ethyl 4-chloro-4-phenylbutanoate | 2125-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-chloro-4-phenylbutanoate
• 英文别名: 4-Chlor-4-phenyl-buttersaeure-ethylester
• CAS: 2125-35-1
• 化学式: C₁₂H₁₅ClO₂
• 分子量: 226.703
• InChiKey: MKYGEUMQVDEKGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4-chloro-4-phenylbutanoate 在 水 、 3,6-bis(triphenylphosphonium)cyclohexene peroxodisulfate 作用下， 以 乙腈 为溶剂， 反应 0.4h， 以81%的产率得到4-氧代-4-苯基丁酸乙酯
  参考文献：
  名称：

  用 3,6-双（三苯基鏻）环己烯过二硫酸盐选择性氧化苄基底物为其相应的羰基化合物

  摘要：

  摘要 3,6-双(三苯基鏻)环己烯过二硫酸盐 (BTPCP) 被发现是一种高效且选择性的氧化剂，可在温和和中性条件下将苄基一卤化物、腈和胺转化为其相应的羰基化合物。

  DOI：

  10.1081/scc-120018692
• 作为产物：
  描述：

  苯 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 8.75h， 生成 ethyl 4-chloro-4-phenylbutanoate
  参考文献：
  名称：

  Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity

  摘要：

  A series of phenoxybutanoic acid derivatives were synthesized and tested for their antagonistic activity on the contraction of the rat thoracic aortic ring induced by endothelin-1. Preliminary screening results showed that 6e and 6g with benzoheterocycles demonstrated significant antagonistic activities when compared to the reference compound BQ123. The results from additional assays for the binding affinity and selectivity for endothelin receptors showed that 6e was a selective ETA antagonist with a nanomolar IC50. Moreover, 6e was effective in relieving hypoxia-induced pulmonary arterial hypertension and right ventricular weight ratio. Therefore, 6e may have potential for further development as a therapeutic agent for the treatment of cardiovascular diseases. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.003

文献信息

• Carbon-carbon bond-forming reactions of zinc homoenolate of esters. A novel three-carbon nucleophile with general synthetic utility
  作者：Eiichi Nakamura、Satoshi Aoki、Kouichi Sekiya、Hiroji Oshino、Isao Kuwajima

  DOI：10.1021/ja00260a018

  日期：1987.12

  Reactions d'addition sur les composes carbonyles, allylation, arylation, vinylation et acylation en presence ou non de catalyseurs

  反应 d'addition sur les 组成羰基、烯丙基化、芳基化、乙烯基化和酰化在非脱催化剂的存在下
• Atom transfer radical addition (ATRA) of carbon tetrachloride and chlorinated esters to various olefins catalyzed by Cp′Ru(PPh3)(PR3)Cl complexes
  作者：Radhika P. Nair、Jocelyn A. Pineda-Lanorio、Brian J. Frost

  DOI：10.1016/j.ica.2011.11.008

  日期：2012.1

  addition of CCl 4 to internal olefins. The activity of Cp ∗ Ru(PTA)(PPh 3 )Cl and Cp ∗ Ru(PTA)(PMe 3 )Cl were comparable to that of the highly efficient ATRA catalyst, Cp ∗ Ru(PPh 3 ) 2 Cl. The addition of CCl 3 CO 2 Et to styrene catalyzed by Cp′Ru(PPh 3 )(PR 3 )Cl (Cp′ = Dp, Ind, Cp, Tp) are also reported here. Two new compounds, 3-chloro-3-phenyl-2-(trichloromethyl)-1-phenylpropan-1-one and 1,3,3,3-tetrachloro-1

