(1R,2S)-cis-N-allyl-2-hydroxycyclopentanecarboxamide | 225791-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-cis-N-allyl-2-hydroxycyclopentanecarboxamide
• 英文别名: (1R,2S)-2-hydroxy-N-prop-2-enylcyclopentane-1-carboxamide
• CAS: 225791-06-0
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: OMZTZAFHYAGOIC-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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,2S)-cis-N-allyl-2-hydroxycyclopentanecarboxamide 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 40.0h， 生成 (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：

  N-allyl-2-oxocyclopentanecarboxamide 以 乙醇 为溶剂， 反应 96.0h， 以15%的产率得到(1S,2S)-trans-N-allyl-2-hydroxycyclopentanecarboxamide
  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.