(R)-octan-2-yl 3-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: (R)-octan-2-yl 3-methoxybenzoate
• 英文别名: [(2R)-octan-2-yl] 3-methoxybenzoate
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: PFNZITXAXFDVSP-CYBMUJFWSA-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 3-methoxybenzoate 在 C₃₈H₄₆O₃P₂*C₇H₈*Rh⁽¹⁺⁾*BF₄^(1-) 、 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， 以95%的产率得到(R)-octan-2-yl 3-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

• 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。
• Asymmetric Hydrogenation of 1-Alkyl and 1-Aryl Vinyl Benzoates: A Broad Scope Procedure for the Highly Enantioselective Synthesis of 1-Substituted Ethyl Benzoates
  作者：Patryk Kleman、Pedro J. González-Liste、Sergio E. García-Garrido、Victorio Cadierno、Antonio Pizzano

  DOI：10.1021/cs501402z

  日期：2014.12.5

  The enantioselective hydrogenation of enol esters of formula CH2=C(OBz)R with rhodium catalysts based on phosphine phosphite ligands (P-OP) has been studied. The reaction has a broad scope, and it is suitable for the preparation of products possessing a wide variety of R substituents. For the cases where R is a primary alkyl, high catalyst activity (S/C = 500) and enantioselectivities (95-99% ee) were obtained with a catalyst characterized by an ethane backbone and a PPh2 fragment. In contrast, for R = t-Bu, a catalyst possessing a benzene backbone provided the best results (97% ee). Derivatives with a cycloalkyl R substituent were particularly difficult substrates for this reaction. A broader catalyst screening was required for these substrates, which identified a catalyst possessing a P(m-xylyl)(2) fragment as the most appropriate one, affording enantioselectivities between 90 and 95% ee. Outstanding enantioselectivities (99% ee) and high catalyst activity (S/C = 500-1000) were also obtained in the case of substrates bearing a Ph or a fluoroaryl R substituent. In addition, the system is also appropriate for the preparation of other synthetically useful esters as those for R = benzyl, 2-phenylethyl or N-phthalimido alkyl chains. Likewise, the hydrogenation of divinyl dibenzoates proceeded with very high diastero- and enantioselectivity, generating rather low amounts of the meso isomer (3-6%). On the other hand, substrates with Br and MeO substituents at the phenyl benzoate ring, suitable for further functionalization, have also been examined. The results obtained indicate no detrimental effect of these substituents in the hydrogenation. Alternatively, the methodology has been applied to the highly enantioselective synthesis of deuterium isotopomers of 1-octyl benzoate bearing CDH2, CD2H, or CD3 fragments. Finally, as a practical advantage of the present system, it has been observed that the high performance of the catalysts is retained in highly concentrated solutions or even in the neat substrate, minimizing both the amount of solvent added and the volume of the reaction.