(+/-)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide | 2799-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide
• 英文别名: (1R,2S)-N-benzyl-2-hydroxycyclopentane-1-carboxamide
• CAS: 2799-87-3；100804-46-4
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: VGAPGWOAAWDGTK-NEPJUHHUSA-N

物化性质

• 熔点：
  141 °C
• 沸点：
  459.6±44.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (+/-)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以87%的产率得到(1S,2S)-2-[(benzylamino)methyl]cyclopentan-1-ol
  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,2R)-2-hydroxycyclopentane-1-carboxylic acid 、 苄胺 反应 2.0h， 以69%的产率得到(+/-)-cis-N-benzyl-2-hydroxycyclopentanecarboxamide
  参考文献：
  名称：

  Stereochemical studies, 73. Saturated heterocycles, 60

  摘要：

  DOI：

  10.1007/bf00809162

文献信息

• The first asymmetric ring-expansion carbonylation of meso-epoxides
  作者：Prasad Ganji、Hasim Ibrahim

  DOI：10.1039/c2cc35596e

  日期：——

  The first asymmetric ring-expansion carbonylation of meso-epoxides to β-lactones is reported. Two structurally diverse chiral Cr(III) chloro complexes in conjunction with Co2(CO)8 were shown to be competent catalytic systems for this transformation, displaying significant levels of asymmetric induction of up to 56% ee.

  首次报道了介环氧化物与 β-内酯的不对称扩环羰基化反应。研究表明，两种结构不同的手性铬(III)氯配合物与 Co2(CO)8 共同组成的催化体系能够胜任这一转化过程，并显示出高达 56% ee 的显著不对称诱导水平。
• PINTYE, J.;FUELOEP, F.;BERNATH, G.;SOHAR, P., MONATSH. CHEM., 1985, 116, N 6-7, 857-868
  作者：PINTYE, J.、FUELOEP, F.、BERNATH, G.、SOHAR, P.

  DOI：——

  日期：——
• PINTYE, J.;FUELOEP, F.;BERNATH, G.;SOHAR, P., MAGY. KEM. FOLYOIRAT, 1985, 91, N 7, 301-307
  作者：PINTYE, J.、FUELOEP, F.、BERNATH, G.、SOHAR, P.

  DOI：——

  日期：——
• Stereochemical studies, 73. Saturated heterocycles, 60
  作者：J�nos Pintye、Ferenc F�l�p、G�bor Bern�th、P�l Soh�r

  DOI：10.1007/bf00809162

  日期：——
• 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.