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2-Chloroethyl 2-(2-cyanobenzylidene)acetoacetate | 75206-24-5

中文名称
——
中文别名
——
英文名称
2-Chloroethyl 2-(2-cyanobenzylidene)acetoacetate
英文别名
2-chloroethyl 2-[(2-cyanophenyl)methylidene]-3-oxobutanoate
2-Chloroethyl 2-(2-cyanobenzylidene)acetoacetate化学式
CAS
75206-24-5;75206-25-6
化学式
C14H12ClNO3
mdl
——
分子量
277.707
InChiKey
USPSQDSKRUMEHF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    19
  • 可旋转键数:
    6
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.21
  • 拓扑面积:
    67.2
  • 氢给体数:
    0
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    2-Chloroethyl 2-(2-cyanobenzylidene)acetoacetate三乙胺 作用下, 以 乙醇 为溶剂, 反应 59.0h, 生成 3-O-ethyl 5-O-[2-[(4-methoxyphenyl)methyl-methylamino]ethyl] 4-(2-cyanophenyl)-2-(diethoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate
    参考文献:
    名称:
    Studies on Nilvadipine. II. Synthesis and Structure-Activity Relationships of 2-Hydroxymethyl- and 2-Cyano-1,4-dihydropyridines Containing Heteroatom-Substituted Ester at the 5-Position.
    摘要:
    描述了新型2-羟甲基-和2-氰基-1, 4-二氢吡啶的合成,这些化合物在其核的5位上具有杂原子取代的烷基酯基团。酯的引入是通过以下方法之一进行的:经过改进的Hantzsch方法(方法A)、通过方法A获得的氯乙酸酯的水解(方法B)或用各种氨基取代氯原子(方法C)。2位的羟甲基和氰基团的制备与之前的文献相似。1)本文中制备的化合物的降压活性与之前报告的在5位的相应烷基酯进行了比较。发现N-苄基甲基氨基乙酯,特别是N-(4-氯苄基)-和N-(3, 4-二氯苄基)-N-甲基氨基乙酯,是1, 4-二氢吡啶核5位上合适的取代基,并且在一系列2-羟甲基-1, 4-二氢吡啶衍生物中,这些取代基的降压活性比简单的烷基酯略强。然而,在一系列2-氰基-1, 4-二氢吡啶衍生物中,效果则相反。两者均被发现不如已经在临床上用于治疗高血压的nilvadipine (1c)。
    DOI:
    10.1248/cpb.40.912
  • 作为产物:
    描述:
    参考文献:
    名称:
    Studies on Nilvadipine. II. Synthesis and Structure-Activity Relationships of 2-Hydroxymethyl- and 2-Cyano-1,4-dihydropyridines Containing Heteroatom-Substituted Ester at the 5-Position.
    摘要:
    描述了新型2-羟甲基-和2-氰基-1, 4-二氢吡啶的合成,这些化合物在其核的5位上具有杂原子取代的烷基酯基团。酯的引入是通过以下方法之一进行的:经过改进的Hantzsch方法(方法A)、通过方法A获得的氯乙酸酯的水解(方法B)或用各种氨基取代氯原子(方法C)。2位的羟甲基和氰基团的制备与之前的文献相似。1)本文中制备的化合物的降压活性与之前报告的在5位的相应烷基酯进行了比较。发现N-苄基甲基氨基乙酯,特别是N-(4-氯苄基)-和N-(3, 4-二氯苄基)-N-甲基氨基乙酯,是1, 4-二氢吡啶核5位上合适的取代基,并且在一系列2-羟甲基-1, 4-二氢吡啶衍生物中,这些取代基的降压活性比简单的烷基酯略强。然而,在一系列2-氰基-1, 4-二氢吡啶衍生物中,效果则相反。两者均被发现不如已经在临床上用于治疗高血压的nilvadipine (1c)。
    DOI:
    10.1248/cpb.40.912
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文献信息

  • Certain 4-aryl-1,4-dihydro-3,5-pyridinedicarboxylates having
    申请人:Fujisawa Pharmaceutical Co., Ltd.
    公开号:US04525478A1
    公开(公告)日:1985-06-25
    1,4-Dihydropyridine derivatives of the general formula ##STR1## having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.
    具有扩血管和降压活性的一般式为##STR1##的1,4-二氢吡啶衍生物,其制备方法以及用于治疗心血管疾病的制药组合物。
  • 1,4-Dihydropyridine derivatives, and pharmaceutical method of the same
    申请人:Fujisawa Pharmaceutical Co., Ltd.
