5-ethenyl-1-(4-bromo-2-formylphenyl)-2-pyrrolidinone | 393562-47-5

• 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: 5-ethenyl-1-(4-bromo-2-formylphenyl)-2-pyrrolidinone
• 英文别名: 5-Bromo-2-(2-ethenyl-5-oxopyrrolidin-1-yl)benzaldehyde
• CAS: 393562-47-5
• 化学式: C₁₃H₁₂BrNO₂
• 分子量: 294.148
• InChiKey: LXSSFJDOLUQCNV-UHFFFAOYSA-N

物化性质

• 沸点：
  481.7±45.0 °C(Predicted)
• 密度：
  1.554±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-ethenyl-1-(4-bromo-2-formylphenyl)-2-pyrrolidinone 在 锂硼氢 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 207.0h， 生成
  参考文献：
  名称：

  Total Synthesis of (±)-Martinellic Acid

  摘要：

  [GRAPHICS]A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH4 and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degreesC as key steps,

  DOI：

  10.1021/ol016884o
• 作为产物：
  描述：

  2-氨基-5-溴苯甲醇 在 manganese(IV) oxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 5-ethenyl-1-(4-bromo-2-formylphenyl)-2-pyrrolidinone
  参考文献：
  名称：

  Total Synthesis of (±)-Martinellic Acid

  摘要：

  [GRAPHICS]A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH4 and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degreesC as key steps,

  DOI：

  10.1021/ol016884o

文献信息

• Total Synthesis of (±)-Martinellic Acid
  作者：Barry B. Snider、Yong Ahn、Sean M. O'Hare

  DOI：10.1021/ol016884o

  日期：2001.12.1

  [GRAPHICS]A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH4 and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degreesC as key steps,