ethyl (2S,3R)-4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate | 106501-27-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2S,3R)-4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate
• CAS: 106501-27-3；106520-16-5
• 化学式: C₁₂H₂₀O₃S₂
• 分子量: 276.421
• InChiKey: CHVIGAODUNWANY-SKDRFNHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3R)-4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate 在 盐酸 、 potassium tert-butylate 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.25h， 生成 2-Benzyloxy-4-(3-mercapto-propylsulfanylcarbonyl)-2,3-dimethyl-butyric acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester
  参考文献：
  名称：

  Use of Ketene Dithioacetal as a Latent Carboxylic Acid in the Macrolactonization Applicable to the Synthesis of Dilactonic Pyrrolizidine Alkaloids

  摘要：

  Acid 5a (or 5b) bearing the ketene dithioacetal moiety functioned as an equivalent of a dicarboxylic acid. Use of the ketene dithioacetal in the formation of 11-membered dilactones is demonstrated. Compound 5a (or 5b) was converted to an acid imidazolide which reacted regioselectively with retronecine at the allylic position. Mild acidic hydrolysis of the ketene dithioacetal moiety led to a thioester, which underwent macrocyclization with the secondary hydroxyl group mediated by silver(I) trifluoroacetate to give derivatives of the pyrrolizidine alkaloids.

  DOI：

  10.1021/jo951363y
• 作为产物：
  描述：

  丙酮酸乙酯 、 2-((E)-2-propen-1-yl)-[1,3]dithiane 在 正丁基锂 、 zinc(II) chloride 作用下， 生成 ethyl (2S,3R)-4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate 、
  参考文献：
  名称：

  Stereoselective reaction of dithio-substituted crotylmetal with .alpha.-oxy carbonyl compounds

  摘要：

  DOI：

  10.1021/jo00390a036

文献信息

• Dichotomous regiochemistry of aldehyde and ketone in the reaction with dithio-substituted crotyllithium
  作者：Jim Min Fang、Bor Cherng Hong、Li Fan Liao

  DOI：10.1021/jo00381a026

  日期：1987.3
• Use of Ketene Dithioacetal as a Latent Carboxylic Acid in the Macrolactonization Applicable to the Synthesis of Dilactonic Pyrrolizidine Alkaloids
  作者：Wen-Chih Chou、Jim-Min Fang

  DOI：10.1021/jo951363y

  日期：1996.1.1

  Acid 5a (or 5b) bearing the ketene dithioacetal moiety functioned as an equivalent of a dicarboxylic acid. Use of the ketene dithioacetal in the formation of 11-membered dilactones is demonstrated. Compound 5a (or 5b) was converted to an acid imidazolide which reacted regioselectively with retronecine at the allylic position. Mild acidic hydrolysis of the ketene dithioacetal moiety led to a thioester, which underwent macrocyclization with the secondary hydroxyl group mediated by silver(I) trifluoroacetate to give derivatives of the pyrrolizidine alkaloids.
• Stereoselective reaction of dithio-substituted crotylmetal with .alpha.-oxy carbonyl compounds
  作者：Jim Min Fang、Bor Cherng Hong

  DOI：10.1021/jo00390a036

  日期：1987.7