    公开号:US04284634A1
    公开(公告)日:1981-08-18
    1,4-dihydropyridine derivatives of the general formula ##STR1## having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.
    具有扩血管和降压活性的1,4-二氢吡啶衍生物,其一般式为##STR1##,制备方法以及用于治疗心血管疾病的制药组合物。
  • 1,4-Dihydropyridine derivatives, pharmaceutical compositions containing
    申请人:Fujisawa Pharmaceutical Co., Ltd.
    公开号:US04338322A1
    公开(公告)日:1982-07-06
    This invention relates to 2-or 6-cyano or cyano(lower)alkyl-4-phenyl or (substituted phenyl)1,4-dihydropyridine-3,5-dicarboxylates and derivatives which have vasodilating and hypertensive activity, processes for their preparation, pharmaceutical compositions for containing same and for methods of treating hypertension and cardiovascular diseases.
    本发明涉及2-或6-氰基或氰基(较低)烷基-4-苯基或(取代苯基)1,4-二氢吡啶-3,5-二羧酸酯及其衍生物,其具有扩血管和降压活性,其制备方法,含有它们的制药组合物和治疗高血压和心血管疾病的方法。
  • 1,4-Dihydro-pyridine derivatives and methods of using same
    申请人:Fujisawa Pharmaceutical Co., Ltd.
    公开号:US04370334A1
    公开(公告)日:1983-01-25
    1,4-Dihydropyridine derivatives of the general formula ##STR1## having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.
    具有扩血管和降压活性的一般式为##STR1##的1,4-二氢吡啶衍生物,其制备过程以及用于治疗心血管疾病的药物组合物。
  • Studies on Nilvadipine. II. Synthesis and Structure-Activity Relationships of 2-Hydroxymethyl- and 2-Cyano-1,4-dihydropyridines Containing Heteroatom-Substituted Ester at the 5-Position.
    作者:Yoshinari SATOH、Masaharu ICHIHASHI、Kazuo OKUMURA
    DOI:10.1248/cpb.40.912
    日期:——
    The synthesis of new 2-hydroxymethyl- and 2-cyano-1, 4-dihydropyridines possessing a heteroatom-substituted alkyl ester group at the 5-position of the nucleus in described. The esters were introduced via a suitable method selected from the modified Hantzsch method (method A), the hydrolysis of a chloroethyl ester obtained by method A (method B) or the replacement of the chlorine atom with various kinds of amino groups (method C). Hydroxymethyl and cyano groups at the 2-position were prepared in a similar manner to that described in a previous papare.1)The hypotensive activities of the compounds prepared in this paper were compared with the corresponding alkyl ester at the 5-position reported previously. It was found that N-benzylmethylaminoethyl esters, especially N-(4-chlorobenzyl)-and N-(3, 4-dichlorobenzyl)-N-methylaminoethyl esters, were suitable substituents at the 5-position of the 1, 4-dihydropyridine nucleus and that these substituents were somewhat more effective for hypotensive activity than simple alkyl esters in a series of 2-hydroxymethyl-1, 4-dihydropyridine derivatives. But it was found that the effect was reversed in a series of 2-cyano-1, 4-dihydropyridine derivatives. Both of them were found to be inferior to nilvadipine (1c), accepted in clinical use for the treatment of hypertension.
    描述了新型2-羟甲基-和2-氰基-1, 4-二氢吡啶的合成,这些化合物在其核的5位上具有杂原子取代的烷基酯基团。酯的引入是通过以下方法之一进行的:经过改进的Hantzsch方法(方法A)、通过方法A获得的氯乙酸酯的水解(方法B)或用各种氨基取代氯原子(方法C)。2位的羟甲基和氰基团的制备与之前的文献相似。1)本文中制备的化合物的降压活性与之前报告的在5位的相应烷基酯进行了比较。发现N-苄基甲基氨基乙酯,特别是N-(4-氯苄基)-和N-(3, 4-二氯苄基)-N-甲基氨基乙酯,是1, 4-二氢吡啶核5位上合适的取代基,并且在一系列2-羟甲基-1, 4-二氢吡啶衍生物中,这些取代基的降压活性比简单的烷基酯略强。然而,在一系列2-氰基-1, 4-二氢吡啶衍生物中,效果则相反。两者均被发现不如已经在临床上用于治疗高血压的nilvadipine (1c)。
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