ethyl 5-(p-chlorophenyl)-3-oxovalerate | 74631-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(p-chlorophenyl)-3-oxovalerate
• 英文别名: ethyl 5-(4-chlorophenyl)-3-oxopentanoate
• CAS: 74631-92-8
• 化学式: C₁₃H₁₅ClO₃
• 分子量: 254.713
• InChiKey: IZCPRMFNASOKEA-UHFFFAOYSA-N

物化性质

• 沸点：
  159-162 °C(Press: 0.6 Torr)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 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：

  ethyl 5-(p-chlorophenyl)-3-oxovalerate 在 氢氧化钾 、 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.25h， 生成 5-(4-chloro-benzyl)-1-ethyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid
  参考文献：
  名称：

  化学治疗的研究I. 5-取代-4-氧代-1,4-二氢-3-吡啶羧酸衍生物的合成

  摘要：

  通过使1,3,5-三嗪与4-取代的乙酰乙酸乙酯衍生物在乙醇钠存在下反应，来合成5-取代的4-氧代-1，4-二氢-3-吡啶甲酸乙酯。通过N-烷基化（用磷酸三乙酯或烷基卤化物）和吡啶酮酯的碱水解制备抗微生物研究所需的1-烷基-5-取代-4-氧代-1，4-二氢-3-吡啶羧酸。

  DOI：

  10.1002/jhet.5570170229
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-氯氯苄 在 sodium hydride 、 正丁基锂 作用下， 以 四氢呋喃 、 mineral oil 、 正己烷 为溶剂， 以70%的产率得到ethyl 5-(p-chlorophenyl)-3-oxovalerate
  参考文献：
  名称：

  Oxaziridine-Mediated Intramolecular Amination of sp³-Hybridized C−H Bonds

  摘要：

  We describe a new oxaziridine-mediated approach to the amination of sp(3)-hybridized C-H bonds. In the presence of a copper(II) catalyst, N-sulfonyl oxaziridines participate in efficient intramolecular cyclization reactions to afford a variety of piperidine and tetrahydroisoquinoline structures. The aminal intermediates provide a convenient functional handle for further elaboration of these structures, demonstrating the utility of this new methodology for the rapid construction of structurally complex nitrogen-containing heterocycles.

  DOI：

  10.1021/ja906183g

文献信息

• Formation of Two 4-Imidazolylmethylphosphonium Salts and their Synthetic Studies Toward Histamine H₃-Ligands
  作者：Takushi Kurihara、Shinya Harusawa、Makoto Kawamura、Shuji Koyabu、Tomoko Hosokawa、Lisa Araki、Yasuhiko Sakamoto、Takeshi Hashimoto、Yumiko Yamamoto、Atsushi Yamatodani

  DOI：10.1055/s-2003-42442

  日期：——

  A simple and convenient preparation of [1H-imidazol-4(5)-yl]methyl}triphenylphosphonium chloride (5) is described. The phosphonium salt 5 could be applied to the synthesis of 1-[1H-imidazol-4(5)-yl]-5-arylpentan- or 6-arylhexan-3-ones 4a-d exhibiting histamine H3-antagonistic activities via a 1,3-diazafulvene intermediate 6 generated from 5. Further, two-methylene-enlongated homolog 3 of imifuramine was efficiently synthesized, starting from Wittig olefination of aldehyde 24 using [(1-tritylimidazol-4-yl)methyl]triphenylphosphonium chloride 7.

  本文描述了一种简单方便的[1H-咪唑-4(5)-基]甲基}三苯基氯化鏻（5）的制备方法。鏻盐 5 可用于通过由 5 生成的 1,3-二氮杂富烯中间体 6 合成 1-[1H-咪唑-4(5)-基]-5-芳基戊烷或 6-芳基己-3-酮 4a-d，这些化合物具有组胺 H3 拮抗活性。此外，还利用[(1-三苯甲基咪唑-4-基)甲基]三苯基氯化鏻 7 从醛 24 的 Wittig 烯化反应开始，高效合成了亚氨基呋喃的二亚甲基延长同系物 3。
• METHOD FOR PRODUCING CARBOXYLIC ACID COMPOUND
  申请人：Kowa Company, Ltd.

