(R_p)-[(tert-butyl)(phenyl)phosphinoyl]acetic acid menthyl ester | 98933-82-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R_p)-[(tert-butyl)(phenyl)phosphinoyl]acetic acid menthyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-[tert-butyl(phenyl)phosphoryl]acetate
• CAS: 98933-82-5
• 化学式: C₂₂H₃₅O₃P
• 分子量: 378.492
• InChiKey: NCJOPZKIMRPEOY-AQZHHXFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R_p)-[(tert-butyl)(phenyl)phosphinoyl]acetic acid menthyl ester 在 4-二甲氨基吡啶 、 氢氧化钾 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (Rp,1S)-2-[(tert-butyl)(phenyl)phosphinoyl]-N-[1-(hydroxymethyl)-2-methylpropyl]acetamide
  参考文献：
  名称：

  Aminohydroxy phosphine oxide ligands in ruthenium-catalysed asymmetric transfer hydrogenation reactions

  摘要：

  A class of aminohydroxy phosphine oxide ligands was derived from optically active amino alcohols, containing stereogenic centres at phosphorus and at carbon. Their activities and selectivities in the asymmetric transfer hydrogenation reaction were assessed, including match and mismatch of chiralities. Enantioselectivities of more than 92% were achieved in the reduction of acetophenone and propiophenone under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.040
• 作为产物：
  描述：

  苯膦酰二氯 在 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 43.0h， 生成 (R_p)-[(tert-butyl)(phenyl)phosphinoyl]acetic acid menthyl ester
  参考文献：
  名称：

  Aminohydroxy phosphine oxide ligands in ruthenium-catalysed asymmetric transfer hydrogenation reactions

  摘要：

  A class of aminohydroxy phosphine oxide ligands was derived from optically active amino alcohols, containing stereogenic centres at phosphorus and at carbon. Their activities and selectivities in the asymmetric transfer hydrogenation reaction were assessed, including match and mismatch of chiralities. Enantioselectivities of more than 92% were achieved in the reduction of acetophenone and propiophenone under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.040

文献信息

• A new method for the synthesis of optically pure phosphine oxides
  作者：Tsuneo Imamoto、Kazuhiko Sato、Carl R. Johnson

  DOI：10.1016/s0040-4039(00)89136-4

  日期：1985.1

  Tertiary phosphine oxides have been prepared with high enantiomeric excesses via intermediate menthyl 2-phosphinylacetates.

  叔膦氧化物已通过中间体2-次膦酰基乙酸薄荷酯以高对映体过量的形式制备。