(1S,2S)-cis-2-(N-propylaminomethyl)cyclopentanol | 225791-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-cis-2-(N-propylaminomethyl)cyclopentanol
• 英文别名: (1S,2S)-2-(propylaminomethyl)cyclopentan-1-ol
• CAS: 225791-10-6
• 化学式: C₉H₁₉NO
• 分子量: 157.256
• InChiKey: QBNFJRHVMVALCR-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-羰基二咪唑 、 (1S,2S)-cis-2-(N-propylaminomethyl)cyclopentanol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以72%的产率得到(4aS,7aS)-cis-propylperhydrocyclopenta-1,3-oxazin-2-one
  参考文献：
  名称：

  Bioreduction of 2-oxocyclopentanecarboxamides: syntheses of optically active 2-aminomethyl- and 2-aminocyclopentanols

  摘要：

  The fungus Mortierella isabellina NRRL 1757 catalyzes the reduction of 2-oxocyclopentanecarboxamides with very high enantioselectivity giving, in most cases, the corresponding enantiopure 2-hydroxycyclopentanecarboxamides. The presence or absence of a substituent on the amidic nitrogen has a strong influence on the diastereoselectivity achieved in these processes. Optically active hydroxyamides prepared in these microbial reductions are used as starting materials for the preparation of optically active 2-aminomethyl- and 2-aminocyclopentanols. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00016-6
• 作为产物：
  描述：

  (1S,2S)-2-[(benzylamino)methyl]cyclopentan-1-ol 在 palladium on activated charcoal lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 26.0h， 生成 (1S,2S)-cis-2-(N-propylaminomethyl)cyclopentanol
  参考文献：
  名称：

  Bioreduction of 2-oxocyclopentanecarboxamides: syntheses of optically active 2-aminomethyl- and 2-aminocyclopentanols

  摘要：

  The fungus Mortierella isabellina NRRL 1757 catalyzes the reduction of 2-oxocyclopentanecarboxamides with very high enantioselectivity giving, in most cases, the corresponding enantiopure 2-hydroxycyclopentanecarboxamides. The presence or absence of a substituent on the amidic nitrogen has a strong influence on the diastereoselectivity achieved in these processes. Optically active hydroxyamides prepared in these microbial reductions are used as starting materials for the preparation of optically active 2-aminomethyl- and 2-aminocyclopentanols. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00016-6

文献信息

• Bioreduction of 2-oxocyclopentanecarboxamides: syntheses of optically active 2-aminomethyl- and 2-aminocyclopentanols
  作者：Margarita Quirós、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/s0957-4166(99)00016-6

  日期：1999.2

  The fungus Mortierella isabellina NRRL 1757 catalyzes the reduction of 2-oxocyclopentanecarboxamides with very high enantioselectivity giving, in most cases, the corresponding enantiopure 2-hydroxycyclopentanecarboxamides. The presence or absence of a substituent on the amidic nitrogen has a strong influence on the diastereoselectivity achieved in these processes. Optically active hydroxyamides prepared in these microbial reductions are used as starting materials for the preparation of optically active 2-aminomethyl- and 2-aminocyclopentanols. (C) 1999 Elsevier Science Ltd. All rights reserved.