2-methyl-3-(2-ethylpyrrol-1-yl)prop-1-ene | 355114-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-methyl-3-(2-ethylpyrrol-1-yl)prop-1-ene
• 英文别名: 2-ethyl-1-(2-methyl-2-propenyl)pyrrole；1H-Pyrrole, 2-ethyl-1-(2-methyl-2-propenyl)-；2-ethyl-1-(2-methylprop-2-enyl)pyrrole
• CAS: 355114-75-9
• 化学式: C₁₀H₁₅N
• mdl: MFCD18810032
• 分子量: 149.236
• InChiKey: IWOMJSGKOCEMNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  213.0±19.0 °C(Predicted)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2-methyl-3-(2-ethylpyrrol-1-yl)prop-1-ene 在 dodecacarbonyltetrarhodium(0) 、 氢气 作用下， 以 甲苯 为溶剂， 100.0 ℃ 、10.13 MPa 条件下， 以72%的产率得到3-ethyl-6-methyl-5,6-dihydroindonizine
  参考文献：
  名称：

  An original approach to 5,6-dihydroindolizines from 1-allylpyrroles by a tandem hydroformylation/cyclization/dehydration sequence

  摘要：

  6-Methyl-5,6-dihydroindolizine and 3- or 2-ethyl derivatives were obtained via a one-pot hydroformylation/cyclization/dehydration sequence starting from 1-(2-methyl-2-propenyl)pyrroles. 7-Phenyl-5,6-dihydroindolizine and 5-methyl-5,6-dihydroindolizine were similarly synthesized. An easily occurring electrophilic aromatic substitution by the carbon atom of the carbonyl group on the cl-position of the pyrrole ring with the formation of the six-membered ring is the key-step of the process. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00625-6
• 作为产物：
  描述：

  2-乙基吡咯 、 alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以68%的产率得到2-methyl-3-(2-ethylpyrrol-1-yl)prop-1-ene
  参考文献：
  名称：

  An original approach to 5,6-dihydroindolizines from 1-allylpyrroles by a tandem hydroformylation/cyclization/dehydration sequence

  摘要：

  6-Methyl-5,6-dihydroindolizine and 3- or 2-ethyl derivatives were obtained via a one-pot hydroformylation/cyclization/dehydration sequence starting from 1-(2-methyl-2-propenyl)pyrroles. 7-Phenyl-5,6-dihydroindolizine and 5-methyl-5,6-dihydroindolizine were similarly synthesized. An easily occurring electrophilic aromatic substitution by the carbon atom of the carbonyl group on the cl-position of the pyrrole ring with the formation of the six-membered ring is the key-step of the process. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00625-6

文献信息

• Synthesis of 5,6,7,8-tetrahydroindolizines<i>via</i>a domino-type transformation based on the rhodium catalyzed hydroformylation of<i>N</i>-(β-methallyl)pyrroles
  作者：Silvia Rocchiccioli、Giuditta Guazzelli、Raffaello Lazzaroni、Roberta Settambolo

  DOI：10.1002/jhet.5570440234

  日期：2007.3

  Variously substituted 5,6,7,8-tetrahydroindolizines can be easily synthesized via a domino reactions sequence under rhodium catalyzed hydroformylation of N-(β-methallyl)pyrroles. The later are readily prepared from properly functionalized pyrroles via phase-transfer N-allylation in the presence of 18-crown-6 and potassium tert-butoxide.

  在铑催化的N-（β-甲代烯丙基）吡咯的加氢甲酰化反应下，可以通过多米诺反应序列容易地合成各种取代的5,6,7,8-四氢吲哚并吲哚。后者可以容易地由适当官能化的吡咯在18-冠-6和叔丁醇钾存在下通过相转移N-烯丙基化制备。
• An original approach to 5,6-dihydroindolizines from 1-allylpyrroles by a tandem hydroformylation/cyclization/dehydration sequence
  作者：Roberta Settambolo、Aldo Caiazzo、Raffaello Lazzaroni

  DOI：10.1016/s0040-4039(01)00625-6

  日期：2001.6

  6-Methyl-5,6-dihydroindolizine and 3- or 2-ethyl derivatives were obtained via a one-pot hydroformylation/cyclization/dehydration sequence starting from 1-(2-methyl-2-propenyl)pyrroles. 7-Phenyl-5,6-dihydroindolizine and 5-methyl-5,6-dihydroindolizine were similarly synthesized. An easily occurring electrophilic aromatic substitution by the carbon atom of the carbonyl group on the cl-position of the pyrrole ring with the formation of the six-membered ring is the key-step of the process. (C) 2001 Elsevier Science Ltd. All rights reserved.