2-((2-benzothiazolyl)oxy)ethyl 2-(ethoxycarbonyl)ethenyl sulfoxide | 1236046-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-((2-benzothiazolyl)oxy)ethyl 2-(ethoxycarbonyl)ethenyl sulfoxide
• 英文别名: ethyl (E)-3-[2-(1,3-benzothiazol-2-yloxy)ethylsulfinyl]prop-2-enoate
• CAS: 1236046-99-3
• 化学式: C₁₄H₁₅NO₄S₂
• 分子量: 325.409
• InChiKey: NUPPIKHXAQOMAR-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丙炔酸乙酯 、 2-benzothiazolyl 2-hydroxyethyl sulfoxide 反应 72.0h， 以59%的产率得到2-((2-benzothiazolyl)oxy)ethyl 2-(ethoxycarbonyl)ethenyl sulfoxide
  参考文献：
  名称：

  Thermal Reactions of β-Hydroxysulfides Bearing Benzothiazole: Sulfenic Acid Trapping via a Spiro Intermediate

  摘要：

  Benzothiazolyl 2-hydroxyethyl sulfoxide (1a) was found to afford bis[2-(2-oxobenzotiazolyl)-ethyl] disulfide (2a) in the presence of DBU at rt. 2a was formed by the condensation of corresponding sulfenic acid intermediate. Thermolyses of 1a in the presence of ethyl propiolate at 60-140 degrees C were carried out to succeed to trap sulfenic acid 6a as an intermediate. Trapping of 2-benzothiazolyloxyenthanesulfenic acid (6a) revealed that the thermal reaction proceeded via a five-membered spiro intermediate 5a.

  DOI：

  10.1080/10426501003773480

文献信息

• Thermal Reactions of β-Hydroxysulfides Bearing Benzothiazole: Sulfenic Acid Trapping via a Spiro Intermediate
  作者：Nobuhiko Yamada、Takanori Koyasu、Mayumi Sonami、Michiko Aoi、Shintaro Tashiro、Md. Chanmiya Sheikh、Yusuke Ishida、Wataru Kawashima、Toshiaki Yoshimura、Hiroyuki Morita

  DOI：10.1080/10426501003773480

  日期：2010.5.27

  Benzothiazolyl 2-hydroxyethyl sulfoxide (1a) was found to afford bis[2-(2-oxobenzotiazolyl)-ethyl] disulfide (2a) in the presence of DBU at rt. 2a was formed by the condensation of corresponding sulfenic acid intermediate. Thermolyses of 1a in the presence of ethyl propiolate at 60-140 degrees C were carried out to succeed to trap sulfenic acid 6a as an intermediate. Trapping of 2-benzothiazolyloxyenthanesulfenic acid (6a) revealed that the thermal reaction proceeded via a five-membered spiro intermediate 5a.