trans-(3,4-epoxycyclopentyl)dicyclopentylphosphine oxide | 455310-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: trans-(3,4-epoxycyclopentyl)dicyclopentylphosphine oxide
• CAS: 455310-85-7
• 化学式: C₁₅H₂₅O₂P
• 分子量: 268.336
• InChiKey: GWVAPAVGNSUHBP-QKDCVEJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-(3,4-epoxycyclopentyl)dicyclopentylphosphine oxide 在 potassium cyanide 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 29.0h， 生成 (+/-)-t-4-(dicyclopentylphosphinoyl)-t-2-[(diphenylphosphinoyl)methyl]-r-1-cyclopentanol
  参考文献：
  名称：

  Towards chiral non-racemic cis -1,3-disubstituted cyclopentane 1,4-diphosphines

  摘要：

  Reaction of dialkyl- or diaryl-trans-(3,4-epoxycyclopentyl)phosphine oxides 2 with the lithium derivative of methyldiphenylphosphine oxide gives a mixture of (+/-)-t-4- and (+/-)-c-4-(disubstituted phosphinoyl)-t-2-(diphenylphosphinoyl-methyl)-r-1-cyclopentanol derivatives 13a-c and 16a-c, which could be obtained in pure form by separation of the corresponding acetates 14a-c and 17a-c followed by methanolysis. Compounds 13b and 16b were transformed into the corresponding dehydroxy derivatives 19 and 21 through the Barton procedure. Additionally, 16a was transformed into a diastereomeric mixture of carbamates 22 and 23 on reaction with (S)-alpha-phenylethylisocyanate which could be separated by repeated crystallization. The relative configuration of compounds 13b, 17a, 21 and 22 was established by X-ray diffraction analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00184-2
• 作为产物：
  描述：

  3-(dicyclopentylphosphinoyl)cyclopentyl methane sulfonate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 20.0~120.0 ℃ 、66.66 Pa 条件下， 反应 30.0h， 以4.01 g的产率得到trans-(3,4-epoxycyclopentyl)dicyclopentylphosphine oxide
  参考文献：
  名称：

  Towards chiral non-racemic cis -1,3-disubstituted cyclopentane 1,4-diphosphines

  摘要：

  Reaction of dialkyl- or diaryl-trans-(3,4-epoxycyclopentyl)phosphine oxides 2 with the lithium derivative of methyldiphenylphosphine oxide gives a mixture of (+/-)-t-4- and (+/-)-c-4-(disubstituted phosphinoyl)-t-2-(diphenylphosphinoyl-methyl)-r-1-cyclopentanol derivatives 13a-c and 16a-c, which could be obtained in pure form by separation of the corresponding acetates 14a-c and 17a-c followed by methanolysis. Compounds 13b and 16b were transformed into the corresponding dehydroxy derivatives 19 and 21 through the Barton procedure. Additionally, 16a was transformed into a diastereomeric mixture of carbamates 22 and 23 on reaction with (S)-alpha-phenylethylisocyanate which could be separated by repeated crystallization. The relative configuration of compounds 13b, 17a, 21 and 22 was established by X-ray diffraction analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00184-2