4-(对甲基苯基)-2-氧代丁酸乙酯 | 83402-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(对甲基苯基)-2-氧代丁酸乙酯
• 英文名称: ethyl 4-(p-methylphenyl)-2-oxobutyrate
• 英文别名: ethyl 2-oxo-4-(p-tolyl)butyrate；ethyl-2-oxo-4-phenylbutyrate；ethyl 4-(4-methylphenyl)-2-oxobutanoate
• CAS: 83402-93-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: LEMTZBIOTKZQEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(对甲基苯基)-2-氧代丁酸乙酯 在 lithium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 4-(p-methylphenyl)-2-oxobutanoic acid
  参考文献：
  名称：

  Highly enantioselective hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids

  摘要：

  The Ru-catalyzed asymmetric hydrogenation of 2-oxo-4-arybutanoic acids to afford 2-hydroxy-4-arybutanoic acids was accomplished by employing SunPhos as chiral ligand and 1 M aq HBr as additive. The high enantioselectivities (88.4%-92.6% ee) and efficiency (TON=10,000, TOF=300 h(-1)) make this method efficient for the synthesis of an important intermediate, (R)-2-hydroxy-4-phenylbutanoic acid, for ACE inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.071
• 作为产物：
  描述：

  2-Hydroxy-4-p-tolyl-butyric acid ethyl ester 在 2,2,6,6-四甲基哌啶氧化物 、 calcium methylate 作用下， 以 乙腈 为溶剂， 以97%的产率得到4-(对甲基苯基)-2-氧代丁酸乙酯
  参考文献：
  名称：

  TEMPO 催化氧化的简化程序：使用 TEMPO 和次氯酸钙选择性氧化醇、α-羟基酯和酰胺

  摘要：

  摘要 在温和的反应条件下，使用 2,2,6,6-四甲基哌啶将多种伯多官能团醇、α-羟基酰胺和 α-羟基酯氧化成相应的醛、酮、α-酮酰胺和 α-酮酯。 -1-氧基作为催化剂，次氯酸钙作为氧化剂[TEMPO-Ca(OCl)2]。这种简化的方法不需要任何过渡金属、酸或碱，并且展示了结构多样的醇的受控和选择性氧化，在室温下提供中等至极好的收率。图形概要

  DOI：

  10.1080/00397911.2011.584650

文献信息

• Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions
  作者：Duc Hai Dao、Mutsuo Okamura、Takeshi Akasaka、Yasushi Kawai、Kouichi Hida、Atsuyoshi Ohno

  DOI：10.1016/s0957-4166(98)00277-8

  日期：1998.8

  Treatment of baker's yeast with phenacyl chloride in an aqueous–organic solvent has been proven to be an effective method of inhibiting the enzymes that afford (S)-enantiomers of α-hydroxy esters in the reduction of α-keto esters. The procedure is effective for the whole-cell system to produce the (R)-product with high chemical yield and high enantiomeric excess.

  已证明在水-有机溶剂中用苯甲酰氯处理面包酵母是抑制α-羟基酯还原中提供α-羟基酯的（S）-对映异构体的酶的有效方法。该方法对于全细胞系统生产具有高化学产率和高对映体过量的（R）产物是有效的。
• Condensed, seven-membered ring compounds and their use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04564612A1

  公开（公告）日：1986-01-14

  Novel condensed, seven-membered ring compounds of the formula: ##STR1## [wherein R.sup.1 and R.sup.2 each represent hydrogen, halogen, trifluoromethyl, lower alkyl or alkoxy, or both jointly form tri- or tetramethylene; R.sup.3 is hydrogen, lower alkyl or aralkyl; R.sup.4 is hydrogen or alkyl, aralkyl or cycloalkylalkyl which may be substituted; X is a group represented by the formula S(O).sub.n (where n is an integer of 0 to 2); Y is a carboxyl group which may be esterified or amidated; m is 1 or 2] and salts thereof. These compounds exhibit inhibitory activity on angiotensin converting enzyme and so forth, and are of value as an agent for diagnosis, prevention and treatment of hypertension.

  这些小说中的新型缩合七元环化合物的化学式为：[其中R.sup.1和R.sup.2分别表示氢、卤素、三氟甲基、低碳基或烷氧基，或者共同形成三元或四元亚甲基；R.sup.3为氢、低碳基或芳基烷基；R.sup.4为氢或烷基、芳基烷基或环烷基烷基，可被取代；X为由S(O).sub.n（其中n为0至2的整数）表示的基团；Y为可酯化或酰胺化的羧基；m为1或2]及其盐。这些化合物表现出对血管紧张素转换酶等的抑制活性，并且在高血压的诊断、预防和治疗方面具有价值。
• Cross-Aldol Reaction of Activated Carbonyls with Nitrosocarbonyl Intermediates: Stereoselective Synthesis toward α-Hydroxy-β-amino Esters and Amides
  作者：Sumitava Mallik、Vinod Bhajammanavar、Isai Ramakrishna、Mahiuddin Baidya

