(R)-(-)-methyl 3-phenyl-2-ethylpropionate | 138809-62-8

• 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: (R)-(-)-methyl 3-phenyl-2-ethylpropionate
• 英文别名: R-methyl 2-benzylbutyrate；methyl (2R)-2-benzylbutanoate
• CAS: 138809-62-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: HMZORGBBZUEAFG-LLVKDONJSA-N

物化性质

• 沸点：
  258.5±9.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (R)-(-)-methyl 3-phenyl-2-ethylpropionate 在 palladium on activated charcoal 乙醇 、 硫酸 、 硝酸 、 四氯化钛 、 potassium carbonate 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-2-(3-Formyl-4-methoxy-benzyl)-butyric acid methyl ester
  参考文献：
  名称：

  Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha

  摘要：

  Optically active phenylpropanoic acid derivatives [(S)-5. and (R)-5] were prepared, and their affinities for peroxisome proliferator-activated receptor (PPAR)alpha and PPARgamma were evaluated. Binding assay and cell-based reporter assay indicated that the activity of these compounds is enantio-dependent, and resides exclusively on the (S)-isomer. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00732-6
• 作为产物：
  描述：

  (+/-)-3-m-nitrophenyl-2-ethylpropionic acid 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 亚膦酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 (R)-(-)-methyl 3-phenyl-2-ethylpropionate
  参考文献：
  名称：

  Chemoenzymatic synthesis of the enantiomers of iopanoic acid

  摘要：

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.

  DOI：

  10.1016/s0957-4166(00)86152-2

文献信息

• Asymmetric Synthesis of α-Alkylated <i>N</i>-Sulfinyl Imidates as New Chiral Building Blocks
  作者：Filip Colpaert、Sven Mangelinckx、Guido Verniest、Norbert De Kimpe

  DOI：10.1021/jo900046t

  日期：2009.5.15

  outstanding yields. These imidate hydrochlorides proved to be excellent intermediates for an easy transformation to chiral amides in good yields and enantiomeric excess upon simple heating in chloroform. Hydrolysis of the α-benzylated imidate hydrochlorides afforded the corresponding chiral esters with >95% ee.

  通过叔丁烷亚磺酰胺与原酸酯的缩合反应制得的N-亚磺酰亚胺基的α-烷基化反应可生成非对映异构体比率优良的α-取代的N-亚磺酰亚胺基（dr高达> 99：1），收率很高。烷基化的N-亚硫酰亚胺基的去保护基使得能够以优异的产率得到相应的亚氨酸盐酸盐。这些亚氨酸盐酸盐被证明是极好的中间体，易于在氯仿中简单加热，容易以高收率转化成手性酰胺，而对映体过量。水解α-苄基亚氨酸盐酸盐，得到相应的手性酯，其ee＞ 95％。
• A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide–carbonate systems for synthesis of planar-chiral nicotinate
  作者：Nobuhiro Kanomata、Satoshi Maruyama、Katsuhito Tomono、Shinnosuke Anada

  DOI：10.1016/s0040-4039(03)00698-1

  日期：2003.4

  A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidin one and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Chemoenzymatic synthesis of the enantiomers of iopanoic acid
  作者：M. Colombo、M. De Amici、C. De Micheli、D. Pitré、G. Carrea、S. Riva

  DOI：10.1016/s0957-4166(00)86152-2

  日期：1991.1

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.
• Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha
  作者：Hiroyuki Miyachi、Masahiro Nomura、Takahiro Tanase、Masahiro Suzuki、Koji Murakami、Katsuya Awano

  DOI：10.1016/s0960-894x(01)00732-6

  日期：2002.2

  Optically active phenylpropanoic acid derivatives [(S)-5. and (R)-5] were prepared, and their affinities for peroxisome proliferator-activated receptor (PPAR)alpha and PPARgamma were evaluated. Binding assay and cell-based reporter assay indicated that the activity of these compounds is enantio-dependent, and resides exclusively on the (S)-isomer. (C) 2002 Elsevier Science Ltd. All rights reserved.