Undecen-(1)-saeure-(11)-<4-chlorphenylester> | 93738-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Undecen-(1)-saeure-(11)-<4-chlorphenylester>
• 英文别名: 10-undecenic acid 4-chlorophenyl ester；(4-Chlorophenyl) undec-10-enoate
• CAS: 93738-25-1
• 化学式: C₁₇H₂₃ClO₂
• 分子量: 294.821
• InChiKey: AWDIPJXFFBNZBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯乙醇 、 Undecen-(1)-saeure-(11)-<4-chlorphenylester> 在 tetrabutylammonium tricarbonylnitrosylferrate 作用下， 以 正己烷 为溶剂， 以83%的产率得到2-苯基乙基十一碳-10-烯酸酯
  参考文献：
  名称：

  Nucleophilic Iron Catalysis in Transesterifications: Scope and Limitations

  摘要：

  The ester bond is one of the most common structural motifs found in nature. Apart from the condensation between an acid and an alcohol, transesterifications represent another mechanistic alternative for the preparation of this compound class. The present paper summarizes our most recent investigations in this field, using nucleophilic iron complexes as catalysts for transesterifications under neutral conditions. This new type of metal catalyst complements the existing methodologies, which rely on Lewis acidic metal complexes. Investigations on scope and limitations, stereochemical course, and chemoselectivities will be presented.

  DOI：

  10.1021/jo1004636
• 作为产物：
  描述：

  2-十一烯酸 、 对氯苯酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到Undecen-(1)-saeure-(11)-<4-chlorphenylester>
  参考文献：
  名称：

  铁催化的羧酸酯硫酯化反应

  摘要：

  第二性质：从稳定的芳基酯和硫醇开始，各种羧酸酯被转化为相应的硫酯，而没有外消旋的立体中心（见方案）。该方法已成功地用于天然化学连接型肽的形成，这表明硫醇可能会作为亲核试剂将来向羧酸酯中添加1,2的助催化剂。

  DOI：

  10.1002/chem.201101073

文献信息

• Popova,E.G., Journal of general chemistry of the USSR, 1964, vol. 34, p. 2692 - 2694
  作者：Popova,E.G.

  DOI：——

  日期：——
• Fe-Catalyzed Thioesterification of Carboxylic Esters
  作者：Silja Magens、Bernd Plietker

  DOI：10.1002/chem.201101073

  日期：2011.8.1

  shelf‐stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical‐ligation‐type peptide formation, which suggests that the thiol may act as a co‐catalyst for future 1,2‐additions of pronucleophiles to carboxylic esters.

  第二性质：从稳定的芳基酯和硫醇开始，各种羧酸酯被转化为相应的硫酯，而没有外消旋的立体中心（见方案）。该方法已成功地用于天然化学连接型肽的形成，这表明硫醇可能会作为亲核试剂将来向羧酸酯中添加1,2的助催化剂。
• Nucleophilic Iron Catalysis in Transesterifications: Scope and Limitations
  作者：Silja Magens、Bernd Plietker

  DOI：10.1021/jo1004636

  日期：2010.6.4

  The ester bond is one of the most common structural motifs found in nature. Apart from the condensation between an acid and an alcohol, transesterifications represent another mechanistic alternative for the preparation of this compound class. The present paper summarizes our most recent investigations in this field, using nucleophilic iron complexes as catalysts for transesterifications under neutral conditions. This new type of metal catalyst complements the existing methodologies, which rely on Lewis acidic metal complexes. Investigations on scope and limitations, stereochemical course, and chemoselectivities will be presented.