1,3-bis(phenylsulfonyl)-4-phenyl-3,4,6,7-tetrahydro-11bH-benzoquinoline | 133167-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1,3-bis(phenylsulfonyl)-4-phenyl-3,4,6,7-tetrahydro-11bH-benzoquinoline
• 英文别名: (3S,4R)-1,3-bis(benzenesulfonyl)-4-phenyl-4,6,7,11b-tetrahydro-3H-benzo[a]quinolizine
• CAS: 133167-31-4
• 化学式: C₃₁H₂₇NO₄S₂
• 分子量: 541.692
• InChiKey: SFWNYRBCTAMVDC-OZLLHVCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  71.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  sodium benzenesulfonate 在 哌啶 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 28.58h， 生成 1,3-bis(phenylsulfonyl)-4-phenyl-3,4,6,7-tetrahydro-11bH-benzoquinoline
  参考文献：
  名称：

  Formation of polysubstituted 1,2,5,6-tetrahydropyridines from the 4+2 cycloaddition reaction of bis(phenylsulfonyl)butadienes with aryl imines

  摘要：

  The reaction of 2,3-bis(phenylsulfonyl)-1,3-butadiene with aryl imines affords N-alkyl-3,5-bis(phenylsulfonyl)-1,2,5,6-tetrahydropyridines in high yield. The formation of the rearranged cycloadducts proceeds by a mechanism that involves addition of benzenesulfinate anion onto the terminal pi-bond of the activated diene. The resulting carbanion undergoes proton transfer followed by aryl sulfinate ejection to give 1,3-bis(phenylsulfonyl)-1,3-butadiene as a transient intermediate. This reactive diene undergoes a rapid 4 + 2 cycloaddition followed by a subsequent hydrogen 1,3-shift. Support for the proposed mechanism is provided by the observation that a mixed cycloadduct is obtained from the reaction of a 1:1 mixture of 2,3-bis(phenylsulfonyl)- and 2,3-bis[(o-nitrophenyl)sulfonyl]butadiene with N-benzylidenemethylamine. An additional piece of supporting data for the proposed mechanism is the much shorter reaction time necessary for the reaction to go to completion when a small amount of sodium benzenesulfinate is added to the reaction mixture. 1,3-Bis(phenylsulfonyl)butadiene was independently synthesized by two different routes. This diene was found to rapidly react with a variety of imines to give the same cycloadducts as those derived from the 2,3-isomer. The reaction of several 4-substituted 1,3-bis(phenylsulfonyl)butadienes with aryl imines was found to give related 4 + 2 cycloadducts.

  DOI：

  10.1021/jo00008a026

文献信息

• PADWA, ALBERT;GAREAU, YVES;HARRISON, BRIAN;NORMAN, BRYAN H., J. ORG. CHEM., 56,(1991) N, C. 2713-2720
  作者：PADWA, ALBERT、GAREAU, YVES、HARRISON, BRIAN、NORMAN, BRYAN H.

  DOI：——

  日期：——