2-methylthio-3-phenyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine

• 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-methylthio-3-phenyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine
• 英文别名: 2-methylsulfanyl-3-phenyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine
• 化学式: C₁₆H₁₉NS
• 分子量: 257.4
• InChiKey: DIKQWKQENJBZJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环己亚胺 、 2-tert-butylthio-3-phenylcyclopropenethione 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以25%的产率得到2-methylthio-3-phenyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine
  参考文献：
  名称：

  One-Pot Synthesis of N-Heterocyclic Compounds from Cyclopropenethione Derivatives

  摘要：

  The one-pot reaction of 2-tert-butylthio-3-phenylcyclopropenethione (1a) and its 3-(2-thienyl) derivative (1b) with lithium pyrrolidinide at -70 degrees C, followed by methylation with methyl iodide, gives 6-methylthio-5-phenyl-2,3-dihydro-1H-pyrrolizine (2a) and its 5-(2-thienyl) derivative (2b), respectively. The reaction of 2-tert-butylthio-3-(pyrrolidin-1-yl)cyclopropenethione (1c) with phenyllithium gives also 2a in a high yield under similar conditions, and the reactions of la with N-lithium salts of 3-pyrroline, hexamethyleneimine, indoline, and carbazole, piperidine-potassium tert-butoxide mixture, and phenyllithium give 6-methylthio-5-phenyl-3H-pyrrolizine (3), 2-methylthio-3-phenyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2a]azepine (5), 6-tert-butylthio-5-methylthio-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline (8), 4-tert-butylthio-5-methylthio-6-phenyl-4H-pyrido[3,2, 1-jk]carbazole (7), 2-methylthio-3-phenyl-5,6,7,8-tetrahydroindolizine (4), and 1-tert-butylthio-2-methylthio-3-phenylindene (9), respectively. The structures of 2a and 3 were determined by X-ray analyses of their tricarbonylchromium complexes.

  DOI：

  10.1021/jo991640r

文献信息

• One-Pot Synthesis of <i>N</i>-Heterocyclic Compounds from Cyclopropenethione Derivatives
  作者：Noboru Matsumura、Yoshio Yagyu、Masamichi Ito、Tomohiro Adachi、Kazuhiko Mizuno

  DOI：10.1021/jo991640r

  日期：2000.6.1

  The one-pot reaction of 2-tert-butylthio-3-phenylcyclopropenethione (1a) and its 3-(2-thienyl) derivative (1b) with lithium pyrrolidinide at -70 degrees C, followed by methylation with methyl iodide, gives 6-methylthio-5-phenyl-2,3-dihydro-1H-pyrrolizine (2a) and its 5-(2-thienyl) derivative (2b), respectively. The reaction of 2-tert-butylthio-3-(pyrrolidin-1-yl)cyclopropenethione (1c) with phenyllithium gives also 2a in a high yield under similar conditions, and the reactions of la with N-lithium salts of 3-pyrroline, hexamethyleneimine, indoline, and carbazole, piperidine-potassium tert-butoxide mixture, and phenyllithium give 6-methylthio-5-phenyl-3H-pyrrolizine (3), 2-methylthio-3-phenyl-6,7,8,9-tetrahydro-5H-pyrrolo[1,2a]azepine (5), 6-tert-butylthio-5-methylthio-4-phenyl-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline (8), 4-tert-butylthio-5-methylthio-6-phenyl-4H-pyrido[3,2, 1-jk]carbazole (7), 2-methylthio-3-phenyl-5,6,7,8-tetrahydroindolizine (4), and 1-tert-butylthio-2-methylthio-3-phenylindene (9), respectively. The structures of 2a and 3 were determined by X-ray analyses of their tricarbonylchromium complexes.