(+)-(1R,2S)-2-(2-Methyl-1H-pyrrol-1-yl)-1-phenylpropan-1-ol | 189231-38-7

• 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-(2-Methyl-1H-pyrrol-1-yl)-1-phenylpropan-1-ol
• 英文别名: (1R,2S)-2-(2-methylpyrrol-1-yl)-1-phenylpropan-1-ol
• CAS: 189231-38-7
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: JEGIFBJPLLXIIA-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-(1R,2S)-2-(2-Methyl-1H-pyrrol-1-yl)-1-phenylpropan-1-ol 在 氧气 、 焦磷酸硫胺素 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到1-[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-5-methylene-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  The synthesis of chiral 5-methylene pyrrol-2(5H)-ones via photooxygenation of homochiral 2-methylpyrrole derivatives

  摘要：

  Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amines, amino alcohols and amino acid esters. The photooxygenation of these pyrrole derivatives in the presence of a photosensitiser furnishes the corresponding alpha,beta,gamma,delta-unsaturated gamma-lactams as the major products in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00140-4
• 作为产物：
  描述：

  去甲麻黄碱 、 5-chloro-3-penten-2-one 在 三乙胺 作用下， 反应 4.0h， 以78%的产率得到(+)-(1R,2S)-2-(2-Methyl-1H-pyrrol-1-yl)-1-phenylpropan-1-ol
  参考文献：
  名称：

  Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-methylpyrrole derivatives

  摘要：

  5-Chloro-3-penten-2-one reacts with the amino group of homochiral amines, amino alcohols, amino acid esters to form corresponding 2-pyrrole derivatives in good yield and without racemization. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00035-9

文献信息

• Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives
  作者：Ayhan S. Demir、Idris M. Akhmedov、Özge Şeşenoglu、Onur Alptürk、Sinem Apaydın、Zuhal Gerçek、Nezire Ibrahimzade

  DOI：10.1039/b008317h

  日期：——

  The conversion of the amino group of chiral amines, amino alcohols, amino acids and their esters into chiral 2-substituted pyrrole derivatives with various halogeno enones is described. The conversion works in good yield and without racemization. The synthesis of 2-phenylpyrrole derivatives was possible with amino alcohols but not with amino acids or their esters.

  介绍了将手性胺、氨基醇、氨基酸及其酯的氨基基团转化为具有各种卤代烯酮的手性2-取代吡咯衍生物的方法。该转化在良好产率下进行，且不会发生消旋化。氨基醇能够合成2-苯基吡咯衍生物，而氨基酸或其酯则不能。
• Synthesis and photooxygenation of homochiral 2-methylpyrrole derivatives of chiral amino alcohols: simple, selective access to chiral bicyclic lactams
  作者：Feray Aydogan、Ayhan S. Demir

  DOI：10.1016/j.tetasy.2003.11.011

  日期：2004.1

  Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amino alcohols and 5-chloro-3-pentene-2-one. The photooxygenation of these compounds in the presence of a photosynthesizer furnishes the pyrrolooxazolone structures in high diastereoselectivities. In all of the examples, trans-isomers are formed as the major products. (C) 2003 Elsevier Ltd. All rights reserved.