  DOI：10.1021/acs.orglett.7b01721

  日期：2017.7.21

  practical and flexible strategy toward α-hydroxy-β-amino esters and amides, which are important biological motifs, based on an organocatalytic cross-aldol reaction of in situ-generated nitrosocarbonyl intermediates followed by hydrogenation is presented. The protocol features operational simplicity, high yields, a wide substrate scope, and high regio- and diastereoselectivity profiles. The utility of

  基于原位生成的亚硝基羰基中间体的有机催化交叉羟醛反应，然后氢化，提出了一种重要的生物学基序-α-羟基-β-氨基酯和酰胺的实用且灵活的策略。该协议具有操作简便，产率高，底物范围广，区域选择性和非对映选择性高的特点。通过Bestest类似物的合成和吲哚的形成展示了该方法的实用性。
• Modulation of anxiety through blockade of anandamide hydrolysis
  申请人：Piomelli Daniele

  公开号：US20090048337A1

  公开（公告）日：2009-02-19

  Fatty acid amide hydrolase inhibitors of the Formula: I. are provided wherein X is NH, CH 2 , O, or S; Q is O or S; Z is O or N; R is an aromatic moiety selected from the group consisting of substituted or unsubstituted aryl; substituted or unsubstituted biphenylyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenyl; substituted or unsubstituted terphenylyl; substituted or unsubstituted cycloalkyl, heteroaryl, or alkyl; and R 1 and R 2 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, and substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; with the proviso that if Z is O, one of R 1 and R 2 is absent, and that if Z is N, optionally R 1 and R 2 may optionally be taken together to form a substituted or unsubstituted N-heterocycle or substituted or unsubstituted heteroaryl with the N atom to which they are each attached. Pharmaceutical compositions comprising the compounds of Formula I and methods of using them to inhibit FAAH and/or treat appetite disorders, glaucoma, pain, insomnia, and neurological and psychological disorders including anxiety disorders, epilepsy, and depression are provided.

  提供了公式为I的脂肪酸酰胺水解酶抑制剂，其中X为NH，CH2，O或S; Q为O或S; Z为O或N; R为从取代或未取代芳基; 取代或未取代的联苯基; 取代或未取代的萘基; 取代或未取代的苯基; 取代或未取代的三苯基基; 取代或未取代的环烷基，杂环芳基或烷基中选择的芳香基；R1和R2独立地选择自H，取代或未取代的烷基，取代或未取代的杂环烷基，取代或未取代的苯基，取代或未取代的联苯基，取代或未取代的芳基，取代或未取代的杂环芳基的群体中；但如果Z为O，则R1和R2中的一个不存在，如果Z为N，则可选地将R1和R2结合在一起形成取代或未取代的N-杂环或取代或未取代的杂环芳基，与它们各自连接的N原子。提供了包含公式I化合物的药物组合物以及使用它们抑制FAAH和/或治疗食欲障碍，青光眼，疼痛，失眠以及神经和心理障碍，包括焦虑症，癫痫和抑郁症的方法。
• MODULATION OF ANXIETY THROUGH BLOCKADE OF ANANDAMIDE HYDROLYSIS
  申请人：Piomelli Daniele

  公开号：US20120010283A1

  公开（公告）日：2012-01-12

  Fatty acid amide hydrolase inhibitors of the Formula: are provided wherein X is NH, CH 2 , O, or S; Q is O or S; Z is O or N; R is an aromatic moiety selected from the group consisting of substituted or unsubstituted aryl; substituted or unsubstituted biphenylyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenyl; substituted or unsubstituted terphenylyl; substituted or unsubstituted cycloalkyl, heteroaryl, or alkyl; and R 1 and R 2 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, and substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; with the proviso that if Z is O, one of R 1 and R 2 is absent, and that if Z is N, optionally R 1 and R 2 may optionally be taken together to form a substituted or unsubstituted N-heterocycle or substituted or unsubstituted heteroaryl with the N atom to which they are each attached. Pharmaceutical compositions comprising the compounds of Formula I and methods of using them to inhibit FAAH and/or treat appetite disorders, glaucoma, pain, insomnia, and neurological and psychological disorders including anxiety disorders, epilepsy, and depression are provided.

  提供了公式为的脂肪酸酰胺水解酶抑制剂：其中X为NH，CH2，O或S；Q为O或S；Z为O或N；R为从取代或未取代芳基；取代或未取代联苯基；取代或未取代萘基；取代或未取代苯基；取代或未取代三苯基基；取代或未取代环烷基，杂环芳基或烷基中选择的芳香基；R1和R2分别选择自H，取代或未取代烷基，取代或未取代杂环烷基，取代或未取代苯基，取代或未取代联苯基，取代或未取代芳基和取代或未取代杂环芳基的群中；但是如果Z为O，则R1和R2中的一个不存在，如果Z为N，则可选地将R1和R2结合在一起形成取代或未取代的N-杂环或取代或未取代的杂环芳基，与它们各自连接的N原子。提供了包含公式I化合物的制药组合物以及使用它们来抑制FAAH和/或治疗食欲障碍，青光眼，疼痛，失眠以及神经和心理障碍，包括焦虑症，癫痫和抑郁症的方法。