(1R,3R)-1-amino-3-(4-oct-1-ynyl-phenyl)-cyclopentanecarboxylic acid methyl ester | 1036386-92-1

• 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: (1R,3R)-1-amino-3-(4-oct-1-ynyl-phenyl)-cyclopentanecarboxylic acid methyl ester
• 英文别名: methyl (1R,3R)-1-amino-3-(4-oct-1-ynylphenyl)cyclopentane-1-carboxylate
• CAS: 1036386-92-1
• 化学式: C₂₁H₂₉NO₂
• 分子量: 327.467
• InChiKey: BLAFXHBSWNCFKW-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3R)-1-amino-3-(4-oct-1-ynyl-phenyl)-cyclopentanecarboxylic acid methyl ester 、 溶剂黄146 在 palladium 10% on activated carbon 、 氢气 作用下， 反应 72.0h， 生成 methyl (1R,3R)-1-amino-3-(4-octylphenyl)cyclopentanecarboxylate acetic acid salt
  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：

  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

文献信息

• Sphingosine-1-phosphate receptor agonist and antagonist compounds
  申请人：Wallace Grier A.

  公开号：US20090029947A1

  公开（公告）日：2009-01-29

  The present invention is directed to novel, potent, and selective agents, which are agonists or antagonists of the one or more of the individual receptors of the S1P receptor family. The compounds of the invention are useful as therapeutics for treating medical conditions associated with agonism or antagonism of the individual receptors of the S1P receptor family.

  本发明涉及一种新型、有效和选择性的药剂，它们是S1P受体家族中一个或多个单个受体的激动剂或拮抗剂。本发明的化合物可用作治疗与S1P受体家族中单个受体的激动或拮抗有关的医学状况的治疗剂。
• US8217027B2
  申请人：——

  公开号：US8217027B2

  公开（公告）日：2012-07-10
• 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
  作者：Grier A. Wallace、Thomas D. Gordon、Martin E. Hayes、Donald B. Konopacki、Shannon R. Fix-Stenzel、Xiaolei Zhang、Pintipa Grongsaard、Kevin P. Cusack、Lisa M. Schaffter、Rodger F. Henry、Robert H. Stoffel

  DOI：10.1021/jo900376b

  日期：2009.7.3

  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.