cis-8(R)-<(tert-Butoxycarbonyl)amino>-9-mercaptonon-6-enoic acid | 157020-36-5

• 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-8(R)-<(tert-Butoxycarbonyl)amino>-9-mercaptonon-6-enoic acid
• 英文别名: (Z,8R)-8-[(2-methylpropan-2-yl)oxycarbonylamino]-9-sulfanylnon-6-enoic acid
• CAS: 157020-36-5
• 化学式: C₁₄H₂₅NO₄S
• 分子量: 303.423
• InChiKey: OHYOLLMFFHJDKP-BPOWMSRESA-N

物化性质

• 沸点：
  452.3±45.0 °C(predicted)
• 密度：
  1.104±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  76.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-8(R)-<(tert-Butoxycarbonyl)amino>-9-mercaptonon-6-enoic acid 在 吡啶 、 盐酸 、 sodium azide 、 buffer: citric acid pH 4 、 硫酸 、 sodium cyanoborohydride 、 碳酸氢钠 、 magnesium sulfate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二氯磷酸苯酯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 45.67h， 生成 <3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-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：

  cis-4(R)-(6-Carboxyhex-1-enyl)-2(R)-phenylthiazolidine-3-carboxylic acid tert-butyl ester 在 氨 、 sodium 作用下， 反应 2.0h， 以95%的产率得到cis-8(R)-<(tert-Butoxycarbonyl)amino>-9-mercaptonon-6-enoic acid
  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

• Novel Enantioselective Syntheses of (+)-Biotin
  作者：Frederik D. Deroose、Pierre J. De Clercq

  DOI：10.1021/jo00107a009

  日期：1995.1

  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.