1-(2-iodo-4,5-dimethylbenzyl)pyrrole-2-carboxylic acid methoxy methyl amide | 524024-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-iodo-4,5-dimethylbenzyl)pyrrole-2-carboxylic acid methoxy methyl amide
• 英文别名: 1-(2-iodo-4,5-dimethylbenzyl)-N-methyl-N-methoxypyrrol-2-carboxamide；1-[(2-iodo-4,5-dimethylphenyl)methyl]-N-methoxy-N-methylpyrrole-2-carboxamide
• CAS: 524024-81-5
• 化学式: C₁₆H₁₉IN₂O₂
• 分子量: 398.244
• InChiKey: AXVFQDKEJUJWDF-UHFFFAOYSA-N

物化性质

• 熔点：
  76-79 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  496.2±40.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-iodo-4,5-dimethylbenzyl)pyrrole-2-carboxylic acid methoxy methyl amide 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 3.0h， 以80%的产率得到7,8-dimethyl-5H-pyrrolo[1,2-b]isoquinolin-10-one
  参考文献：
  名称：

  Parham-Type Cycliacylation with Weinreb Amides. Application to the Synthesis of Fused Indolizinone Systems

  摘要：

  [GRAPHIC]Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.

  DOI：

  10.1021/ol034194+
• 作为产物：
  描述：

  吡咯-2-羧酸 在 氢氧化钾 、 氯化亚砜 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 19.0h， 生成 1-(2-iodo-4,5-dimethylbenzyl)pyrrole-2-carboxylic acid methoxy methyl amide
  参考文献：
  名称：

  Parham-Type Cycliacylation with Weinreb Amides. Application to the Synthesis of Fused Indolizinone Systems

  摘要：

  [GRAPHIC]Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.

  DOI：

  10.1021/ol034194+

文献信息

• An efficient entry to pyrrolo[1,2-b]isoquinolines and related systems through Parham cyclisation
  作者：Javier Ruiz、Ainhoa Ardeo、Roberto Ignacio、Nuria Sotomayor、Esther Lete

  DOI：10.1016/j.tet.2004.10.105

  日期：2005.3

  Aryllithiums generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b]isoquinolines, in high yields. The best results were obtained when Weinreb or morpholine amides were used as internal electrophiles. The procedure has been extended to the preparation of seven and eight membered rings, opening a route to benzazepine and benzazocine skeletons. (c) 2004 Elsevier Ltd. All rights reserved.
• Parham-Type Cycliacylation with Weinreb Amides. Application to the Synthesis of Fused Indolizinone Systems
  作者：Javier Ruiz、Nuria Sotomayor、Esther Lete

  DOI：10.1021/ol034194+

  日期：2003.4.1

  [GRAPHIC]Weinreb amides behave as efficient internal electrophiles in Parham-type cycliacylation reactions. Thus, aryl- and heteroaryllithiums generated by lithium-halogen exchange undergo intramolecular cyclization to give fused indolizinone systems as pyrrolo[1,2-b]isoquinolines, thieno[2,3-f]indolizinones, and pyrrolo[1,2-b]acridinones in high yields.