9-(toluene-4-sulfonyl)-1,3,4,6,7,8-hexahydro-2H-quinolizine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: 9-(toluene-4-sulfonyl)-1,3,4,6,7,8-hexahydro-2H-quinolizine
• 英文别名: 9-(4-methylphenyl)sulfonyl-2,3,4,6,7,8-hexahydro-1H-quinolizine
• 化学式: C₁₆H₂₁NO₂S
• 分子量: 291.414
• InChiKey: VHBWHPNMAIUABN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-(toluene-4-sulfonyl)-hex-5-yn-1-ol 在 4 A molecular sieve 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 91.0h， 生成 9-(toluene-4-sulfonyl)-1,3,4,6,7,8-hexahydro-2H-quinolizine
  参考文献：
  名称：

  A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues

  摘要：

  The omega-iodo-alpha,beta-alkynoates and their ketone, sulfone or phosphonate analogues react with delta-chloropropylamines in MeCN assisted with K2CO3 to undergo a sequential S(N)2/Michael addition/S(N)2/S(N)2 reaction process, giving polysubstituted indolizidines or quinolizidines in good to excellent yields. This sequential reaction process is also compatible with three other substituted alpha,beta-alkynoates, affording quinolizidine analogues in moderate to good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.068

文献信息

• An Efficient Sequential Reaction Process to Polysubstituted Indolizidines and Quinolizidines and Its Application to the Total Synthesis of Indolizidine 223A
  作者：Wei Zhu、Dapeng Dong、Xiaotao Pu、Dawei Ma

  DOI：10.1021/ol047476y

  日期：2005.2.1

  The reaction of iodides 1 with delta-chloropropylamines 5 in MeCN assisted with K2CO3 undergoes a sequential S(N)2/Michael addition/SN2/SN2 reaction process to give polysubstituted indolizidines and quinolizidines. Using this method, indolizidine 223A is synthesized from 2-ethyl-2-hexenoic acid in 12 linear steps and 14.5% overall yield. [Reaction: see text]

  碘化物1与δ-氯丙胺5在MeCN中辅以K2CO3的反应按顺序进行S（N）2 / Michael加成/ SN2 / SN2反应，得到多取代的吲哚并咪唑和喹喔啉。使用该方法，由吲哚并咪唑223A由2-乙基-2-己酸以12个线性步骤合成，并且总产率为14.5％。[反应：请参阅文字]