β‐hydroxyphosphine oxides by reduction of the corresponding β‐ketophosphine oxides is described. The nature of the Lewis acid was found to be pivotal in determining the outcome of these reactions. Strongly chelating TiCl4 led to the anti isomer in high diastereoisomeric excess in noncoordinating solvents (CH2Cl2) at ‐78°C with BH3/py as reducing agent, while nonchelating CeCl3 gave a high excess of the syn isomer in coordinating solvents (THF) at the same temperature with LiBH4 as reducing agent. In the latter case, CeCl3 is essential in achieving high yields and stereoselectivity, since it allows the reaction to be performed at low temperatures. Otherwise, higher temperatures (0°C) are required, which lower both yields and selectivities. Moreover, each step of the protocol for the synthesis of stereodefined disubstituted olefins from alkylphosphine oxides (Warren's modification of the Horner procedure) has been optimized, and the optimized procedure has been applied to the synthesis of muscalure, the pheromone of the domestic fly.