methyl 1-(2-chloroethyl)-1H-indole-3-carboxylate | 250355-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 1-(2-chloroethyl)-1H-indole-3-carboxylate
• 英文别名: Methyl 1-(2-chloroethyl)indole-3-carboxylate
• CAS: 250355-37-4
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: GGTQIXQBQAPMRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1-(2-chloroethyl)-1H-indole-3-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 乙腈 、 苯 为溶剂， 100.0 ℃ 、8.11 MPa 条件下， 反应 27.0h， 生成 1-ethyl-1H-indole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole

  摘要：

  The AIBN-induced radical reaction of 1-(2-iodoethyl)indoles and pyrroles with Bu3SnH under 80 atm of CO was examined. Carbon monoxide was efficiently trapped by an alkyl radical to form an acyl radical which underwent intramolecular addition to the aromatic system to produce bicyclic aromatic ketones after in situ oxidation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01346-5
• 作为产物：
  描述：

  吲哚-3-甲酸甲酯 、 1,2-二氯乙烷 在 sodium hydroxide 、 四丁基碘化铵 作用下， 以94%的产率得到methyl 1-(2-chloroethyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole

  摘要：

  The AIBN-induced radical reaction of 1-(2-iodoethyl)indoles and pyrroles with Bu3SnH under 80 atm of CO was examined. Carbon monoxide was efficiently trapped by an alkyl radical to form an acyl radical which underwent intramolecular addition to the aromatic system to produce bicyclic aromatic ketones after in situ oxidation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01346-5

文献信息

• Iridium(III) Photocatalysis: A Visible-Light-Induced Dearomatizative Tandem [4+2] Cyclization to Furnish Benzindolizidines
  作者：Sandra Mühmel、Dirk Alpers、Frank Hoffmann、Malte Brasholz

  DOI：10.1002/chem.201502572

  日期：2015.8.24

  tandem [4+2] cyclization between N‐(2‐iodoethyl)indoles and a variety of alkenes leads to tri‐ and tetracyclic benzindolizidines with high diastereoselectivity and yield. The intermolecular annulation reaction is performed under visible‐light irradiation and employs [Ir(ppy)3] or [Ir(dtbbpy)(ppy)2] PF6 as photocatalysts, in combination with tertiary amines as electron and hydrogen atom donors.

  N-（2-碘乙基）吲哚与各种烯烃之间的光催化脱芳香串联双环[4 + 2]环化反应会生成具有高非对映选择性和收率的三环和四环苯并吲哚并咪唑。分子间的环化反应在可见光照射下进行，并使用[Ir（ppy）3 ]或[Ir（dtbbpy）（ppy）2 ] PF 6作为光催化剂，并与叔胺结合作为电子和氢原子供体。