(S)-3-(2-methoxy-4-methylphenyl)butanoic acid | 246037-79-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-(2-methoxy-4-methylphenyl)butanoic acid
• 英文别名: (S)-3-(2-methoxy-4-methylphenyl)butyric acid；(3S)-3-(2-methoxy-4-methylphenyl)butanoic acid
• CAS: 246037-79-6
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: MMIMLZSFRVVPRU-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(2-methoxy-4-methylphenyl)butanoic acid 在 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-6-(2-hydroxy-4-methylphenyl)-2-methylhept-2-en-4-one
  参考文献：
  名称：

  Use of 1,1'-Binaphthalene-8,8'-diol as a Chiral Auxiliary for Asymmetric Michael Addition. Application to the Syntheses of Turmeronol A and B.

  摘要：

  二愈创木酸锂与 1，1'-联萘-8，8'-二醇的半酯进行高非对映选择性迈克尔加成反应，甲醇分解后得到对映体过量的 β-取代酯。以该反应为关键步骤，合成了具有光学活性的酚类倍半萜化合物松柏醇 A (1) 和 B(2)。

  DOI：

  10.1248/cpb.47.1053
• 作为产物：
  描述：

  (R)-2-(2-methoxy-4-methylphenyl)propan-1-ol 在 吡啶 、 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 19.0h， 生成 (S)-3-(2-methoxy-4-methylphenyl)butanoic acid
  参考文献：
  名称：

  Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes

  摘要：

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.012

文献信息

• Diastereoselective hydrogenation of α,β-unsaturated but-2-enamides to access the chiral 3-(p-tolyl) butanoic acids
  作者：Jacqueline Jiménez、Mildred López、Vladimir Carranza、Angel Mendoza、Jenaro Varela、Estibaliz Sansinenea、Aurelio Ortiz

  DOI：10.1016/j.tetlet.2016.12.017

  日期：2017.1

  An alternative methodology for the synthesis of chiral 3-(p-tolyl) butanoic acids is presented. This was accomplished through the diastereoselective hydrogenation reaction of different chiral N-3-(p-tolyl) but-2-enamides, using Pd/C in EtOH, to produce the corresponding chiral N-3-(p-tolyl) butanamides with high chemical yields and moderate diastereomeric ratios. Removal of the chiral auxiliary from

  提出了合成手性3-（对甲苯基）丁酸的另一种方法。这是通过在EtOH中使用Pd / C对不同的手性N -3-（对甲苯基）丁-2-烯酰胺进行非对映选择性氢化反应来生产相应的手性N -3-（对甲苯基）丁酰胺而得到的化学收率和适度的非对映异构体比率。从N -3-（对甲苯基）丁酰胺中除去手性助剂，得到相应的对映体纯酸。
• Use of 1,1'-Binaphthalene-8,8'-diol as a Chiral Auxiliary for Asymmetric Michael Addition. Application to the Syntheses of Turmeronol A and B.
  作者：Kiyoshi TANAKA、Mohammad NURUZZAMAN、Masato YOSHIDA、Naoyuki ASAKAWA、Xiao-Shen YANG、Kazunori TSUBAKI、Kaoru FUJI

  DOI：10.1248/cpb.47.1053

  日期：——

  Highly diastereoselective Michael addition of lithium diorganocuprates to the half-ester of 1, 1'-binaphthalene-8, 8'-diol gave β-substituted esters with high enantiomeric excess after methanolysis. The optically active phenolic sesquiterpenes turmeronol A (1) and B(2) have been synthesized using this reaction as a key step.

  二愈创木酸锂与 1，1'-联萘-8，8'-二醇的半酯进行高非对映选择性迈克尔加成反应，甲醇分解后得到对映体过量的 β-取代酯。以该反应为关键步骤，合成了具有光学活性的酚类倍半萜化合物松柏醇 A (1) 和 B(2)。
• Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol: an efficient chemoenzymatic route
  作者：Ahmed Kamal、M. Shaheer Malik、Ahmad Ali Shaik、Shaik Azeeza

  DOI：10.1016/j.tetasy.2007.10.019

  日期：2007.10

  An efficient enantioselective synthesis of curcumene and curcuphenol is described. The key intermediates, substituted butanoates 7a and 7b and their acids 8a and 8b are obtained in high enantiopurity (>99% eel by a lipase-catalyzed kinetic resolution process. The enantiopure intermediates thus obtained were utilized for the total synthesis of the target compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2011.03.012

  日期：2011.3

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.