[(R)-1-hydroxymethyl-3-(4-octylphenyl)cyclopent-3-enyl]carbamic acid tert-butyl ester | 1173893-45-2

• 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)-1-hydroxymethyl-3-(4-octylphenyl)cyclopent-3-enyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R)-1-(hydroxymethyl)-3-(4-octylphenyl)cyclopent-3-en-1-yl]carbamate
• CAS: 1173893-45-2
• 化学式: C₂₅H₃₉NO₃
• 分子量: 401.59
• InChiKey: PUYOOBBDPMSCHW-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(R)-1-hydroxymethyl-3-(4-octylphenyl)cyclopent-3-enyl]carbamic acid tert-butyl ester 在 5% Pd-BaSO4 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 16.0h， 生成 tert-butyl (1R,3S)-1-(hydroxymethyl)-3-(4-octylphenyl)cyclopentylcarbamate 、 tert-butyl (1R,3R)-1-(hydroxymethyl)-3-(4-octylphenyl)cyclopentylcarbamate
  参考文献：
  名称：

  A stereoselective and scalable synthesis of a conformationally constrained S1P1 agonist

  摘要：

  A scalable and enantioselective synthesis of a potent SIP1 agonist containing two stereogenic centers oil a cyclopentane ring is described. Control of the absolute chirality of an amino alcohol precursor, generated via a robust phase-transfer catalyzed alkylation protocol, allows for Substrate directed hydrogenation to install the second stereogenic center providing access to gram-quantities of compound 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.099
• 作为产物：
  描述：

  (R)-1-tert-butoxycarbonylamino-3-(4-octylphenyl)cyclopent-3-enecarboxylic acid tert-butyl ester 在 锂硼氢 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以87%的产率得到[(R)-1-hydroxymethyl-3-(4-octylphenyl)cyclopent-3-enyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  A stereoselective and scalable synthesis of a conformationally constrained S1P1 agonist

  摘要：

  A scalable and enantioselective synthesis of a potent SIP1 agonist containing two stereogenic centers oil a cyclopentane ring is described. Control of the absolute chirality of an amino alcohol precursor, generated via a robust phase-transfer catalyzed alkylation protocol, allows for Substrate directed hydrogenation to install the second stereogenic center providing access to gram-quantities of compound 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.099