2-(4-氯苯甲酰基)-2-甲基丙酸乙酯 | 181067-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(4-氯苯甲酰基)-2-甲基丙酸乙酯
• 英文名称: ethyl 3-(4-chlorophenyl)-2,2-dimethyl-3-oxopropanoate
• 英文别名: Ethyl alpha-(4-chlorobenzoyl)isobutyrate
• CAS: 181067-68-5
• 化学式: C₁₃H₁₅ClO₃
• 分子量: 254.713
• InChiKey: DIQRGHUHNUKWEO-UHFFFAOYSA-N

物化性质

• 沸点：
  179-180 °C(Press: 20 Torr)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 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：

  2-(4-氯苯甲酰基)-2-甲基丙酸乙酯 在 硫酸 、 水 、 溶剂黄146 作用下， 生成 对氯苯异丁酮
  参考文献：
  名称：

  A Reformatsky Type Condensation of Aroyl Chlorides with Ethyl α-Bromoisobutyrate by Means of Zinc to Form β-Keto Esters^1,2

  摘要：

  DOI：

  10.1021/ja01638a007
• 作为产物：
  描述：

  碘甲烷 、 (4-氯苯甲酰基)乙酸乙酯 在 sodium hydride 作用下， 反应 12.5h， 生成 2-(4-氯苯甲酰基)-2-甲基丙酸乙酯
  参考文献：
  名称：

  通过将正式的双碳插入到 β-酮酯中轻松合成 δ-酮酯

  摘要：

  已经开发了一种正式的用乙烯基金属将双碳插入到β-酮酯中的方法，用于快速合成δ-酮酯。该方法具有效率高、操作简单、条件温和等特点，无需使用碱和催化剂。假设该反应通过串联过程进行，包括乙烯基金属与酮的亲核加成、逆醛醇反应产生烯醇化物阴离子和烯酮，最后是这两种中间体的迈克尔加成。

  DOI：

  10.1016/j.tetlet.2022.153656

文献信息

• Synthesis of 2<i>H</i> -Azirines by Iridium-Catalyzed Decarboxylative Ring Contraction of Isoxazol-5(4<i>H</i> )-ones
  作者：Kazuhiro Okamoto、Takuya Shimbayashi、Masato Yoshida、Atsushi Nanya、Kouichi Ohe

  DOI：10.1002/anie.201602241

  日期：2016.6.13

  A phosphine‐free iridium‐catalyzed reaction of isoxazol‐5(4H)‐ones (isoxazolones) has been developed, and affords 2H‐azirines through decarboxylation and ring contraction. This method provides an efficient and environmentally benign protocol which could replace the conventional approaches used to synthesize 2H‐azirines.

  现已开发出无膦的铱催化的异恶唑5（4 H）-酮（异恶唑酮）反应，并通过脱羧和环收缩反应生成2 H-叠氮基。该方法提供了一种高效且对环境无害的方案，可以代替用于合成2 H嗪的常规方法。
• 4, 5-dihydropyrazole-5-thione derivatives and miticides comprising the
  申请人：Otsuka Kagaku Kabushiki Kaisha

  公开号：US05639776A1

  公开（公告）日：1997-06-17

  The object of the present invention is to provide a novel 4, 5-dihydropyrazole-5-thione derivative which exerts remarkably potent miticidal activity. The 4, 5-dihydropyrazole-5-thione derivative of the present invention is represented by the general formula ##STR1## wherein R.sup.1 represents a straight- or branched-chain alkyl group having 1 to 12 carbon atoms or the like; R.sup.2 and R.sup.3 represent a lower alkyl group or the like; X represents a halogen atom or the like, n is 0 or an integer of 1 to 3; and A represents .paren open-st.C.paren close-st. or .paren open-st.N.paren close-st..

