2,3,4,5-Tetrahydro-6H-1,6-benzothiazocine-6-carboxaldehyde | 76801-01-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3,4,5-Tetrahydro-6H-1,6-benzothiazocine-6-carboxaldehyde
• 英文别名: 1,6-benzothiazocine；2,3,4,5-Tetrahydro-1,6-benzothiazocine-6-carbaldehyde
• CAS: 76801-01-9
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: SQWAEUVKFYUFTP-UHFFFAOYSA-N

物化性质

• 沸点：
  361.9±12.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4'-Bromo-1'-butyl)benzothiazolium iodide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以52%的产率得到2,3,4,5-Tetrahydro-6H-1,6-benzothiazocine-6-carboxaldehyde
  参考文献：
  名称：

  A convenient quaternization/rearrangement procedure for conversion of thiazoles to medium- and large-sized N,S-heterocycles

  摘要：

  A straightforward, two-step sequence capable of converting simple thiazoles into different sets of ring-expanded N,S-heterocycles of various sizes has been developed. The initial quaternizations of the heterocyclic moieties conducted with alpha,omega-dihaloalkanes (chain lengths from 2 to 8) in a 1:5 stoichiometry, afford the monoquaternary intermediates in isolated yields ranging from 16-71% (benzothiazole series, 9) to 17-93% (thiazole series, 10), respectively. In the subsequent OH-induced rearrangement, an expeditious ring-opening/ring-closure event incorporates the previously attached alkyl side chain in the newly formed hetero ring. Here the yields of benzannelated products 11 lie in the interval from 39 to 82%, while the monocyclic counterparts 12 fall within 11 to 59%, which in an overall perspective makes this methodology preparatively significant for an array of new compounds up to (at least) 12-membered ring sizes.

  DOI：

  10.1021/jo00113a044

文献信息

• A novel base-induced ring expansion of quaternized heterocycles
  作者：Hans-Jürgen Federsel、Jan Bergman

  DOI：10.1016/s0040-4039(00)93167-8

  日期：1980.1

  The synthesis of some 6-, 7- and 8-membered heterocycles through a base induced ring expansion of quaternized thiazolium, oxazolium and selenazolium salts is described.

  描述了通过季铵化的噻唑鎓盐，恶唑鎓盐和硒氮鎓盐的碱诱导的环膨胀来合成一些6-，7-和8-元杂环。