(1R,5S,6R,16R)-5,6-dimethyl-6-phenylmethoxy-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione | 174319-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,5S,6R,16R)-5,6-dimethyl-6-phenylmethoxy-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
• CAS: 174319-52-9
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: UKOPPRQIGRESIX-GDUHTRTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,5S,6R,16R)-5,6-dimethyl-6-phenylmethoxy-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione 在 palladium on activated charcoal 氢气 作用下， 生成 (4aR,8S,9R,12bR)-9-Benzyloxy-8,9-dimethyl-decahydro-5,11-dioxa-2a-aza-cycloundeca[cd]pentalene-6,10-dione
  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：

  ethyl (2S,3R)-4-(1,3-dithian-2-ylidene)-2-hydroxy-2,3-dimethylbutanoate 在 potassium tert-butylate 、 水 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.67h， 生成 (1R,5S,6R,16R)-5,6-dimethyl-6-phenylmethoxy-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
  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