(Z)-N-(6-hydroxyhex-3-enyl)-4-methylbenzenesulfonamide | 1218780-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-N-(6-hydroxyhex-3-enyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(Z)-6-hydroxyhex-3-enyl]-4-methylbenzenesulfonamide
• CAS: 1218780-91-6
• 化学式: C₁₃H₁₉NO₃S
• 分子量: 269.365
• InChiKey: AZZYWLYHGKQUGZ-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-N-(6-hydroxyhex-3-enyl)-4-methylbenzenesulfonamide 、 (±)-4-氯苯乙烯环氧化物 在 对甲苯磺酸 、 碳酸氢钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以67%的产率得到(3aSR,4SR,7aSR)-4-(4-chlorobenzyl)-octahydro-1-tosylpyrano[4,3-b]pyrrole
  参考文献：
  名称：

  Versatile Intramolecular Aza-Prins and Prins Cyclization of Aryl Epoxides: A Facile Synthesis of Diaza-, Oxa-aza-, and Dioxa-bicycles

  摘要：

  Aryl epoxides undergo coupling smoothly with (E)-hex-3-ene-1,6-ditosylamide in the presence of 10 mol % p-TSA in 1,2-dichloroethane at 75 degrees C to produce the corresponding 1,5-ditosyl-octahydro-1H-pyrrolidino-[3,2-c]pyridines in good yields with high trans-selectivity, whereas the coupling of (Z)-hex-3-ene-1,6-ditosylamide gave cis-fused octahydro-1H-pyrrolidino[3,2-c]pyridines predominantly. The use of readily available p-TSA makes this method simple, convenient, and practical.

  DOI：

  10.1021/jo902683p

文献信息

• Sc(OTf)3-catalyzed intramolecular aza-Prins cyclization for the synthesis of heterobicycles
  作者：B.V. Subba Reddy、Prashant Borkar、P. Pawan Chakravarthy、J.S. Yadav、Rene Gree

  DOI：10.1016/j.tetlet.2010.04.093

  日期：2010.6

  aldehydes in the presence of 10 mol % Sc(OTf)3 gave the corresponding trans- and cis-fused 1,5-ditosyl-octahydro-1H-pyrrolo[3,2-c]pyridines, respectively, in good yields via intramolecular aza-Prins cyclization, whereas the coupling of (E)- and (Z)-N-(6-hydroxyhex-3-enyl)-4-methylbenzenesulfonamide afforded the corresponding trans- and cis-fused octahydro-1-tosylpyrano[4,3-b]pyrroles derivatives, respectively

  的耦合（ë） -和（Ž）中的10摩尔％的存在-己-3-烯-1,6- ditosylamide与各种醛钪（OTF）3，得到相应的反式-和顺式-融合1,5- -二甲苯基-八氢-1 H-吡咯并[3,2- c ]吡啶分别通过分子内氮杂-Prins环化获得高收率，而（E）-和（Z）-N-（6-羟基己基-丁-3-烯基）-4-甲基苯磺酰胺，得到相应的反式-和顺-融合八氢-1- tosylpyrano [4,3- b]吡咯衍生物，分别通过分子内Prins环化。
• Versatile Intramolecular Aza-Prins and Prins Cyclization of Aryl Epoxides: A Facile Synthesis of Diaza-, Oxa-aza-, and Dioxa-bicycles
  作者：Jillu S. Yadav、Prashant Borkar、P. Pawan Chakravarthy、Basi V. Subba Reddy、Akella V. S. Sarma、Shaik Jeelani Basha、Balasubramanian Sridhar、René Grée

  DOI：10.1021/jo902683p

  日期：2010.3.19

  Aryl epoxides undergo coupling smoothly with (E)-hex-3-ene-1,6-ditosylamide in the presence of 10 mol % p-TSA in 1,2-dichloroethane at 75 degrees C to produce the corresponding 1,5-ditosyl-octahydro-1H-pyrrolidino-[3,2-c]pyridines in good yields with high trans-selectivity, whereas the coupling of (Z)-hex-3-ene-1,6-ditosylamide gave cis-fused octahydro-1H-pyrrolidino[3,2-c]pyridines predominantly. The use of readily available p-TSA makes this method simple, convenient, and practical.