(1R,2S)-2-(hydroxymethyl)-N-[(1R)-phenylethyl]-cyclopent-3-ene-1-carboxamide | 1040919-32-1

• 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: (1R,2S)-2-(hydroxymethyl)-N-[(1R)-phenylethyl]-cyclopent-3-ene-1-carboxamide
• 英文别名: (1R,2S)-2-hydroxymethyl-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide；(1r,2s)-2-(hydroxymethyl)-N-[(1r)-1-phenyl-ethyl]cyclopent-3-ene-1-carboxamide；(1R,2S)-2-(hydroxymethyl)-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamide
• CAS: 1040919-32-1
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: LETPTSFGZGSBLC-MRVWCRGKSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  466.6±44.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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)-2-(hydroxymethyl)-N-[(1R)-phenylethyl]-cyclopent-3-ene-1-carboxamide 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硫酸 、 水 、 三正丁基氢锡 作用下， 以 1,4-二氧六环 、 水 、 乙腈 、 苯 为溶剂， 反应 8.0h， 生成 (3aS,4R,6aR)-4-hydroxyhexahydro-1H-cyclopenta[c]furan-1-one
  参考文献：
  名称：

  Sarkomycin A methyl esters and functionalized cyclopentane blocks for brefeldin A

  摘要：

  Sarkomycin A methyl esters and functionalized cyclopentane blocks for brefeldin A were synthesized starting from diastereoisomeric (1R,2S)- and (1S,2R)-2-hydroxymethyl-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamides.

  DOI：

  10.1134/s1070428012010022
• 作为产物：
  描述：

  (3aS,6aR)-3R-hydroxy-2-[(1R)-phenylethyl]-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以89%的产率得到(1R,2S)-2-(hydroxymethyl)-N-[(1R)-phenylethyl]-cyclopent-3-ene-1-carboxamide
  参考文献：
  名称：

  Epoxy derivatives of {(5-[(1-Phenylethyl)aminocarbonyl]-cyclopent-2-en-1-yl}methyl acetates

  摘要：

  Diastereoisomeric [(1R,5S)-5-{[(1R)-1-phenylethyl]aminocarbonyl}cyclopent-2-en-1-yl]methyl acetate and [(1S,5R)-5-{[(1R)-1-phenylethyl]aminocarbonyl}cyclopent-2-en-1-yl]methyl acetate reacted with m-chloroperoxybenzoic acid to give the corresponding stereoisomeric alpha- and beta-epoxy derivatives, which were identified on the basis of their spectral parameters.

  DOI：

  10.1134/s1070428010040135

文献信息

• Simple synthetic protocol for the preparation of enantiomeric 3-oxabicyclo[3.3.0]oct-6-en-2-ones
  作者：Airat M. Gimazetdinov、Nikolay S. Vostrikov、Mansur S. Miftakhov

  DOI：10.1016/j.tetasy.2008.04.001

  日期：2008.5

  Diastereomeric amides produced via the decomposition of easily available (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one by treatment with (+)- or (-)-alpha-methylbenzylamines were transformed into bicyclic lactam-aminals, which can easily be separated using the column chromatography on SiO2. The latter products lead to enantiomeric 3-oxabicyclo[3.3.0]oct-6-en-2-ones after the removal of the chiral auxiliary. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.
• Synthesis of enantiomeric cyclosarcomycins
  作者：Airat M. Gimazetdinov、Tat’yana V. Gimazetdinova、Mansur S. Miftakhov

  DOI：10.1016/j.mencom.2010.01.006

  日期：2010.1

  Based on chiral cyclopentene blocks 2 and 3, enantiomeric cyclosarcomycins 4 and 5 were obtained and characterised.
• Epoxy derivatives of {(5-[(1-Phenylethyl)aminocarbonyl]-cyclopent-2-en-1-yl}methyl acetates
  作者：A. M. Gimazetdinov、M. S. Miftakhov

  DOI：10.1134/s1070428010040135

  日期：2010.4

  Diastereoisomeric [(1R,5S)-5-[(1R)-1-phenylethyl]aminocarbonyl}cyclopent-2-en-1-yl]methyl acetate and [(1S,5R)-5-[(1R)-1-phenylethyl]aminocarbonyl}cyclopent-2-en-1-yl]methyl acetate reacted with m-chloroperoxybenzoic acid to give the corresponding stereoisomeric alpha- and beta-epoxy derivatives, which were identified on the basis of their spectral parameters.
• Sarkomycin A methyl esters and functionalized cyclopentane blocks for brefeldin A
  作者：A. M. Gimazetdinov、G. V. Ishmurzina、M. S. Miftakhov

  DOI：10.1134/s1070428012010022

  日期：2012.1

  Sarkomycin A methyl esters and functionalized cyclopentane blocks for brefeldin A were synthesized starting from diastereoisomeric (1R,2S)- and (1S,2R)-2-hydroxymethyl-N-[(1R)-1-phenylethyl]cyclopent-3-ene-1-carboxamides.