环氧乙烷基甲基 十八烷基氨基甲酸酯 | 94135-55-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 环氧乙烷基甲基 十八烷基氨基甲酸酯
• 中文别名: 环氧乙烷基甲基十八烷基氨基甲酸酯；L-γ-谷氨酰-S-[(1E)-1,2,3,4,4-五氯丁-1,3-二烯-1-基]-L-半胱氨酰甘氨酸
• 英文名称: O-(Octadecylcarbamoyl)glycidol
• 英文别名: Oxiranylmethyl octadecylcarbamate；oxiran-2-ylmethyl N-octadecylcarbamate
• CAS: 94135-55-4
• 化学式: C₂₂H₄₃NO₃
• 分子量: 369.588
• InChiKey: INEYIRFSQAWYPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  26
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基膦酸二乙酯 、 环氧乙烷基甲基 十八烷基氨基甲酸酯 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以94%的产率得到Diethyl 3-hydroxy-4-(octadecylcarbamoyl)butanephosphonate
  参考文献：
  名称：

  A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides

  摘要：

  A practical and facile method for the preparation of hydroxy phosphonate esters is described. Regiospecific ring opening of monosubstituted epoxides by phosphorus and carbon nucleophiles, derived from diethyl phosphite and methanephosphonates, in the presence of BF3.OEt2 furnishes the corresponding beta- and gamma-hydroxy phosphonates, respectively. Ketals, bromides, sulfonate esters, and carbamates (compounds 12, 13, 15, 16, and 18) are stable under the reaction conditions, but benzoate esters(14) behave differently. While they survive phosphite nucleophilicity, they are cleaved by phosphonates. Several chirons (2, 28a, 30b, and 31) for the synthesis of phosphonate isosteres of nucleotides and phospholipids are also described.

  DOI：

  10.1021/jo00073a043
• 作为产物：
  描述：

  异氰酸十八酯 、 缩水甘油 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到环氧乙烷基甲基 十八烷基氨基甲酸酯
  参考文献：
  名称：

  A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides

  摘要：

  A practical and facile method for the preparation of hydroxy phosphonate esters is described. Regiospecific ring opening of monosubstituted epoxides by phosphorus and carbon nucleophiles, derived from diethyl phosphite and methanephosphonates, in the presence of BF3.OEt2 furnishes the corresponding beta- and gamma-hydroxy phosphonates, respectively. Ketals, bromides, sulfonate esters, and carbamates (compounds 12, 13, 15, 16, and 18) are stable under the reaction conditions, but benzoate esters(14) behave differently. While they survive phosphite nucleophilicity, they are cleaved by phosphonates. Several chirons (2, 28a, 30b, and 31) for the synthesis of phosphonate isosteres of nucleotides and phospholipids are also described.

  DOI：

  10.1021/jo00073a043

文献信息

• A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides
  作者：Zhengong Li、Saibaba Racha、Li Dan、Hussein El-Subbagh、Elie Abushanab

  DOI：10.1021/jo00073a043

  日期：1993.10

  A practical and facile method for the preparation of hydroxy phosphonate esters is described. Regiospecific ring opening of monosubstituted epoxides by phosphorus and carbon nucleophiles, derived from diethyl phosphite and methanephosphonates, in the presence of BF3.OEt2 furnishes the corresponding beta- and gamma-hydroxy phosphonates, respectively. Ketals, bromides, sulfonate esters, and carbamates (compounds 12, 13, 15, 16, and 18) are stable under the reaction conditions, but benzoate esters(14) behave differently. While they survive phosphite nucleophilicity, they are cleaved by phosphonates. Several chirons (2, 28a, 30b, and 31) for the synthesis of phosphonate isosteres of nucleotides and phospholipids are also described.