(E)-10-Acetoxy-dec-8-enoic acid methyl ester

• 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: (E)-10-Acetoxy-dec-8-enoic acid methyl ester
• 英文别名: Methyl 10-acetyloxydec-8-enoate；methyl 10-acetyloxydec-8-enoate
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: BGWZCBULBOYBIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-10-Acetoxy-dec-8-enoic acid methyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 methyl 10-hydroxy-(Z)-dec-8-enoate 、 (8E)-10-hydroxydec-8-enoic acid methyl ether
  参考文献：
  名称：

  烃氧化与CC键形成方法可有效合成含氧分子。

  摘要：

  [反应：见正文]烃氧化方法已用于构建几种线性（E）-烯丙基醇，这些醇在合成天然产物和类似天然产物的分子中用作中间体。在最初的合成中，这些中间体是使用标准的Wittig型烯化方法构建的。我们在此报告，围绕官能团氧化方法设计的相同中间体的路线，在官能团操作（FGM）的总数和总体步骤以及总收率上均更为有效。

  DOI：

  10.1021/ol047800p

文献信息

• [EN] CATALYTIC SULFOXIDE-PROMOTED C-H OXIDATION, AND REGIOSELECTIVE PREPARATION OF ALLYLIC CARBOXYLATES<br/>[FR] OXYDATION C-H CATALYTIQUE PAR SULFOXYDE ET PREPARATION REGIOSELECTIVE DE CARBOXYLATES ALLYLIQUES
  申请人：HARVARD COLLEGE

  公开号：WO2005062811A2

  公开（公告）日：2005-07-14

  One aspect of the present invention relates to a method of preparing allylic carboxylate compounds comprising the step of contacting a compound comprising an allylic hydrogen atom with a carboxylic acid in the presence of palladium, a sulfoxide compound, and an oxidant. For example, the instant invention provides a catalytic method for the direct C-H oxidation of monosubstituted olefins to prepare linear (E)-allylic acetates in high regio- and stereoselectivities. In addition, the method of the instant invention can be used to prepare branched allylic carboxylates with high yield and regioselectivity. Another aspect of the present invention relates to sulfoxide compounds that are useful as catalysts to effect C-H oxidation. Remarkably, the allylic oxidation method of the invention is compatible with a wide range of functionality, such as amides, carbamates, carbonates, esters, and ethers.
• Hydrocarbon Oxidation vs C−C Bond-Forming Approaches for Efficient Syntheses of Oxygenated Molecules
  作者：Kenneth J. Fraunhoffer、Daniel A. Bachovchin、M. Christina White

  DOI：10.1021/ol047800p

  日期：2005.1.1

  [Reaction: see text] A hydrocarbon oxidation approach has been applied to the construction of several linear (E)-allylic alcohols that have served as intermediates in the synthesis of natural products and natural product-like molecules. In the original syntheses, these intermediates were constructed using a standard Wittig-type olefination approach. We report here that routes to these same intermediates

  [反应：见正文]烃氧化方法已用于构建几种线性（E）-烯丙基醇，这些醇在合成天然产物和类似天然产物的分子中用作中间体。在最初的合成中，这些中间体是使用标准的Wittig型烯化方法构建的。我们在此报告，围绕官能团氧化方法设计的相同中间体的路线，在官能团操作（FGM）的总数和总体步骤以及总收率上均更为有效。