methyl (1R,3R)-1-amino-3-(4-bromophenyl)cyclopentanecarboxylate hydrochloride | 1036030-33-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1R,3R)-1-amino-3-(4-bromophenyl)cyclopentanecarboxylate hydrochloride
• 英文别名: (1R,3R)-1-amino-3-(4-bromo-phenyl)-cyclopentanecarboxylic acid methyl ester hydrochloride；Methyl (1R,3R)-1-amino-3-(4-bromophenyl)cyclopentane-1-carboxylate hcl；methyl (1R,3R)-1-amino-3-(4-bromophenyl)cyclopentane-1-carboxylate;hydrochloride
• CAS: 1036030-33-7
• 化学式: C₁₃H₁₆BrNO₂*ClH
• 分子量: 334.64
• InChiKey: DXLOKEVVKYIAPJ-HTMVYDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-辛炔 、 methyl (1R,3R)-1-amino-3-(4-bromophenyl)cyclopentanecarboxylate hydrochloride 在 哌啶 、 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 以90%的产率得到(1R,3R)-1-amino-3-(4-oct-1-ynyl-phenyl)-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Scalable Synthesis and Isolation of the Four Stereoisomers of Methyl 1-Amino-3-(4-bromophenyl)cyclopentanecarboxylate, Useful Intermediates for the Synthesis of S1P1 Receptor Agonists

  摘要：

  The individual isomers of methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate are useful intermediates for the synthesis of SIPI receptor agonists. Herein we describe a scalable synthesis and isolation of each of the four stereoisomers of this compound in gram quantities with >98% ee and de. The utility of this approach is demonstrated by the synthesis of ((1R,3R)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol in 7 steps, 11% overall yield, and >98% ee and de.

  DOI：

  10.1021/jo900376b
• 作为产物：
  描述：

  甲醇 、 (1R,3R)-1-氨基-3-(4-溴苯基)环戊烷羧酸盐酸盐 在 氯化亚砜 作用下， 以86%的产率得到methyl (1R,3R)-1-amino-3-(4-bromophenyl)cyclopentanecarboxylate hydrochloride
  参考文献：
  名称：

  Scalable Synthesis and Isolation of the Four Stereoisomers of Methyl 1-Amino-3-(4-bromophenyl)cyclopentanecarboxylate, Useful Intermediates for the Synthesis of S1P1 Receptor Agonists

  摘要：

  The individual isomers of methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate are useful intermediates for the synthesis of SIPI receptor agonists. Herein we describe a scalable synthesis and isolation of each of the four stereoisomers of this compound in gram quantities with >98% ee and de. The utility of this approach is demonstrated by the synthesis of ((1R,3R)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol in 7 steps, 11% overall yield, and >98% ee and de.

  DOI：

  10.1021/jo900376b

文献信息

• WO2008/79382
  申请人：——

  公开号：——

  公开（公告）日：——