2-[(2S,3R,7R)-3,7-dimethyltridecan-2-yl]oxycarbonylbenzoic acid | 924650-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(2S,3R,7R)-3,7-dimethyltridecan-2-yl]oxycarbonylbenzoic acid
• CAS: 924650-93-1
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: SZIQOECSULMDFR-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2S,3R,7R)-3,7-dimethyltridecan-2-yl]oxycarbonylbenzoic acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以99%的产率得到(2S,3R,7R)-3,7-dimethyl-2-tridecanol
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005
• 作为产物：
  描述：

  在 盐酸 作用下， 以 苯 为溶剂， 生成 2-[(2S,3R,7R)-3,7-dimethyltridecan-2-yl]oxycarbonylbenzoic acid
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005

文献信息

• The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution
  作者：Konstantin N. Prokhorevich、Oleg G. Kulinkovich

  DOI：10.1016/j.tetasy.2006.11.005

  日期：2006.11

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.