(R)-ethyl 3-hydroxy-7-tetradecynoate | 1025737-47-6

• 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: (R)-ethyl 3-hydroxy-7-tetradecynoate
• 英文别名: ethyl (3R)-3-hydroxytetradec-7-ynoate
• CAS: 1025737-47-6
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: XQVTZZYBYDASDM-OAHLLOKOSA-N

物化性质

• 沸点：
  381.6±32.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 3-hydroxy-7-tetradecynoate 在 borohydride exchange resin 、 nickel(II) acetate tetrahydrate 、 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到(3R,7Z)-ethyl 3-hydroxy-7-tetradecanoate
  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
• 作为产物：
  描述：

  1-碘-3-癸炔 、 (S)-2-噁丙环乙酸乙酯 在 叔丁基锂 、 copper(l) iodide 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 为溶剂， 以24%的产率得到(R)-ethyl 3-hydroxy-7-tetradecynoate
  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

文献信息

• Synthesis and Stereochemistry-Activity Relationship of <i>small</i> Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium <i>Rhizobium leguminosarum</i>
  作者：Arata Yajima、Anton A. N. van Brussel、Jan Schripsema、Tomoo Nukada、Goro Yabuta

  DOI：10.1021/ol8005198

  日期：2008.5.1

  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.