(1R,cis)-3-aminomethyl-1,2,2-trimethylcyclopentylmethanol | 156767-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,cis)-3-aminomethyl-1,2,2-trimethylcyclopentylmethanol
• 英文别名: (1R,3S)-3-aminomethyl-1,2,2-trimethylcyclopentylmethanol；Cyclopentanemethanol, 3-(aminomethyl)-1,2,2-trimethyl-, (1R,3S)-；[(1R,3S)-3-(aminomethyl)-1,2,2-trimethylcyclopentyl]methanol
• CAS: 156767-18-9
• 化学式: C₁₀H₂₁NO
• 分子量: 171.283
• InChiKey: PUCMHUJJNLSQNC-SCZZXKLOSA-N

物化性质

• 沸点：
  242.8±13.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

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：

  (1R,cis)-3-aminomethyl-1,2,2-trimethylcyclopentylmethanol 在 盐酸 、 氨 、 三乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 146.0h， 生成 (1R,cis)-3-(6-amino-9H-purin-9-ylmethyl)-1,2,2-trimethylcyclopentylmethanol
  参考文献：
  名称：

  Synthesis, Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. Part 2:¹Adenosine and Uridine Analogues

  摘要：

  Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 5-7), 8-azapurine (compounds 9 and 10) or pyrimidine (compound 13) base on the amino group of (1R,cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2). The antiviral activity of compounds 5-7, 10 and 13, and their cytostatic activity, were evaluated. At subtoxic concentrations, the compounds showed no or marginal antiviral activity. Compound 5 showed moderate inhibition on tumor cell proliferation.

  DOI：

  10.1080/07328319808004237
• 作为产物：
  描述：

  methyl (1R,cis)-3-acetaminomethyl-1,2,2-trimethylcyclopentanecarboxylate 在 盐酸 、 sodium tetrahydroborate 、 Amberlite IRA-400 resin OH(-) form 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 (1R,cis)-3-aminomethyl-1,2,2-trimethylcyclopentylmethanol
  参考文献：
  名称：

  Synthesis of (1R, cis)-3-aminomethyl-1,2,2-trimethylcyclopentane-methanol: Two approaches using α-camphidone

  摘要：

  (IR)-alpha-camphidone has proved to be extremely resistant to alkaline and acid hydrolysis, but the latter can be accomplished under drastic conditions. The aminoacid so obtained was transformed into the aminoalcohol 3, a desirable intermediate in the synthesis of carbocyclic nucleoside analogues. Alternatively, the N-tosyl derivative of alpha-camphidone can be reductively cleaved under mild conditions and the resulting tosylaminoalcohol converted into 3 in good yield.

  DOI：

  10.1016/s0040-4020(01)85077-8

文献信息

• Carbocyclic Nucleosides with a Modified Cyclopentane Skeleton
  作者：O. Caamaño、F. Fernández、G. Gómez、M. I. Nieto

  DOI：10.1080/15257779508012365

  日期：1995.5.1

  The aminoalcohol 4 has been converted into carbocyclic nucleoside analogues 2 and 3.
• Synthesis and Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. I: Guanosine Analogues
  作者：J. M. Blanco、O. Caamaño、F. Fernández、G. Gómez、M. I. Nieto、J. Balzarini、E. Padalko、E. De Clercq

  DOI：10.1080/07328319708002530

  日期：1997.1

  Six new carbocyclic nucleosides were prepared by constructing a guanine (compounds 6, 8 and 10) or 8-azaguanine (compounds 7, 9 and 11) base on the amino group of (1R, cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2), and their activities against 13 viruses and 3 tumor cell lines were determined. Compounds 9, 10 and 11 showed activity against human immunodeficiency virus type 1 (HIV-1), and compound 11 also against vaccina virus, whereas compounds 6 and 7 showed some inhibition of tumor cell proliferation.
• Synthesis, Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclopentane Ring. Part 2:¹Adenosine and Uridine Analogues
  作者：M. I. Nieto、J. M. Blanco、O. CaamañTo、F. Fernández、X. García-Mera、J. Balzarini、E. Padalko、J. Neyts、E. De Clercq

  DOI：10.1080/07328319808004237

  日期：1998.7

  Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 5-7), 8-azapurine (compounds 9 and 10) or pyrimidine (compound 13) base on the amino group of (1R,cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2). The antiviral activity of compounds 5-7, 10 and 13, and their cytostatic activity, were evaluated. At subtoxic concentrations, the compounds showed no or marginal antiviral activity. Compound 5 showed moderate inhibition on tumor cell proliferation.
• Synthesis of (1R, cis)-3-aminomethyl-1,2,2-trimethylcyclopentane-methanol: Two approaches using α-camphidone
  作者：Olga Caamaño、Franco Fernández、Generosa Gómez、Isabel Nieto

  DOI：10.1016/s0040-4020(01)85077-8

  日期：1994.2

  (IR)-alpha-camphidone has proved to be extremely resistant to alkaline and acid hydrolysis, but the latter can be accomplished under drastic conditions. The aminoacid so obtained was transformed into the aminoalcohol 3, a desirable intermediate in the synthesis of carbocyclic nucleoside analogues. Alternatively, the N-tosyl derivative of alpha-camphidone can be reductively cleaved under mild conditions and the resulting tosylaminoalcohol converted into 3 in good yield.