cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester | 151415-02-0

• 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: cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester
• 英文别名: methyl (2R,4R)-4-[(Z)-7-methoxy-7-oxohept-1-enyl]-2-phenyl-1,3-thiazolidine-3-carboxylate
• CAS: 151415-02-0
• 化学式: C₁₉H₂₅NO₄S
• 分子量: 363.478
• InChiKey: HNXAJBGWZZEMTR-FPNRTYGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester 在 氢溴酸 、 溴 作用下， 以 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 20.33h， 生成 5-<4(S)-Amino-3(R)-bromotetrahydrothiophen-2(R)-yl>pentanoic acid methyl ester
  参考文献：
  名称：

  Novel Enantioselective Syntheses of (+)-Biotin

  摘要：

  Two conceptually attractive enantioselective syntheses of(+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide. The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of(+)-biotin 16a and 17a. The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b. Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.

  DOI：

  10.1021/jo00107a009
• 作为产物：
  描述：

  6-溴己酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 17.5h， 生成 cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel Enantioselective Syntheses of (+)-Biotin

  摘要：

  Two conceptually attractive enantioselective syntheses of(+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide. The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of(+)-biotin 16a and 17a. The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b. Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.

  DOI：

  10.1021/jo00107a009

文献信息

• A novel enantioselective synthesis of (+)-biotin
  作者：Frederik D. Deroose、Pierre J. De Clercq

  DOI：10.1016/s0040-4039(00)79354-3

  日期：1993.7

  enantioselective 14-step synthesis of (+)-biotin from L-cysteine is reported based upon an intramolecular 1,3-dipolar cycloaddition sequence involving (i) elimination of bromide 8 to the endocyclic thioenol ether 9, (ii) thermolysis of the ene carbamoyl azide 9 to the exocyclic thioenol ether 10. Both the synthesis of 8 and the final transformation of 10 into (+)-biotin are based upon literature precedents

  基于分子内的1,3-偶极环加成序列，报道了从L-半胱氨酸在概念上简单的对映选择性的14步合成（+）-生物素，涉及（i）将溴化物8消除至环内硫烯醇醚9，（ii）热解烯氨基甲酰基叠氮化物9与环硫代烯醇醚10的反应。8的合成和10最终转化为（+）-生物素的过程均基于文献先例。