5-oxo-4,5,6,7,8,9-hexahydro-thieno[3,2-b]azocine-3-carboxylic acid methyl ester | 59851-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-oxo-4,5,6,7,8,9-hexahydro-thieno[3,2-b]azocine-3-carboxylic acid methyl ester
• 英文别名: 5-oxo-4,5,6,7,8,9-hexahydro-thieno[3,2-b]azocine-3-carboxylic acid methyl ester；3-Amino-4-carbomethoxy-2-thiophenvaleriansaeurelactam
• CAS: 59851-12-6
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: FOGFSARYFHZKEL-UHFFFAOYSA-N

物化性质

• 沸点：
  448.3±45.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-oxo-4,5,6,7,8,9-hexahydro-thieno[3,2-b]azocine-3-carboxylic acid methyl ester 在 肼 作用下， 反应 2.0h， 生成 D-生物素
  参考文献：
  名称：

  从芳香族前体立体定向合成生物素。

  摘要：

  AbstractThe total synthesis of the important natural product biotin 1 from the readily available keto diester 3 is described. This approach features the stereospecific hydrogenation of the thiophene intermediate 19 as the key synthetic step.The required differentiation of the diacid functionality of compound 7 is achieved by selective lactam formation with the terminal acid to yield the 8‐membered lactam 8. A modified Curtius reaction then affords the rearranged diurethane 18 through a series of acyl transfers. Finally, a novel conversion of the 3, 4‐diurethane moiety to the imidazolidone portion of biotin is utilized to complete the synthesis.

  DOI：

  10.1002/hlca.19760590405
• 作为产物：
  描述：

  5-(3-amino-4-methoxycarbonyl-thiophen-2-yl)-pentanoic acid 以 xylene 为溶剂， 生成 5-oxo-4,5,6,7,8,9-hexahydro-thieno[3,2-b]azocine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  从芳香族前体立体定向合成生物素。

  摘要：

  AbstractThe total synthesis of the important natural product biotin 1 from the readily available keto diester 3 is described. This approach features the stereospecific hydrogenation of the thiophene intermediate 19 as the key synthetic step.The required differentiation of the diacid functionality of compound 7 is achieved by selective lactam formation with the terminal acid to yield the 8‐membered lactam 8. A modified Curtius reaction then affords the rearranged diurethane 18 through a series of acyl transfers. Finally, a novel conversion of the 3, 4‐diurethane moiety to the imidazolidone portion of biotin is utilized to complete the synthesis.

  DOI：

  10.1002/hlca.19760590405