  使用Cp ∗ Ru（PPh 3）（PR 3）Cl络合物，其中PR 3 = PMe 3，PPh 3或PTA（PTA = 1,3,5-triaza-7-phosphaadamantanetan）催化原子转移自由基向苯乙烯中添加氯化酯（CCl 3 CO 2 Et，CH 2 ClCO 2 Et），以及向各种烯烃添加CCl 4。单加合物以中等至优异的产率获得。此外，获得高选择性以将CCl 4加到内烯烃中。Cp * Ru（PTA）（PPh 3）Cl和Cp * Ru（PTA）（PMe 3）Cl的活性与高效ATRA催化剂Cp * Ru（PPh 3）2 Cl的活性相当。在此还报道了通过Cp'Ru（PPh 3）（PR 3）Cl（Cp'= Dp，Ind，Cp，Tp）催化将CCl 3 CO 2 Et加到苯乙烯中。两种新化合物3-氯-3-苯基-2-（三氯甲基）-1-苯基丙烷-1-酮和1,3,3,3-四氯-1,2-二苯基丙烷
• Exploring the Substrate Scope of the Ru(II)-Catalyzed Kharasch Reaction
  作者：Eskender Mume、Ian J. Munslow、Klas Källström、Pher G. Andersson

  DOI：10.1135/cccc20071005

  日期：——

  The Kharasch reaction, or atom-transfer addition of polyhalogenated alkanes to alkenes is known to be catalyzed by a number of Ru(II) complexes. The easily prepared [RuCl₂(PPh₃)₃] was used to investigate the reaction scope. A number of halogenated alkanes were added to a range of alkenes with good to excellent regioselectivities.

  Kharasch反应，或者说卤代烷烃与烯烃的原子转移加成反应，已知可以由多种Ru(II)配合物催化。易于制备的[RuCl₂(PPh₃)₃]被用来研究反应的范围。许多卤代烷烃被加到一系列烯烃中，具有良好到优秀的区域选择性。
• Substituted phenyl compounds
  申请人：Rhone-Poulenc Rorer Limited

  公开号：US06211234B1

  公开（公告）日：2001-04-03

  Compounds of formula (I) are described wherein R1 is hydrogen, -(lower alkyl)q(CO2R6 or OH), —CN, —C(R7)═NOR8, NO2, —O(lower alkyl)R9, —C≡C—R10, —CR11═C(R12)(R13), —C(═O)CH2C(═O)CO2H, —CO(R14), alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, thiocarbamoyl, substituted carbamoyl, substituted thiocarbamoyl, sulphamoyl or an optionally substituted nitrogen-containing ring, m, n, o and p are independently zero or 1 and R2, R3, R4 and R5 are various groups; and physiologically acceptable salts, N-oxides and prodrugs thereof. The compounds have endothelin antagonist activity and are useful as pharmaceuticals.

  式(I)的化合物描述如下，其中R1为氢，-(较低烷基)q(CO2R6或OH)，—CN，—C(R7)HNOR8，NO2，—O(较低烷基)R9，—C≡C—R10，—CR11CH(R12)(R13)，—C(O)CH2C(O)CO2H，—CO(R14)，烷基硫醚，烷基亚砜基，烷基磺酰基，氨基甲酰基，硫代氨基甲酰基，取代的氨基甲酰基，取代的硫代氨基甲酰基，磺酰胺基或可选择取代的含氮环，m、n、o和p独立地为零或1，R2、R3、R4和R5为各种基团；以及其生理学上可接受的盐、N-氧化物和前药。这些化合物具有内皮素拮抗活性，并可用作药物。
• Trichlorotitanium and alkoxytitanium homoenolates. Preparation, characterization, and utilization for organic synthesis
  作者：Eiichi. Nakamura、Hiroji. Oshino、Isao. Kuwajima

  DOI：10.1021/ja00273a032

  日期：1986.6

  demi-equivalent d'alcoolate de titane (IV) sont plus reactives que I, fournissant des voies d'acces a des hydroxy-4 esters, γ-lactones et cyclopropanecarboxylates. Discussion du mecanisme de formation des homoenolates

  Des eseses alcoxytitaniumgenerees par traitement de trichlorotitanio-3propionates d'alkyles (I) avec un demi-equivalent d'alcoolate de titane (IV) sont plus reactors que I, Fournissant des voies d'acces a des hydroxy-4esters, γ-内酯和环丙烷羧酸盐。同烯醇化物形成机制的讨论