  公开号：EP2003112A1

  公开（公告）日：2008-12-17

  A method for conveniently preparing 2,2-dichloro-12-(4-chlorophenyl)-10-hydroxydodecanoic acid useful as an active ingredient of therapeutic agents for diseases such as diabetes at a high yield, which comprises the step of reacting a compound represented by the following general formula (A): wherein X represents a halogen atom, and a compound represented by the following general formula (B): CHCl2COOR1 wherein R1 represents hydrogen atom or a protective group of carboxyl group, to prepare a compound represented by the following general formula (C): wherein R1 has the same meaning as that defined above.

  一种方便地制备2,2-二氯-12-(4-氯苯基)-10-羟基十二烷酸的方法，该方法可用于治疗糖尿病等疾病的治疗剂，且产率高，包括以下步骤：将下列通式(A)所表示的化合物与下列通式(B)所表示的化合物反应，其中X代表卤素原子，R1代表氢原子或羧基的保护基，以制备下列通式(C)所表示的化合物，其中R1的含义与上述相同。
• METHOD FOR PREPARING CARBOXYLIC ACID COMPOUND
  申请人：Katsurada Manabu

  公开号：US20100261933A1

  公开（公告）日：2010-10-14

  A method for conveniently preparing 2,2-dichloro-12-(4-chlorophenyl)-10-hydroxydodecanoic acid useful as an active ingredient of therapeutic agents for diseases such as diabetes at a high yield, which comprises the step of reacting a compound represented by the following general formula (A): wherein X represents a halogen atom, and a compound represented by the following general formula (B): CHCl 2 COOR 1 wherein R 1 represents hydrogen atom or a protective group of carboxyl group, to prepare a compound represented by the following general formula (C): wherein R 1 has the same meaning as that defined above.

  一种制备2,2-二氯-12-(4-氯苯基)-10-羟基十二酸的方法，该化合物可用作治疗糖尿病等疾病的活性成分，且得率高。该方法包括将下述通式（A）所代表的化合物（其中X代表卤素原子）与下述通式（B）所代表的化合物（其中R1代表氢原子或羧基的保护基）反应，以制备下述通式（C）所代表的化合物（其中R1具有与上述定义相同的含义）。
• Structural Optimization and Biological Evaluation of 2-Substituted 5-Hydroxyindole-3-carboxylates as Potent Inhibitors of Human 5-Lipoxygenase
  作者：Eva-Maria Karg、Susann Luderer、Carlo Pergola、Ulrike Bühring、Antonietta Rossi、Hinnak Northoff、Lidia Sautebin、Reinhard Troschütz、Oliver Werz

  DOI：10.1021/jm900212y

  日期：2009.6.11

  Pharmacological suppression of leukotriene biosynthesis by inhibitors of 5-lipoxygenase (5-LO) is a strategy to intervene with inflammatory and allergic disorders. We recently presented 2-amino-5-hydroxy-1H-indoles as efficient 5-LO inhibitors in cell-based and cell-free assays. Structural optimization led to novel benzo[g]indole-3-carboxylates exemplified by ethyl 2-(3-chlorobenzyl)-5-hydroxy-1H-benzo[g]indole-3-carboxylate (compound 11a), which inhibits 5-LO activity in human neutrophils and recombinant human 5-LO with IC50 values of 0.23 and 0.086 mu M, respectively. Notably, 11a efficiently blocks 5-LO product formation in human whole blood assays (IC50 = 0.83-1.6 mu M) and significantly prevented leukotriene B-4 production in pleural exudates of carrageenan-treated rats, associated with reduced severity of pleurisy. Together, on the basis of their high potency against 5-LO and the marked efficacy in biological systems, these novel and straightforward benzo[g]indole-3-carboxylates may have potential as anti-inflammatory therapeutics.
• BALOGH M.; HERMECZ I.; MESZAROS Z.; SIMON K.; PUSZTAY L.; HORVATH G.; DVO+, J. HETEROCYCL. CHEM., 1980, 17, NO 2, 359-368
  作者：BALOGH M.、 HERMECZ I.、 MESZAROS Z.、 SIMON K.、 PUSZTAY L.、 HORVATH G.、 DVO+

  DOI：——

  日期：——