2-(2-chlorobenzylidene)acetoacetic acid ethyl ester | 15725-22-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(2-chlorobenzylidene)acetoacetic acid ethyl ester
• 英文别名: ethyl 2-chlorobenzylideneacetoacetate；2-acetyl-3-(2-chloro-phenyl)-acrylic acid ethyl ester；2-Acetyl-3-(2-chlor-phenyl)-acrylsaeure-aethylester；ethyl 2-acetyl-3-(2-chlorophenyl)acrylate；ethyl-2-(2-chlorobenzyliden)acetoacetate；2-(2-Chlor-benzyliden)-acetessigsaeure-aethylester；Ethyl 2-(2-chlorobenzylidene)acetoacetate；ethyl 2-[(2-chlorophenyl)methylidene]-3-oxobutanoate
• CAS: 15725-22-1
• 化学式: C₁₃H₁₃ClO₃
• 分子量: 252.697
• InChiKey: QXQWIOZONGXWQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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-(2-chlorobenzylidene)acetoacetic acid ethyl ester 在 ammonium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 5-amino-4-(2-chlorphenyl)-2,7,7-trimethyl-1,4,6,7,8,9-hexahydrobenzo[b][1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  六氢苯并萘啶类光学活性化合物及其药物用途

  摘要：

  本发明公开了六氢苯并萘啶类光学活性化合物及其药物用途，该化合物为左旋(S)-5-氨基-4-(2-氯苯基)-2,7,7-三甲基-1,4,6,7,8,9-六氢苯并[b][1,8]萘啶-3-羧酸乙酯，它具有T1结构，或其药学上可接受的盐。本发明还公开了该光学异构体的组合物及其应用。本发明中的化合物T1相较其右旋体化合物T2及消旋体化合物T，表现出了更强的乙酰胆碱酯酶活性和钙通道抑制活性，更优异的药物吸收代谢性质，综合表现出了很强的体内药效结果。

  公开号：

  CN105481851A
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-氯苯甲醛 在 哌啶 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 2-(2-chlorobenzylidene)acetoacetic acid ethyl ester
  参考文献：
  名称：

  一系列新型的1,5-苯并噻唑啉衍生物作为潜在的抗菌剂的合成和生物学评价

  摘要：

  有效地合成了两个系列的新型1,5-苯并硫氮杂pine衍生物（23个化合物），并评估了其抗菌和抗真菌活性。结果表明，该化合物对被测微生物具有广谱的活性，并且与细菌相比，对真菌的活性更高。化合物2e表现出最大的抗菌活性。对结构-活性关系的初步研究表明，苯环中的取代基对这些化合物的抗菌活性有很大影响。

  DOI：

  10.1016/j.ejmech.2008.12.021

文献信息

• Novel 2-Amino-1,4-dihydropyridine Calcium Antagonists. I. Synthesis and Antihypertensive Effects of 2-Amino-1,4-dihydropyridine Derivatives Having Nitroxyalkoxycarbonyl Groups at 3- and/or 5-Position.
  作者：Takashi KOBAYASHI、Teruhiko INOUE、Zyunichiro KITA、Haruo YOSHIYA、Shigeyoshi NISHINO、Kiyoshi OIZUMI、Tomio KIMURA

  DOI：10.1248/cpb.43.788

  日期：——

  Novel 2-amino-1,4-dihydropyridine derivatives, which contain nitroxy-alkoxycarbonyl groups at the 3- and/or 5-position, were synthesized and their pharmaceutical effect was evaluated in spontaneously hypertensive rats. The structure-activity relationships are discussed in terms of potency, onset-rapidity, and duration of antihypertensive activity. Remarkably prolonged duration of antihypertensive action

  合成了新型的2-氨基-1,4-二氢吡啶衍生物，该衍生物在3-位和/或5-位含有硝基氧基-烷氧基羰基，并在自发性高血压大鼠中评估了它们的药理作用。从效价，起效迅速和降压活性持续时间方面讨论了构效关系。当在酯链的任一侧引入叔氨基时，观察到抗高血压作用的持续时间显着延长。
• Synthesis and biological evaluation of a novel series of 1,5-benzothiazepine derivatives as potential antimicrobial agents
  作者：Lanzhi Wang、Ping Zhang、Xuemei Zhang、Yonghong Zhang、Yuan Li、Yongxiang Wang

  DOI：10.1016/j.ejmech.2008.12.021

  日期：2009.7

  Two series of novel 1,5-benzothiazepine derivatives (23 compounds) were efficiently synthesized and evaluated for antibacterial and antifungal activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fungi than bacteria. Compound 2e exhibited the greatest antimicrobial activity. Preliminary study

