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ethyl 2-(4-chlorophenyl)acrylate | 101492-44-8

中文名称
——
中文别名
——
英文名称
ethyl 2-(4-chlorophenyl)acrylate
英文别名
Benzeneacetic acid, 4-chloro-alpha-methylene-, ethyl ester;ethyl 2-(4-chlorophenyl)prop-2-enoate
ethyl 2-(4-chlorophenyl)acrylate化学式
CAS
101492-44-8
化学式
C11H11ClO2
mdl
——
分子量
210.66
InChiKey
LPWDPZHTBYYJTG-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

物化性质

  • 沸点:
    311.4±25.0 °C(Predicted)
  • 密度:
    1.146±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.3
  • 重原子数:
    14
  • 可旋转键数:
    4
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.18
  • 拓扑面积:
    26.3
  • 氢给体数:
    0
  • 氢受体数:
    2

SDS

SDS:40aa25fc559a8ee441cdc6ffaeda91cf
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    ethyl 2-(4-chlorophenyl)acrylate 盐酸氢气苄基三甲基氢氧化铵 作用下, 以 甲醇乙醇 为溶剂, 25.0~70.0 ℃ 、12.41 MPa 条件下, 反应 13.0h, 生成 2-(4-氯苯基)-4-氨基丁酸
    参考文献:
    名称:
    Metabolism of 3-(p-chlorophenyl)pyrrolidine. Structural effects in conversion of a prototype .gamma.-aminobutyric acid prodrug to lactam and .gamma.-aminobutyric acid type metabolites
    摘要:
    By use of rat liver or brain homogenate supernatants containing microsomes and/or mitochondria, it was found that the prototype GABAergic prodrug [3-(p-chlorophenyl)pyrrolidine (1)] underwent a series of alpha-oxidation transformations to a pair of amino acid metabolites and a pair of lactam metabolites [4-amino-3-(p-chlorophenyl)butanoic acid, baclofen (5); 4-amino-2-(p-chlorophenyl)butanoic acid (10); 4-(chlorophenyl)pyrrolidin-2-one and 3-(p-chlorophenyl)pyrrolidine-2-one (11)]. With the liver homogenates, the formation of the lactam metabolites was approximately 2 orders of magnitude greater than that of the amino acid metabolites, while with the brain homogenates, the amino acid and lactam pathways were of similar magnitude. For either tissue, for both the lactam and the amino acid series, attack at the less sterically hindered 5-position of the pyrrolidine ring was greater than the attack at the 2-position (5 greater than 10 and 6 greater than 11) with the exception of the liver homogenate mitochondrial fraction (6 less than 11). The parenteral administration of the prodrug 1 was found to give detectable brain levels of 5 as well as activity in an isoniazid-induced (GABA-inhibited) convulsion model.
    DOI:
    10.1021/jm00126a033
  • 作为产物:
    描述:
    参考文献:
    名称:
    缺电子烯烃的导向基团辅助的铜催化烯烃三氟甲基化
    摘要:
    提供的协助:标题反应中的引导基团不仅激活底物,而且还允许顺式三氟甲基化产物的立体定向形成。该反应操作简单并耐受多种官能团的,从而提供了β-CF的立体选择性合成的有效方法,3 -官能化的丙烯酰胺衍生物。
    DOI:
    10.1002/anie.201307245
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文献信息

