2,3-dihydro-4H-benzo[b][1,4]thiazine-4-carbaldehyde | 76800-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2,3-dihydro-4H-benzo[b][1,4]thiazine-4-carbaldehyde
• 英文别名: 2,3-Dihydro-4H-1,4-benzothiazine-4-carboxaldehyde；2H-benzo[b][1,4]thiazine-4(3H)-carbaldehyde；2H-benzo[b][1,4]thiazin-4(3H)-formaldehyde；4-Formyl-2,3-dihydro-4H-1,4-benzothiazine；1,4-benzothiazine；2,3-Dihydro-1,4-benzothiazine-4-carbaldehyde
• CAS: 76800-99-2
• 化学式: C₉H₉NOS
• 分子量: 179.243
• InChiKey: RUCJIEDADQGMPI-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  335.2±22.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-4H-benzo[b][1,4]thiazine-4-carbaldehyde 在 lithium diisopropyl amide 、 碘甲烷 作用下， 反应 1.75h， 生成 N-(trifluoroacetyl)-N-<2-(methylthio)phenyl>ethenamine
  参考文献：
  名称：

  Eliminative ring fission of 4-acyl-2,3-dihydro-4H-1,4-benzothiazines

  摘要：

  DOI：

  10.1021/jo00170a042
• 作为产物：
  描述：

  3-(2-Chloroethyl)-1,3-benzothiazol-3-ium 在 base 作用下， 生成 2,3-dihydro-4H-benzo[b][1,4]thiazine-4-carbaldehyde
  参考文献：
  名称：

  一种新型的碱诱导的季铵化杂环的环扩展

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)93167-8

文献信息

• 一种以溴代二氟乙酸乙酯为甲酰化试剂制备 出的N-芳基甲酰胺
  申请人：温州大学

  公开号：CN108774147B

  公开（公告）日：2021-01-08

  本发明公开了一种以溴代二氟乙酸乙酯为甲酰化试剂制备出的N‑芳基甲酰胺，以N‑烷基芳胺为原料，溴代二氟乙酸乙酯为甲酰化试剂，铜做催化剂，通过加入不同的配体、碱等，在反应的溶剂中，于100‑120℃下，搅拌反应10‑14小时；反应结束，对反应液进行过滤，获得滤液；对滤液进行浓缩并用旋转蒸发仪除去溶剂获得剩余物，通过硅胶柱对剩余物进行层析，并经洗脱液进行淋洗，按实际梯度收集流出液；合并含有产物的流出液，对合并后的流出液进行浓缩去溶剂，最后经真空干燥得到目标产物。本发明具有原料简单易得，制备工艺简单、污染少、耗能低、产率高的优点。
• Copper-Catalyzed <i>N</i>-Formylation of Amines through Tandem Amination/Hydrolysis/Decarboxylation Reaction of Ethyl Bromodifluoroacetate
  作者：Xiao-Fang Li、Xing-Guo Zhang、Fan Chen、Xiao-Hong Zhang

  DOI：10.1021/acs.joc.8b01555

  日期：2018.10.19

  Ethyl bromodifluoroacetate (BrCF2COOEt) was first used as the N-formylating reagent in the copper-catalyzed N-formylation of amines. A range of primary, secondary, cyclic arylamines, and aliphatic amines underwent the N-formylation smoothly to furnish the N-formamides in moderate-to-excellent yields.

  溴代二氟乙酸乙酯（BrCF 2 COOEt烷基）首次用作Ñ在铜催化-formylating试剂Ñ胺-formylation。伯，仲，环状芳基胺，和脂族胺的范围接受所述Ñ -formylation顺利，得到的Ñ -formamides在中度至优异的产率。
• A convenient quaternization/rearrangement procedure for conversion of thiazoles to medium- and large-sized N,S-heterocycles
  作者：Hans-Juergen Federsel、Gunilla Glasare、Christina Hoegstroem、Jan Wiestl、Barbara Zinko、Christina Oedman

  DOI：10.1021/jo00113a044

  日期：1995.4

  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.
• An efficient method for the N-formylation of amines under catalyst- and additive-free conditions
  作者：Zhuo-Wei Xu、Wen-Yi Xu、Xiao-Jun Pei、Fei Tang、Yi-Si Feng

  DOI：10.1016/j.tetlet.2019.03.071

  日期：2019.5

  A simple catalyst- and additive-free method for the N-formylation of amines has been developed. The advantages of this protocol include a wide range of functional group tolerance, high efficiency and a lack of required extra promoters under mild conditions. This convenient strategy will provide a facile synthesis towards N-formamide natural products and pharmaceutical derivatives. A mechanism that involves difluorocarbene is proposed for this reaction. (C) 2019 Elsevier Ltd. All rights reserved.
• FEDERSEL H.-J.; BERGMAN J., TETRAHEDRON LETT., 1980 21, NO 25, 2429-2432
  作者：FEDERSEL H.-J.、 BERGMAN J.

  DOI：——

  日期：——

表征谱图