methyl 3-chloroacetyl-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate | 478239-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: methyl 3-chloroacetyl-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
• 英文别名: 4H-Thieno[3,2-b]pyrrole-5-carboxylic acid, 3-(2-chloroacetyl)-2-methyl-, methyl ester；methyl 3-(2-chloroacetyl)-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
• CAS: 478239-07-5
• 化学式: C₁₁H₁₀ClNO₃S
• 分子量: 271.724
• InChiKey: QVRHQLAPFJTJBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-chloroacetyl-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate 在 吡啶 、 sodium sulfide 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 6.5h， 生成 3,4-bis-(2-methyl-5-methoxycarbonyl-4H-thieno[3,2-b]pyrrol-3-yl)-2,5-dihydrothiophene
  参考文献：
  名称：

  Synthesis of Photochromic 1,2-Dihetarylethene Using Regioselective Acylation of Thienopyrroles

  摘要：

  [GRAPHICS]The influence of catalysts, acid chlorides, and solvents in the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. Conditions for the regioselective acylation processes were found. Thienopyrrole-based photochrome was synthesized for the first time.

  DOI：

  10.1021/ol026705i
• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 methyl 3-chloroacetyl-2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  Synthesis of Photochromic 1,2-Dihetarylethene Using Regioselective Acylation of Thienopyrroles

  摘要：

  [GRAPHICS]The influence of catalysts, acid chlorides, and solvents in the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. Conditions for the regioselective acylation processes were found. Thienopyrrole-based photochrome was synthesized for the first time.

  DOI：

  10.1021/ol026705i

文献信息

• Synthesis of Photochromic 1,2-Dihetarylethene Using Regioselective Acylation of Thienopyrroles
  作者：Michael M. Krayushkin、Vladimir N. Yarovenko、Stanislav L. Semenov、Igor V. Zavarzin、Anatoliy V. Ignatenko、Andrey Yu. Martynkin、Boris M. Uzhinov

  DOI：10.1021/ol026705i

  日期：2002.10.1

  [GRAPHICS]The influence of catalysts, acid chlorides, and solvents in the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. Conditions for the regioselective acylation processes were found. Thienopyrrole-based photochrome was synthesized for the first time.
• ——
  作者：V. N. Yarovenko

  DOI：10.1023/a:1023435605723

  日期：——

  The influence of catalysts, acid chlorides, and solvents on the acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate was studied. The use of AlCl3 allows the regioselective introduction of the acyl group into position 3 to be performed, whereas the acyl group is regioselectively introduced into position 6 of thienopyrrole when SnCl4 is used.
• Fotochromic Dihetarylethenes: XIX. Synthesis of 1,2-Dihetarylethenes with 2,5-Dihydrothiophene Bridge from Thieno[3,2-b]pyrroles
  作者：M. M. Krayushkin、V. N. Yarovenko、S. L. Semenov、I. V. Zavarzin、A. Yu. Martynkin、B. M. Uzhinov

  DOI：10.1023/b:rujo.0000013143.33985.26

  日期：2003.11

  Reductive cyclization by McMurry method was performed with diketosulfide obtained by treating with Na2S of compound prepared by regioselective acylation of methyl 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate with chloroacetyl chloride. As a result was synthesized a photochromic 1,2-dihetaryl-ethene where the fuzed rings are connected by a 2,5-dihydrothiophene ring. The oxidation of the latter provides 2,5-dihydrothiophene-1,1-dioxide bridge.