(1R,cis)-N-(3-hydroxymethyl-2,2,3-trimethylcyclopentylmethyl)acetamide | 156660-31-0

• 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,cis)-N-(3-hydroxymethyl-2,2,3-trimethylcyclopentylmethyl)acetamide
• 英文别名: N-[[(1S,3R)-3-(hydroxymethyl)-2,2,3-trimethylcyclopentyl]methyl]acetamide
• CAS: 156660-31-0
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: DDAWGWBIGMEVAN-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,cis)-N-(3-hydroxymethyl-2,2,3-trimethylcyclopentylmethyl)acetamide 在 盐酸 、 Amberlite IRA-400 resin OH(-) form 作用下， 以 甲醇 为溶剂， 反应 5.0h， 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
• 作为产物：
  描述：

  白樟油 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 三乙胺 、 hydroxylamine-O-sulfonic acid 作用下， 以 四氢呋喃 、 乙醚 、 水 、 溶剂黄146 为溶剂， 反应 388.5h， 生成 (1R,cis)-N-(3-hydroxymethyl-2,2,3-trimethylcyclopentylmethyl)acetamide
  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

• 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.