((1R,3R)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol hydrochloride | 1000807-57-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ((1R,3R)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol hydrochloride
• 英文别名: [(1R,3R)-1-amino-3-(4-octylphenyl)cyclopentyl]methanol;hydrochloride
• CAS: 1000807-57-7
• 化学式: C₂₀H₃₃NO*ClH
• 分子量: 339.949
• InChiKey: PNZRKESIGWPLIX-GZJHNZOKSA-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,3R)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol hydrochloride 在 焦磷酸 作用下， 以50%的产率得到((1R,3R)-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：

  methyl (1R,3R)-1-amino-3-(4-octylphenyl)cyclopentanecarboxylate acetic acid salt 在 碳酸氢钠 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 水 为溶剂， 以2.40 g的产率得到((1R,3R)-1-amino-3-(4-octylphenyl)cyclopentyl)methanol 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