[1-(4-bromophenyl)pyrrolidin-3-yl]methanol | 848317-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: [1-(4-bromophenyl)pyrrolidin-3-yl]methanol
• 英文别名: [N-(4-bromophenyl)pyrrolidin-3-yl]methanol；(1-(4-Bromophenyl)pyrrolidin-3-yl)methanol
• CAS: 848317-67-9
• 化学式: C₁₁H₁₄BrNO
• 分子量: 256.142
• InChiKey: FIYQYASDCRIEFC-UHFFFAOYSA-N

物化性质

• 沸点：
  374.5±17.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1-(4-bromophenyl)pyrrolidin-3-yl]methanol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 8.0h， 以64%的产率得到1-(4-溴苯基)-3-甲酰基吡咯
  参考文献：
  名称：

  Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl-formylpyrroles and 1,3-diaryl-formylpyrroles

  摘要：

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4-I-2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and intermediates in the synthesis of several bioactive compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.058
• 作为产物：
  描述：

  衣康酸 在 sodium tetrahydroborate 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 [1-(4-bromophenyl)pyrrolidin-3-yl]methanol
  参考文献：
  名称：

  Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl-formylpyrroles and 1,3-diaryl-formylpyrroles

  摘要：

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4-I-2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and intermediates in the synthesis of several bioactive compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.058

文献信息

• Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a facile entry to N-aryl-formylpyrroles
  作者：Pranab Haldar、Joyram Guin、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2004.12.107

  日期：2005.2

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-arylpyri-olidine-2/3-yl)-methanols in good yields at room temperature using sodium borohydride-iodine. Controlled oxidation and aromatisation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles. (C) 2004 Elsevier Ltd. All rights reserved.
• Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl-formylpyrroles and 1,3-diaryl-formylpyrroles
  作者：Pranab Haldar、Gopa Barman、Jayanta K. Ray

  DOI：10.1016/j.tet.2007.01.058

  日期：2007.4

  A simple methodology for the conversion of substituted N-aryl-gamma-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-gamma-lactam 2/3-carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4-I-2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and intermediates in the synthesis of several bioactive compounds. (c) 2007 Elsevier Ltd. All rights reserved.