  本发明的目的是提供一种新颖的4,5-二氢吡唑-5-硫酮衍生物，具有显著的杀螨活性。本发明的4,5-二氢吡唑-5-硫酮衍生物由下述一般式表示： 其中R.sup.1表示具有1至12个碳原子的直链或支链烷基基团或类似物；R.sup.2和R.sup.3表示较低的烷基基团或类似物；X表示卤素原子或类似物，n为0或1至3的整数；A表示 .paren open-st.C.paren close-st. 或 .paren open-st.N.paren close-st.。
• 4,5-DIHYDROPYRAZOLE-5-THIONE DERIVATIVES AND ACARICIDE CONTAINING THE SAME
  申请人：OTSUKA KAGAKU KABUSHIKI KAISHA

  公开号：EP0751130A1

  公开（公告）日：1997-01-02

  The object of the present invention is to provide a novel 4, 5-dihydropyrazole-5-thione derivative which exerts remarkably potent miticidal activity. The 4, 5-dihydropyrazole-5-thione derivative of the present invention is represented by the general formula wherein R1 represents a straight- or branched-chain alkyl group having 1 to 12 carbon atoms or the like; R2 and R3 represent a lower alkyl group or the like; X represents a halogen atom or the like, n is 0 or an integer of 1 to 3; and A represents (̵C or (̵N.

  本发明的目的是提供一种新型的 4，5-二氢吡唑-5-硫酮衍生物，它具有显著的杀丝虫活性。本发明的 4，5-二氢吡唑-5-硫酮衍生物由通式表示 其中 R1 代表具有 1 至 12 个碳原子的直链或支链烷基或类似物；R2 和 R3 代表低级烷基或类似物；X 代表卤素原子或类似物；n 为 0 或 1 至 3 的整数；以及 A 代表 (̵C 或 (̵N.
• Radical N-heterocyclic carbene catalysis for β-ketocarbonyl synthesis
  作者：Takuya Ishii、Kazunori Nagao、Hirohisa Ohmiya

  DOI：10.1016/j.tet.2021.132212

  日期：2021.7
• Synthesis and Structure-Activity Relationships of Miticidal 4,5-Dihydropyrazole-5-thiones
  作者：Isao Tada、Minoru Motoki、Nobuyoshi Takahashi、Tetsuji Miyata、Tomoko Takechi、Toshiro Uchida、Yasushi Takagi

  DOI：10.1002/(sici)1096-9063(199610)48:2<165::aid-ps455>3.0.co;2-z

  日期：1996.10

  A series of novel 4,5-dihydropyrazole-5-thiones (DHPs) was synthesised by treating the corresponding dihydropyrazolones with Lawesson's reagent and evaluated for miticidal activity against two-spotted spider mites (Tetranychus urticae Koch). Of these, 3-(4-chlorophenyl)-4,4-dimethyl-1-phenyl-4, 5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-4-ethyl-4-methyl-1-phenyl-4,5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-1-phenyl-4,5-dihydropyrazole-5-thione-4-spirocyclopentane and 4,4-dimethyl-1-phenyl-3-(4-trifluoromethyl-phenyl)-4,5-dihydropyrazole-5-thione were highly active (pEC(50) > 4 . 0) and were more effective than the miticide dicofol (pEC(50) = 3 . 879), which has traditionally been used for the control of phytophagous mites. Structure-activity relationship (SAR) studies were performed on each position of the pyrazole ring of DHPs. The results indicated that the unsubstituted phenyl, 4-substituted phenyl and thioxo groups on the 1-, 3- and 5-positions of DHPs respectively were required for activity. Quantitative SAR studies using physicochemical parameters of substituents and the capacity factor k' as a hydrophobicity index suggested that: (a) the activities of all types of DHPs examined were mainly dominated by hydrophobicity, (b) the bulkiness of 4-substituents of the 3-phenyl ring favoured the activity and (c) the log k' optimum for all DHPs was 1 . 675, equivalent to a log P-ow value of c. 5 . 0.