(2R)-1-(1H-吡咯-1-基)-2-丙醇 | 158151-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: (2R)-1-(1H-吡咯-1-基)-2-丙醇
• 英文名称: (2R)-1-(1H-pyrrol-1-yl)-2-propanol
• 英文别名: (R)-1-(1H-Pyrrol-1-yl)propan-2-ol；(2R)-1-pyrrol-1-ylpropan-2-ol
• CAS: 158151-20-3
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: UJMFUOHZAQFYCK-SSDOTTSWSA-N

物化性质

• 沸点：
  215.2±23.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (2R)-1-(1H-吡咯-1-基)-2-丙醇 在 4-二甲氨基吡啶 、 三溴化硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 [2-[1-[(2R)-2-hydroxypropyl]pyrrol-2-yl]-2-oxoethyl] acetate
  参考文献：
  名称：

  A concise synthesis of two pyrroles of marine origin

  摘要：

  2-Ethanolamine and (2R)-2-aminopropanol were converted into their N-pyrrole derivatives, 14 and 15, by reaction with 2,5-dimethoxytetrahydrofuran. The acetoxyacetyl derivatives of 14 and 15 were prepared and submitted to BBr3-promoted rearrangement. Acetylation of the resulting (2-acetoxyacetyl)pyrrol-1-yl-2-ethanol and 2-propanol furnished the corresponding acetates.

  DOI：

  10.1016/s0040-4039(00)73409-5
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 (R)-(-)-1-氨基-2-丙醇 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以83%的产率得到(2R)-1-(1H-吡咯-1-基)-2-丙醇
  参考文献：
  名称：

  The synthesis of chiral 1-(1H-pyrrole) derivatives

  摘要：

  Enantiomerically pure primary amines possessing an epimerizable center, such as alpha-amino acids and their ester hydrochlorides, undergo condensation with tetrahydro-2,5-dimethoxyfuran 2 in acetic acid or acetic acid containing sodium acetate at 80 degrees C for 30 min. to give the corresponding 1-(1H-pyrrolyl) derivatives with partial racemization (9-18%). By replacing the solvent with a stirred mixture of aqueous acetic acid and 1,2-dichloroethane in the case of the acids and with water-1,2-dichloroethane for the ester hydrochlorides, repetition of the previous experiment gives the corresponding pyrroles in high yield and with complete retention of configuration, beta-Aminoalcohols are also efficiently converted to their 1-(1H-pyrrolyl) derivatives in a stirred, warm mixture of aqueous acetic acid and 1,2-dichloroethane. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00111-5

文献信息

• The synthesis of chiral 1-(1H-pyrrole) derivatives
  作者：Charles W. Jefford、Fabienne de Villedon de Naide、Krzysztof Sienkiewicz

  DOI：10.1016/0957-4166(96)00111-5

  日期：1996.4

  Enantiomerically pure primary amines possessing an epimerizable center, such as alpha-amino acids and their ester hydrochlorides, undergo condensation with tetrahydro-2,5-dimethoxyfuran 2 in acetic acid or acetic acid containing sodium acetate at 80 degrees C for 30 min. to give the corresponding 1-(1H-pyrrolyl) derivatives with partial racemization (9-18%). By replacing the solvent with a stirred mixture of aqueous acetic acid and 1,2-dichloroethane in the case of the acids and with water-1,2-dichloroethane for the ester hydrochlorides, repetition of the previous experiment gives the corresponding pyrroles in high yield and with complete retention of configuration, beta-Aminoalcohols are also efficiently converted to their 1-(1H-pyrrolyl) derivatives in a stirred, warm mixture of aqueous acetic acid and 1,2-dichloroethane. Copyright (C) 1996 Elsevier Science Ltd
• A concise synthesis of two pyrroles of marine origin
  作者：Charles W. Jefford、Krzysztof Sienkiewicz、Steven R. Thornton

  DOI：10.1016/s0040-4039(00)73409-5

  日期：1994.8

  2-Ethanolamine and (2R)-2-aminopropanol were converted into their N-pyrrole derivatives, 14 and 15, by reaction with 2,5-dimethoxytetrahydrofuran. The acetoxyacetyl derivatives of 14 and 15 were prepared and submitted to BBr3-promoted rearrangement. Acetylation of the resulting (2-acetoxyacetyl)pyrrol-1-yl-2-ethanol and 2-propanol furnished the corresponding acetates.