octan-2-yl 4-methoxybenzoate

• 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: octan-2-yl 4-methoxybenzoate
• 英文别名: 4-methoxy-benzoic acid-(1-methyl-heptyl ester)；4-Methoxy-benzoesaeure-(1-methyl-heptylester)；4-Methoxybenzoic acid, 2-octyl ester
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: MBWIVLMYWMIOJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  oct-1-en-2-yl 4-methoxybenzoate 在 1,1'-bis(diisopropylphosphino)ferrocene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 二氯甲烷 为溶剂， 40.0 ℃ 、400.01 kPa 条件下， 反应 24.0h， 生成 octan-2-yl 4-methoxybenzoate
  参考文献：
  名称：

  1-烷基乙烯基苯甲酸酯的高度对映选择性加氢：手性2-烷基醇的简单，非酶促途径

  摘要：

  走向手性！描述了通过使用带有P bearingOP配体的Rh催化剂对烯醇酯1的高度对映选择性催化氢化（参见方案； NBD ＝降冰片二烯）。该催化体系具有广泛的范围，并允许制备具有高对映选择性的各种带有各种烷基或苄基的手性酯2。这些酯可以很容易地转化为高度对映体富集的2-链烷醇。

  DOI：

  10.1002/chem.201303500

文献信息

• Generally applicable and efficient esterification of aldehydes with alcohols catalyzed by cyclopalladated ferrocenylimine
  作者：Gaizhi Ma、Yuting Leng、Huijie Qiao、Fan Yang、Shiwei Wang、Yangjie Wu

  DOI：10.1002/aoc.3069

  日期：2014.1

  The palladacycle‐catalyzed esterification of a variety of aldehydes with alcohols was developed. This reaction allows formation of esters in moderate to excellent yields not only for various aldehydes but also alcohols. In addition, the esterification could proceed well under mild conditions with a low catalyst loading of 0.0625 mol%. Copyright © 2013 John Wiley & Sons, Ltd.

  开发了由palladacycle催化的各种醛与醇的酯化反应。该反应使得不仅对于各种醛而且对于醇，都以中等至优异的产率形成酯。另外，在0.0625mol％的低催化剂负载下，酯化可以在温和的条件下很好地进行。版权所有©2013 John Wiley＆Sons，Ltd.
• Ligand-Assisted Rate Acceleration in Lanthanum(III) Isopropoxide Catalyzed Transesterification of Carboxylic Esters
  作者：Manabu Hatano、Yoshiro Furuya、Takumi Shimmura、Katsuhiko Moriyama、Sho Kamiya、Toshikatsu Maki、Kazuaki Ishihara

  DOI：10.1021/ol102753n

  日期：2011.2.4

  The transesterification of an equimolar mixture of carboxylic esters and primary (1 degrees), secondary (2 degrees), and tertiary (3 degrees) alcohols in hydrocarbon solvents was promoted with high efficiency by a lanthanum(III) complex, which was prepared in situ from lanthanum(III) isopropoxide (1 mol %) and 2-(2-methoxyethoxy)ethanol(2 mol %). The present La(III) catalyst was highly effective for the chemoselective transesterification in the presence of competitive 1 degrees- and 2 degrees-amines. Remarkably, esters were obtained in good to excellent yields as colorless materials without an inconvenient workup procedure.
• Microwave-Assisted Ester Formation Using <i>O</i>-Alkylisoureas: A Convenient Method for the Synthesis of Esters with Inversion of Configuration
  作者：Alessandra Chighine、Stefano Crosignani、Marie-Claire Arnal、Mark Bradley、Bruno Linclau

  DOI：10.1021/jo900476y

  日期：2009.7.3

  The formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas proceeds in excellent yields with very short reaction times when conducted in a monomode microwave synthesizer. Efficient processes were developed using preformed or commercially available isoureas derived from primary and secondary alcohols, with a reaction time of only 5 min or less. It was demonstrated that under these microwave conditions, ester formation proceeded in good yields with clean inversion of configuration where appropriate. The process was validated using menthol, a hindered substrate for S(N)2 reactions. In addition, starting from primary alcohols, ester formation was successfully accomplished using ail in situ isourea formation procedure. A polymer-assisted solution-phase procedure was also developed by employing preformed solid-supported isoureas and by an efficient "catch and release" ester formation procedure whereby primary alcohols were caught on resin as isoureas by reaction with immobilized carbodiimide and released as esters by subsequent treatment with a carboxylic acids.
• CCLXXX.—Optical activity and the polarity of substituent groups. Part IV. sec.-β-Octyl esters of o-, m-, and p-methoxy- and nitro-benzoic acids
  作者：Harold Gordon Rule、Annie Hutton Numbers

  DOI：10.1039/jr9262902116

  日期：——
• Highly Enantioselective Hydrogenation of 1-Alkylvinyl Benzoates: A Simple, Nonenzymatic Access to Chiral 2-Alkanols
  作者：Patryk Kleman、Pedro J. González-Liste、Sergio E. García-Garrido、Victorio Cadierno、Antonio Pizzano

  DOI：10.1002/chem.201303500

  日期：2013.11.25

  Going chiral! Highly enantioselective catalytic hydrogenations of enol esters 1 by using a Rh catalyst bearing a POP ligand are described (see scheme; NBD=norbornadiene). The catalytic system has a broad scope and allows the preparation of a wide range of chiral esters 2 bearing diverse alkyls or a benzyl group with high enantioselectivities. These esters can easily be converted in highly enantioenriched

  走向手性！描述了通过使用带有P bearingOP配体的Rh催化剂对烯醇酯1的高度对映选择性催化氢化（参见方案； NBD ＝降冰片二烯）。该催化体系具有广泛的范围，并允许制备具有高对映选择性的各种带有各种烷基或苄基的手性酯2。这些酯可以很容易地转化为高度对映体富集的2-链烷醇。