S-dodecyl propynethioate | 1286783-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: S-dodecyl propynethioate
• 英文别名: S-dodecyl prop-2-ynethioate
• CAS: 1286783-50-3
• 化学式: C₁₅H₂₆OS
• 分子量: 254.437
• InChiKey: CDBPBUTVZWQOIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5H-5-methyl-2-(4-trifluoromethylphenyl)oxazol-4-one 、 S-dodecyl propynethioate 在 (S)-bis[3,5-bis(trifluoromethyl)phenyl](3,3-dimethyl-1,5,7-triazabicyclo-[4.3.0]-non-5-ene-8-yl)methanol 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 dodecyl (E)-3-[5H-5-methyl-4-oxo-2-(4-trifluoromethylphenyl)oxazol-5-yl]propenethioate 、 dodecyl (Z)-3-[(R)-5H-5-methyl-4-oxo-2-(4-trifluoromethylphenyl)oxazol-5-yl]propenethioate 、 dodecyl (E)-3-[5H-5-methyl-4-oxo-2-(4-trifluoromethylphenyl)oxazol-5-yl]propenethioate
  参考文献：
  名称：

  HighlyZ-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines

  摘要：

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.

  DOI：

  10.1021/ja200283n
• 作为产物：
  描述：

  在 sodium tetraborate decahydrate 、 水 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以1.12 g的产率得到S-dodecyl propynethioate
  参考文献：
  名称：

  HighlyZ-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines

  摘要：

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.

  DOI：

  10.1021/ja200283n