  • Ester‐Directed Selective Olefination of Acrylates by Rhodium Catalysis
    作者:Ruokun Feng、Wenlong Yu、Kai Wang、Zhanxiang Liu、Yuhong Zhang
    DOI:10.1002/adsc.201300944
    日期:2014.5.5
    Esterdirected olefination of acrylates via rhodium(III)‐catalysis was developed. Various alkenes were reacted with acrylates to give the desired products in high stereoselectivity. Mechanistic investigations revealed that esterdirected CH bond activation was the key step to this reaction.
    开发了通过(III)催化的丙烯酸酯的酯基烯烃。使各种烯烃与丙烯酸酯反应,以高立体选择性得到所需产物。机理研究表明,酯导向的CH键活化是该反应的关键步骤。
  • Discovery of novel akt1 inhibitor induces autophagy associated death in hepatocellular carcinoma cells
    作者:Meng Yu、Minghui Zeng、Zhaoping Pan、Fengbo Wu、Li Guo、Gu He
    DOI:10.1016/j.ejmech.2020.112076
    日期:2020.3
    derivatives were designed, synthesized and evaluated as novel AKT1 inhibitors. In vitro antitumor assay results showed that compounds 9d-g and 9i potently suppressed the enzymatic activities of AKT1 and potently inhibited the proliferation of HepG2, Hep3B, Huh-7 and SMMC-7721 cancer cell lines. Among these derivatives, the compound 9f demonstrated the best inhibitory activities on AKT1 (IC50 = 0.034 μM)
    在这项研究中,设计,合成和评估了一系列噻吩并[2,3-d]嘧啶生物,并将其作为新型AKT1抑制剂进行了评估。体外抗肿瘤测定结果表明,化合物9d-g和9i有效抑制AKT1的酶活性,并有效抑制HepG2,Hep3B,Huh-7和SMMC-7721癌细胞系的增殖。在这些衍生物中,化合物9f对AKT1(IC50 = 0.034μM)和Huh-7细胞(IC50 = 0.076μM)表现出最佳的抑制活性。一组生物学实验表明,化合物9f通过Akt / mTOR信号通路介导的自噬机制抑制了Huh-7的细胞增殖。此外,在皮下Huh-7异种移植模型中验证了9f的抗肿瘤能力。一起,
  • Hydrazone derivatives, process for producing same, insecticides and/or
    申请人:Sumitomo Chemical Co., Ltd.
    公开号:US05451607A1
    公开(公告)日:1995-09-19
    There are disclosed hydrazone derivatives of the general formula [I]: ##STR1## wherein R.sup.1 is halogen, etc.; R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; R.sup.3 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; R.sup.4 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; R.sup.5 is C.sub.1 -C.sub.6 alkyl, etc.; R.sup.6 is hydrogen or C.sub.1 -C.sub.6 alkyl, etc.; A is (CH.sub.2).sub.t, O, S(O).sub.n, etc.; a is an integer of 1 to 4; n is an integer of 0 to 2; and t is an integer of 1 to 3; as well as production processes therefor, insecticides and/or acaricides containing the same as an active ingredient and intermediate compounds thereof.
    已公开的一般式[I]的腙衍生物如下:##STR1## 其中R.sup.1是卤素等;R.sup.2是氢或C.sub.1 -C.sub.6烷基等;R.sup.3是氢或C.sub.1 -C.sub.6烷基等;R.sup.4是氢或C.sub.1 -C.sub.6烷基等;R.sup.5是C.sub.1 -C.sub.6烷基等;R.sup.6是氢或C.sub.1 -C.sub.6烷基等;A是(CH.sub.2).sub.t,O,S(O).sub.n等;a是1到4的整数;n是0到2的整数;t是1到3的整数;以及生产过程,含有其作为活性成分的杀虫剂和/或杀螨剂以及中间体化合物。
  • Enantioselective Enolate Protonation in Sulfa–Michael Addition to α-Substituted <i>N</i>-Acryloyloxazolidin-2-ones with Bifunctional Organocatalyst
    作者:Nirmal K. Rana、Vinod K. Singh
    DOI:10.1021/ol202808n
    日期:2011.12.16
    Organocatalytic conjugate addition of thiols to α-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically
    鸡纳生物碱衍生的硫脲的存在下,已经研究了醇向α-取代的N-丙烯酰基恶唑丁二酮的有机催化共轭加成反应,然后进行不对称质子化。使用假对映异构体奎宁/奎尼丁衍生的催化剂,两种对映体都可以以相同平的对映体选择性获得。加成/质子化产物已转化为有用的生物活性分子。
  • Rhodium(<scp>iii</scp>)-catalyzed C–H allylation of electron-deficient alkenes with allyl acetates
    作者:Chao Feng、Daming Feng、Teck-Peng Loh
    DOI:10.1039/c4cc07597h
    日期:——

    Rhodium-catalyzed C–H allylation of acrylamide derivatives with various allyl acetates was reported. The use of weakly coordinating directing group resulted in high reaction efficiency and excellent γ-selectivity. This reaction displays broad functional group tolerance, which opens a new synthetic pathway for the access of functionalized 1,4-diene skeletons.

    催化的C-H烯丙基化反应报道了使用各种烯丙醋酸酯丙烯酰胺衍生物进行反应。使用弱配位导向基团导致高反应效率和优异的γ-选择性。该反应显示出广泛的官能团容忍性,为获得官能化的1,4-二烯骨架开辟了新的合成途径。
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同类化合物

(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S,S)-邻甲苯基-DIPAMP (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(-)-4,12-双(二苯基膦基)[2.2]对环芳烷(1,5环辛二烯)铑(I)四氟硼酸盐 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(4-叔丁基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(3-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-4,7-双(3,5-二-叔丁基苯基)膦基-7“-[(吡啶-2-基甲基)氨基]-2,2”,3,3'-四氢1,1'-螺二茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (R)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4S,4''S)-2,2''-亚环戊基双[4,5-二氢-4-(苯甲基)恶唑] (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (3aR,6aS)-5-氧代六氢环戊基[c]吡咯-2(1H)-羧酸酯 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[((1S,2S)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1S,2S,3R,5R)-2-(苄氧基)甲基-6-氧杂双环[3.1.0]己-3-醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (1-(2,6-二氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙蒿油 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫-d6 龙胆紫