1-(2-methyl-2-propenyl)pyrrole | 355114-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-methyl-2-propenyl)pyrrole
• 英文别名: 2-methyl-3-(pyrrol-1-yl)prop-1-ene；N-(beta-methallyl)pyrrole；1-(2-methylprop-2-enyl)pyrrole
• CAS: 355114-74-8
• 化学式: C₈H₁₁N
• 分子量: 121.182
• InChiKey: QLZTYGUDGZPNMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-(2-methyl-2-propenyl)pyrrole 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 33.83h， 生成 perfluorophenyl 2-(1-(2-methylallyl)-1H-pyrrol-2-yl)acetate
  参考文献：
  名称：

  通过异硫脲/钯协同催化对映选择性合成 α-烷基化吡咯。

  摘要：

  在此，我们描述了吡咯乙酸酯的直接对映选择性路易斯碱/Pd 催化的 α-烯丙基化。这提供了高度对映体富集的产物的高分离产率，并且对于两种反应伙伴表现出广泛的反应范围。该产品可以很容易地以一种指向目标定向合成的潜在应用的方式进行阐述。

  DOI：

  10.1039/c8ob02600a
• 作为产物：
  描述：

  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63%的产率得到1-(2-methyl-2-propenyl)pyrrole
  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。
• Fe-Catalyzed Hydroallylation of Unactivated Alkenes with Vinyl Cyclopropanes
  作者：Biplab Mondal、Subhadeep Hazra、Ayan Chatterjee、Manveer Patel、Jaideep Saha

  DOI：10.1021/acs.orglett.3c02105

  日期：2023.8.4
• 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.
• An enantioselective synthesis of α-alkylated pyrroles <i>via</i> cooperative isothiourea/palladium catalysis
  作者：W. Rush Scaggs、Toya D. Scaggs、Thomas N. Snaddon

  DOI：10.1039/c8ob02600a

  日期：——

  Herein we describe the direct enantioselective Lewis base/Pd catalysed α-allylation of pyrrole acetic acid esters. This provides high isolated yields of highly enantioenriched products and exhibits broad reaction scope with respect to both reaction partners. The products can be readily elaborated in a manner which points towards potential applications in target directed synthesis.

  在此，我们描述了吡咯乙酸酯的直接对映选择性路易斯碱/Pd 催化的 α-烯丙基化。这提供了高度对映体富集的产物的高分离产率，并且对于两种反应伙伴表现出广泛的反应范围。该产品可以很容易地以一种指向目标定向合成的潜在应用的方式进行阐述。