((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol hydrochloride | 1000807-56-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol hydrochloride
• 英文别名: [(1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl]methanol;hydrochloride
• CAS: 1000807-56-6
• 化学式: C₂₀H₃₃NO*ClH
• 分子量: 339.949
• InChiKey: PNZRKESIGWPLIX-CMXBXVFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol hydrochloride 在 焦磷酸 作用下， 反应 2.0h， 以56%的产率得到((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)methyl dihydrogen phosphate
  参考文献：
  名称：

  Asymmetric Synthesis of Conformationally Constrained Fingolimod Analogues—Discovery of an Orally Active Sphingosine 1-Phosphate Receptor Type-1 Agonist and Receptor Type-3 Antagonist

  摘要：

  Compound 1 (FTY720, Fingolimod) represents a new generation of immunosuppressant that modulates lymphocyte trafficking by interacting with the S1P(1) receptor. Compound 1 also provides a template molecule for studying the molecular biology of S1P receptors and related enzymes (kinases and phosphatases). In this study, two conformationally constrained analogues of 1 (3a and 3c) were asymmetrically synthesized in high optical purity. In vitro assessment documented that both analogues are Sphk2 substrates, their phosphorylated species are potent S1P(1) receptor agonists, and 3a-P is a potent SIP3 antagonist. After oral administration in mice, both compounds evoked lymphopenia, but their duration of action differed markedly.

  DOI：

  10.1021/jm7010172
• 作为产物：
  描述：

  (1R,3S)-1-amino-3-(4-octyl-phenyl)-cyclopentanecarboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 、 盐酸 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 ((1R,3S)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol hydrochloride
  参考文献：
  名称：

  WO2008/79382

  摘要：

  公开号：

文献信息

• A stereoselective and scalable synthesis of a conformationally constrained S1P1 agonist
  作者：Shannon R. Fix-Stenzel、Martin E. Hayes、Xiaolei Zhang、Grier A. Wallace、Pintipa Grongsaard、Lisa M. Schaffter、Steven M. Hannick、Thaddeus S. Franczyk、Robert H. Stoffel、Kevin P. Cusack

  DOI：10.1016/j.tetlet.2009.04.099

  日期：2009.7

  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.