(R)-ethyl 1,5,2-dithiazepane-3-carboxylate 1,1-dioxide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-ethyl 1,5,2-dithiazepane-3-carboxylate 1,1-dioxide
• 英文别名: ethyl (3R)-1,1-dioxo-1,5,2-dithiazepane-3-carboxylate
• 化学式: C₇H₁₃NO₄S₂
• 分子量: 239.317
• InChiKey: KRTVQKROIYSURY-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 1,5,2-dithiazepane-3-carboxylate 1,1-dioxide 在 2-羟基吡啶 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成 (R)-2-benzyl-N-octyl-1,5,2-dithiazepane-3-carboxamide 1,1-dioxide
  参考文献：
  名称：

  Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol

  摘要：

  A novel one-pot sulfonylation/intramolecular thia-Michael protocol is reported for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. Sulfonylation between cysteine ethyl ester/cysteamine and 2-chloroethanesulfonyl chloride, followed by in situ intramolecular thia-Michael addition, was achieved and afforded the titled 1,5,2-dithiazepine-1,1-dioxide scaffolds. Diversification was demonstrated for future library synthesis.

  DOI：

  10.3987/com-12-s(n)121
• 作为产物：
  描述：

  2-氯乙烷磺酰氯 、 L-半胱氨酸乙酯盐酸盐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到(R)-ethyl 1,5,2-dithiazepane-3-carboxylate 1,1-dioxide
  参考文献：
  名称：

  Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol

  摘要：

  A novel one-pot sulfonylation/intramolecular thia-Michael protocol is reported for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. Sulfonylation between cysteine ethyl ester/cysteamine and 2-chloroethanesulfonyl chloride, followed by in situ intramolecular thia-Michael addition, was achieved and afforded the titled 1,5,2-dithiazepine-1,1-dioxide scaffolds. Diversification was demonstrated for future library synthesis.

  DOI：

  10.3987/com-12-s(n)121

文献信息

• SYNTHESIS OF A LIBRARY OF 1,5,2-DITHIAZAPINE 1,1-DIOXIDES. PART 2: ROUTES TO BICYCLIC SULTAMS
  作者：Paul R. Hanson、Qin Zang、Salim Javed、Aihua Zhou、Chirs A. Knudtson、Danse Bi、Fatima Z. Basha

  DOI：10.3987/com-12-s(n)122

  日期：——

  The synthesis of a library of bicyclic sultams incorporating the 1,5,2-dithiazepine 1,1-dioxide moiety is reported. Following scaffold synthesis via a one-pot sulfonylation/intramolecular thia-Michael protocol, several additional cyclization strategies have been realized enabling access to new bicyclic sultams.

  报道了包含 1,5,2-二硫氮杂 1,1-二氧化物部分的双环 sultam 库的合成。在通过一锅磺酰化/分子内硫-迈克尔方案合成支架后，已经实现了几种额外的环化策略，从而能够获得新的双环 sultam。
• Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol
  作者：Paul R. Hanson、Qin Zang、Aihua Zhou、Salim Javed、Pradip K. Maity、Chirs A. Knudtson、Danse Bi、Jared J. Hastings、Fatima Z. Basha

  DOI：10.3987/com-12-s(n)121

  日期：——

  A novel one-pot sulfonylation/intramolecular thia-Michael protocol is reported for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. Sulfonylation between cysteine ethyl ester/cysteamine and 2-chloroethanesulfonyl chloride, followed by in situ intramolecular thia-Michael addition, was achieved and afforded the titled 1,5,2-dithiazepine-1,1-dioxide scaffolds. Diversification was demonstrated for future library synthesis.