4-chloro-α-(1-methylethyl)-β-oxo-benzenepropanoic acid ethyl ester | 226416-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-chloro-α-(1-methylethyl)-β-oxo-benzenepropanoic acid ethyl ester
• 英文别名: 2-(4-Chlorobenzoyl)isovaleric acid ethyl ester；Ethyl 2-(4-chlorobenzoyl)-3-methylbutanoate
• CAS: 226416-31-5
• 化学式: C₁₄H₁₇ClO₃
• mdl: MFCD16502392
• 分子量: 268.74
• InChiKey: FPDVHQBRLUEWPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 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-chloro-α-(1-methylethyl)-β-oxo-benzenepropanoic acid ethyl ester 、 苯胺 以 邻二甲苯 为溶剂， 以40%的产率得到2-(4-chlorobenzoyl)-3-methyl-N-phenylbutanamide
  参考文献：
  名称：

  N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor

  摘要：

  A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R-1 moiety and at the warhead, while the R-2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.032
• 作为产物：
  描述：

  异戊酸乙酯 、 4-氯苯甲酰氯 以to obtain the title compound (2.2 g, 82%) as a colorless oil的产率得到4-chloro-α-(1-methylethyl)-β-oxo-benzenepropanoic acid ethyl ester
  参考文献：
  名称：

  Isoxazole compounds useful for the prophylaxis or treatment of nervous

  摘要：

  具有以下一般式的异噁唑化合物：##STR1## 其中 R.sup.1 代表可选取代的芳基或芳香杂环基；R.sup.2 代表氢原子、卤原子、可选取代的烷基、烯基、炔基、环烷基、环烯基、烷氧基、氰基、羧基、酰基、烷氧羰基或可选取代的氨基甲酰基；R.sup.3 代表可选取代的氨基或饱和杂环基；X 代表氧原子或硫原子；n 为2到6的整数。这些化合物具有出色的单胺氧化酶抑制活性，并可用作治疗剂或预防神经疾病如抑郁症的药物。

  公开号：

  US06005116A1

文献信息

• ISOXAZOLE DERIVATIVES
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0885891A1

  公开（公告）日：1998-12-23

  The isoxazole derivatives having the following general formula: [wherein R1 represents an optionally substituted aryl group or aromatic heterocyclic group; R2 represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a cyano group, a carboxyl group, an alkanoyl group, an alkoxycarbonyl group or an optionally substituted carbamoyl group; R3 represents an optionally substituted amino group or a saturated heterocyclic group; X represents an oxygen atom or a sulfur atom; n is an integer of from 2 to 6] has an excellent monoamine oxidase inhibitory activity, and is useful as a therapeutic agent or a preventive agent against nervous diseases such as depression.

  具有以下通式的异噁唑衍生物： [其中 R1 代表任选取代的芳基或芳香杂环基团；R2 代表氢原子、卤素原子、任选取代的烷基、烯基、炔基、环烷基、环烯基、烷氧基、氰基、羧基、烷酰基、烷氧羰基或任选取代的氨基甲酰基；R3 代表任选取代的氨基或饱和杂环基团；X 代表氧原子或硫原子；n 为 2 至 6 的整数]具有极佳的单胺氧化酶抑制活性，可用作治疗剂或预防剂，防治抑郁症等神经疾病。
• US6005116A
  申请人：——

  公开号：US6005116A

  公开（公告）日：1999-12-21
• N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor
  作者：Karl S.A. Vallin、Karin J. Sterky、Eva Nyman、Jenny Bernström、Rebecka From、Christian Linde、Alexander B.E. Minidis、Andreas Nolting、Katja Närhi、Ellen M. Santangelo、Fernando W. Sehgelmeble、Daniel Sohn、Jennie Strindlund、Dirk Weigelt

  DOI：10.1016/j.bmcl.2012.07.032

  日期：2012.9

  A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R-1 moiety and at the warhead, while the R-2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone. (c) 2012 Elsevier Ltd. All rights reserved.
• Isoxazole compounds useful for the prophylaxis or treatment of nervous
  申请人：Sankyo Company, Limited

  公开号：US06005116A1

  公开（公告）日：1999-12-21

  Isoxazole compounds having the following general formula: ##STR1## wherein R.sup.1 represents an optionally substituted aryl group or aromatic heterocyclic group; R.sup.2 represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, an alkoxy group, a cyano group, a carboxyl group, an alkanoyl group, an alkoxycarbonyl group or an optionally substituted carbamoyl group; R.sup.3 represents an optionally substituted amino group or a saturated heterocyclic group; X represents an oxygen atom or a sulfur atom; and n is an integer of from 2 to 6. These compounds have excellent monoamine oxidase inhibitory activity and are useful as a therapeutic agent or a preventive agent against nervous diseases such as depression.

  异噁唑化合物具有以下一般式：##STR1##其中R.sup.1代表可选择取代的芳基或芳香杂环基；R.sup.2代表氢原子、卤素原子、可选择取代的烷基、烯基、炔基、环烷基、环烯基、烷氧基、氰基、羧基、烷酰基、烷氧羰基或可选择取代的氨基甲酰基；R.sup.3代表可选择取代的氨基或饱和杂环基；X代表氧原子或硫原子；n为2到6的整数。这些化合物具有优异的单胺氧化酶抑制活性，并可用作治疗剂或预防剂，用于抑郁等神经疾病。