(1S,3R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol | 211613-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol
• 英文别名: [(1S,3R)-3-(aminomethyl)-2,2,3-trimethylcyclopentyl]methanol
• CAS: 211613-90-0
• 化学式: C₁₀H₂₁NO
• 分子量: 171.283
• InChiKey: CQZOJWWNJASHIC-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol 在 盐酸 、 sodium hydroxide 、 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 95.5h， 生成 9-((1R,3S)-3-Hydroxymethyl-1,2,2-trimethyl-cyclopentylmethyl)-9H-purin-6-ol
  参考文献：
  名称：

  SYNTHESIS, ANTIVIRAL AND CYTOSTATIC ACTIVITIES, OF CARBOCYCLIC NUCLEOSIDES INCORPORATING A MODIFIED CYCLOPENTANE RING. IV. ADENOSINE AND URIDINE ANALOGUES

  摘要：

  Eight new carbocyclic nucleosides were prepared by mounting a purine (compounds 8-10), 8-azapurine (12 and 13) or pyrimidine (15, 16 and 17b) on the amino group of (1S,3R)-3-aminomethyl-2,2,3-trimethyl-cyclopentylmethanol (6). All the compounds were evaluated as antiviral and antitumor agents in a variety of assay systems. Only compound 8 showed any cytostatic activity against the tumor cell lines examined.

  DOI：

  10.1081/ncn-120003289
• 作为产物：
  描述：

  (1R)-cis-camphoric acid-3-methyl ester-1-amide 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (1S,3R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol
  参考文献：
  名称：

  由（+）-樟脑酸合成（1 S，3 R）-3-氨基甲基-2,2,3-三甲基环戊基甲醇和（1 S，3 R）-3-氨基-2,2,3-三甲基环戊基甲醇的合成方法

  摘要：

  标题氨基甲基（5）和氨基（6）醇，作为合成核苷碳环类似物的中间体，是由（+）-樟脑酸经甲基（1 S，3 R）-3-氨基甲酰基制备的-2,3,3-三甲基环戊烷羧酸酯（8）。直接还原8可得到5，收率26％。氨基醇6通过几种方法以11–53％的总收率制备，每种方法都涉及8的氧化降解，然后进行还原步骤。

  DOI：

  10.1016/s0040-4020(98)00416-5

文献信息

• Synthetic approaches to (1S,3R)-3-aminomethyl-2,2,3-trimethylcyclopentylmethanol and (1S,3R)-3-amino-2,2,3-trimethylcyclopentylmethanol from (+)-camphoric acid
  作者：María I. Nieto、JoséM. Blanco、Olga Caamaño、Franco Fernández、Generosa Gómez

  DOI：10.1016/s0040-4020(98)00416-5

  日期：1998.7

  The title aminomethyl (5) and amino (6) alcohols, which are of interest as intermediates in the synthesis of carbocyclic analogues of nucleosides, were prepared from (+)-camphoric acid via methyl (1S,3R)-3-carbamoyl-2,3,3-trimethylcyclopentane carboxylate (8). Direct reduction of 8 gave 5 in 26% yield. Amino alcohol 6 was prepared in 11–53% overall yields by several approaches, each involving oxidative

  标题氨基甲基（5）和氨基（6）醇，作为合成核苷碳环类似物的中间体，是由（+）-樟脑酸经甲基（1 S，3 R）-3-氨基甲酰基制备的-2,3,3-三甲基环戊烷羧酸酯（8）。直接还原8可得到5，收率26％。氨基醇6通过几种方法以11–53％的总收率制备，每种方法都涉及8的氧化降解，然后进行还原步骤。
• SYNTHESIS, ANTIVIRAL AND CYTOSTATIC ACTIVITIES, OF CARBOCYCLIC NUCLEOSIDES INCORPORATING A MODIFIED CYCLOPENTANE RING. IV. ADENOSINE AND URIDINE ANALOGUES
  作者：M. Isabel Nieto、Olga Caamaño、Franco Fernández、María Gómez、Jan Balzarini、Erik De Clercq

  DOI：10.1081/ncn-120003289

  日期：2002.4.15

  Eight new carbocyclic nucleosides were prepared by mounting a purine (compounds 8-10), 8-azapurine (12 and 13) or pyrimidine (15, 16 and 17b) on the amino group of (1S,3R)-3-aminomethyl-2,2,3-trimethyl-cyclopentylmethanol (6). All the compounds were evaluated as antiviral and antitumor agents in a variety of assay systems. Only compound 8 showed any cytostatic activity against the tumor cell lines examined.