  有效地合成了两个系列的新型1,5-苯并硫氮杂pine衍生物（23个化合物），并评估了其抗菌和抗真菌活性。结果表明，该化合物对被测微生物具有广谱的活性，并且与细菌相比，对真菌的活性更高。化合物2e表现出最大的抗菌活性。对结构-活性关系的初步研究表明，苯环中的取代基对这些化合物的抗菌活性有很大影响。
• 1,4-DIHYDRO-NAPHTHYRIDINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION AND USE THEREOF
  申请人：Chen Rong

  公开号：US20140364443A1

  公开（公告）日：2014-12-11

  Disclosed are 1,4-dihydro-naphthyridine derivatives and pharmaceutical composition and uses thereof. The 1,4-dihydro-naphthyridine derivatives are a compound capable of inhibiting acetylcholinesterase activity and preventing extracellular calcium from flowing into a cell via a calcium channel, i.e., having a dual-activity, which are of potential importance as a pharmaceutical and can be used to prepare the drugs for treating cardiovascular diseases, cerebrovascular diseases and dementia.

  本文披露了1,4-二氢-萘啶衍生物及其药物组合物和用途。1,4-二氢-萘啶衍生物是一种能够抑制乙酰胆碱酯酶活性并通过钙通道阻止细胞外钙流入细胞的化合物，即具有双重活性，对于制备用于治疗心血管疾病、脑血管疾病和痴呆症的药物具有潜在重要性。
• Studies on dihydropyridines. II. Synthesis of 4,7-dihydropyrazolo(3,4-b)pyridines with vasodilating and antihypertensive activities.
  作者：IKUO ADACHI、TERUO YAMAMORI、YOSHIHARU HIRAMATSU、KATSUNORI SAKAI、HATSUO SATO、MASARU KAWAKAMI、OSAMU UNO、MOTOHIKO UEDA

  DOI：10.1248/cpb.35.3235

  日期：——

  A series of 4-aryl-4, 7-dihydropyrazolo [3, 4-b] pyridine-5-carboxylate derivatives (72-149) was prepared and the compounds were tested for Ca-blocking activity in isolated guinea pig portal vein, antihypertensive activity in spontaneously hypertensive rats, and coronary vasodilating effect in isolated guinea pig heart. A number of derivatives had potent antihypertensive and coronary vasodilating activities. The structure-activity relationships of the series indicated that a 3-cyclopentyl or 3-cyclohexyl substituent and a hydrophobic 5-ester moiety with moderate bulkiness were effective for increasing the pharmacological potencies.

  合成了一系列4-芳基-4, 7-二氢吡唑[3, 4-b]吡啶-5-羧酸酯衍生物（72-149），并对这些化合物进行了在分离的豚鼠门静脉中的钙通道阻滞活性、自发性高血压大鼠中的抗高血压活性以及在分离的豚鼠心脏中的冠状血管扩张作用的测试。多种衍生物具有强效的抗高血压和冠状血管扩张活性。该系列的结构-活性关系表明，3-环戊基或3-环己基取代基以及具有适度体积的疏水性5-酯基团对于提高药理活性是有效的。
• Rates of reaction of <i>n</i>-butanethiol with some conjugated heteroenoid compounds
  作者：C. E. Lough、D. J. Currie、H. L. Holmes

  DOI：10.1139/v68-127

  日期：1968.3.1

  The reactions of substituted 3-benzal-2,4-pentanediones, ethyl benzalacetoacetates, diethyl benzalmalonates, benzalmalonamides, cinnamalmalononitriles, β-nitrostyrenes, and β-nitropropenylbenzenes with excess n-butanethiol go essentially to completion in 20% aqueous ethanolic solution buffered to pH 7. The second order rate constants derived from the reactions of meta- and para- substituted derivatives correlate well with Hammett a constants. The nature and conformation of the functional group cis to the phenyl group determines the extent to which ortho substituents hinder the reaction.

  替代3-苯甲酮-2,4-戊二酮、乙基苯基乙酮酸酯、二乙基苯基丙二酸酯、苯基丙二酰胺、肉桂基丙烯腈、β-硝基苯乙烯和β-硝基丙烯基苯在过量正丁硫醇存在下在pH 7缓冲的20%乙醇水溶液中基本上完全反应。从间位和对位取代衍生物的反应中得出的二阶速率常数与Hammett a常数很好地相关。苯基团顺式于苯基团的功能团的性质和构象决定了邻位取代物对反应的阻碍程度。