(3R,7Z)-ethyl 3-hydroxy-7-tetradecanoate | 1025737-49-8

• 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: (3R,7Z)-ethyl 3-hydroxy-7-tetradecanoate
• 英文别名: (R,Z)-ethyl 3-hydroxytetradec-7-enoate；ethyl (Z,3R)-3-hydroxytetradec-7-enoate
• CAS: 1025737-49-8
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: TXICTKHNWKOOGI-FJVVXJACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  13
• 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：

  (3R,7Z)-ethyl 3-hydroxy-7-tetradecanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以87%的产率得到(3R,7Z)-3-hydroxy-7-tetradecenoic acid
  参考文献：
  名称：

  （2对映选择性合成小号，3' - [R，7' ž - ）ñ - （3'-羟基-7'- tetradecenoyl）高丝氨酸内酯

  摘要：

  （2的简明对映选择性全合成小号，3' - [R，7' ž - ）ñ - （3'-羟基-7'- tetradecenoyl）高丝氨酸内酯进行说明。该方案的主要特点是催化不对称氢化和亚胺反应中前苯酚-锌催化的重氮加成反应是手性的成因。而且，在合成中建立了灵活性，以使用催化量的对映体富集的C 2对称配体来产生对映体富集的类似物。

  DOI：

  10.1016/j.tetlet.2010.09.138
• 作为产物：
  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

文献信息

• Enantioselective synthesis of (2S,3′R,7′Z)-N-(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone
  作者：Gullapalli Kumaraswamy、Neerasa Jayaprakash

  DOI：10.1016/j.tetlet.2010.09.138

  日期：2010.12

  A concise enantioselective total synthesis of (2S,3′R,7′Z)-N-(3′-hydroxy-7′-tetradecenoyl)-homoserine lactone is described. Key feature of this protocol is a catalytic asymmetric hydrogenation and a prophenol–zinc-catalyzed diazo addition to imine reaction as genesis of chirality. Moreover, flexibility is built in the synthesis to generate enantioenriched analogs using catalytic amount of enantioenriched

  （2的简明对映选择性全合成小号，3' - [R，7' ž - ）ñ - （3'-羟基-7'- tetradecenoyl）高丝氨酸内酯进行说明。该方案的主要特点是催化不对称氢化和亚胺反应中前苯酚-锌催化的重氮加成反应是手性的成因。而且，在合成中建立了灵活性，以使用催化量的对映体富集的C 2对称配体来产生对映体富集的类似物。
• 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.