(S)-t-butyl 3-hydroxy-7-thiotetradecynoate | 1025737-58-9

• 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: (S)-t-butyl 3-hydroxy-7-thiotetradecynoate
• CAS: 1025737-58-9
• 化学式: C₁₈H₃₂O₂S
• 分子量: 312.517
• InChiKey: JUSNNCXXEFSYIW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1-tert-butylsulfanyl-vinyloxy)trimethylsilane 、 5-dodecynal 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol 作用下， 以 乙醚 为溶剂， 生成 (R)-t-butyl 3-hydroxy-7-thiotetradecynoate 、 (S)-t-butyl 3-hydroxy-7-thiotetradecynoate
  参考文献：
  名称：

  Synthesis and Stereochemistry-Activity Relationship of small Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium Rhizobium leguminosarum

  摘要：

  The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.

  DOI：

  10.1021/ol8005198