(S)-3-(4-chlorophenyl)-glutaric acid monomethyl ester | 865366-99-0

• 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-(4-chlorophenyl)-glutaric acid monomethyl ester
• 英文别名: (S)-3-(4-chlorophenyl)-5-methoxy-5-oxopentanoic acid；(3S)-3-(4-chlorophenyl)-5-methoxy-5-oxopentanoic acid
• CAS: 865366-99-0
• 化学式: C₁₂H₁₃ClO₄
• 分子量: 256.686
• InChiKey: KQOHPBYSQAUWTR-VIFPVBQESA-N

物化性质

• 熔点：
  100-101.5 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  395.9±32.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-chlorophenyl)-glutaric acid monomethyl ester 生成 R(+)-巴氯芬盐酸盐
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of baclofen

  摘要：

  Both enantiomers of baclofen have been synthesized in five steps from 4-chlorocinnamic acid. The key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin.

  DOI：

  10.1016/s0040-4039(00)92140-3
• 作为产物：
  描述：

  对氯肉桂酸 在 Dowex H+ resin sodium methylate 、 sodium chloride 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 生成 (S)-3-(4-chlorophenyl)-glutaric acid monomethyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of baclofen

  摘要：

  Both enantiomers of baclofen have been synthesized in five steps from 4-chlorocinnamic acid. The key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin.

  DOI：

  10.1016/s0040-4039(00)92140-3

文献信息

• Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of<i>meso</i>Cyclic Anhydrides
  作者：Lin-Jie Yan、Hai-Feng Wang、Wen-Xue Chen、Yuan Tao、Kai-Jun Jin、Fen-Er Chen

  DOI：10.1002/cctc.201600228

  日期：2016.7.6

  chloramphenicol‐base‐derived thiourea organocatalysts, (1S,2R)‐12 a–f and (1R,2R)‐15 a–c, and their use in the enantioselective alcoholysis of meso‐anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)‐12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)‐15 a–c. This technique was used to synthesize (R)‐(−)‐baclofen

  新的氯霉素基硫脲有机催化剂（1 S，2 R）-12 a - f和（1 R，2 R）15 a - c的合成及其在介孔酸酐的对映选择性醇解中的应用描述。特别是，如果使用低负荷的（1 S，2 R）-12 a – f负载，半酯具有出色的对映选择性。使用（1 R，2 R）‐ 15 a – c几乎没有达到对映选择性。该技术用于合成（R）-（-）-baclofen。
• Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of<i>meso</i>-cyclic anhydrides
  作者：Lingjun Xu、Shuwen Han、Linjie Yan、Haifeng Wang、Haihui Peng、Fener Chen

  DOI：10.3762/bjoc.14.19

  日期：——

  possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

  研发了一系列新型的氯霉素基础酰胺有机催化剂，它们在C-1位置具有NH官能团作为单齿氢键供体，并评估了其对中环酸酐的对映选择性有机催化醇解作用。发现这些结构多样的有机催化剂在酸酐的醇解中诱导高对映选择性，并成功地用于（S）-GABOB的不对称合成。
• An efficient synthesis of (R)- and (S)-baclofen via desymmetrization
  作者：Lei Ji、Yuheng Ma、Jin Li、Liangren Zhang、Lihe Zhang

  DOI：10.1016/j.tetlet.2009.08.079

  日期：2009.11

  A short and highly enantioselective synthesis of both enantiomers of GABA agonist baclofen in four steps with total yields of 32.8% [for (S)-isomer] and 35.1% [for (R)-isomer] is reported. The key step involved desymmetrization of cyclic anhydride with modified cinchona alkaloids.

  报道了GABA激动剂巴氯芬的两种对映体的短且高对映选择性的合成，其分四步进行，其总产率为（S）-异构体为32.8％[ R ]-异构体为35.1％。关键步骤涉及用修饰的金鸡纳生物碱使环酐脱对称化。
• Enzymatic desymmetrization of 3-arylglutaric acid anhydrides
  作者：Anna Fryszkowska、Marta Komar、Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2005.06.025

  日期：2005.7

  Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4. (C) 2005 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of both enantiomers of baclofen
  作者：Robert Chênevert、Michel Desjardins

  DOI：10.1016/s0040-4039(00)92140-3

  日期：1991.1

  Both enantiomers of baclofen have been synthesized in five steps from 4-chlorocinnamic acid. The key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin.