tert-butyl N-[2-(3,3-dimethoxy-2-oxobutyl)sulfanylethyl]carbamate | 207795-30-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[2-(3,3-dimethoxy-2-oxobutyl)sulfanylethyl]carbamate
• CAS: 207795-30-0
• 化学式: C₁₃H₂₅NO₅S
• 分子量: 307.411
• InChiKey: JZSJUWUTZUGIIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(3,3-dimethoxy-2-oxobutyl)sulfanylethyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到1-(3,4-二氢-2H-1,4-噻嗪-5-基)乙酮
  参考文献：
  名称：

  Novel Syntheses of 5-Acetyl-2,3-dihydro-1,4-thiazine, a Very Intense Roasty, Popcornlike Odorant

  摘要：

  Two new synthetic pathways toward the new Maillard flavor compound 5-acetyl-2,3-dihydro-1,4-thiazine are disclosed. 1-Bromo-3,3-dimethoxy-2-butanone and N-protected 2 -mercaptoethylamine are the key components in both synthetic routes. The first approach involves a one-step synthesis via nucleophilic substitution, followed by cyclization and hydrolysis. The second route entails a nucleophilic substitution, followed by TFA-deprotection of the primary amino function, which led to a spontaneous intramolecular transimination and hydrolysis of the acetal moiety to afford the desired flavor compound in very good yield.

  DOI：

  10.1021/jf971004z
• 作为产物：
  描述：

  N-(3,3,-dimethoxy-2-butylidene)isopropylamine 在 N-溴代丁二酰亚胺(NBS) 、 草酸 、 三乙胺 作用下， 以 四氯化碳 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 tert-butyl N-[2-(3,3-dimethoxy-2-oxobutyl)sulfanylethyl]carbamate
  参考文献：
  名称：

  Novel Syntheses of 5-Acetyl-2,3-dihydro-1,4-thiazine, a Very Intense Roasty, Popcornlike Odorant

  摘要：

  Two new synthetic pathways toward the new Maillard flavor compound 5-acetyl-2,3-dihydro-1,4-thiazine are disclosed. 1-Bromo-3,3-dimethoxy-2-butanone and N-protected 2 -mercaptoethylamine are the key components in both synthetic routes. The first approach involves a one-step synthesis via nucleophilic substitution, followed by cyclization and hydrolysis. The second route entails a nucleophilic substitution, followed by TFA-deprotection of the primary amino function, which led to a spontaneous intramolecular transimination and hydrolysis of the acetal moiety to afford the desired flavor compound in very good yield.

  DOI：

  10.1021/jf971004z

文献信息

• Novel Syntheses of 5-Acetyl-2,3-dihydro-1,4-thiazine, a Very Intense Roasty, Popcornlike Odorant
  作者：Norbert G. De Kimpe、Maria Teresa Rocchetti

  DOI：10.1021/jf971004z

  日期：1998.6.1

  Two new synthetic pathways toward the new Maillard flavor compound 5-acetyl-2,3-dihydro-1,4-thiazine are disclosed. 1-Bromo-3,3-dimethoxy-2-butanone and N-protected 2 -mercaptoethylamine are the key components in both synthetic routes. The first approach involves a one-step synthesis via nucleophilic substitution, followed by cyclization and hydrolysis. The second route entails a nucleophilic substitution, followed by TFA-deprotection of the primary amino function, which led to a spontaneous intramolecular transimination and hydrolysis of the acetal moiety to afford the desired flavor compound in very good yield.