ethyl-2-chloro-3-(4-methoxyphenyl)-3-oxopropanoate | 24045-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl-2-chloro-3-(4-methoxyphenyl)-3-oxopropanoate
• 英文别名: Ethyl I+/--chloro-4-methoxy-I(2)-oxobenzenepropanoate；ethyl 2-chloro-3-(4-methoxyphenyl)-3-oxopropanoate
• CAS: 24045-74-7
• 化学式: C₁₂H₁₃ClO₄
• 分子量: 256.686
• InChiKey: XPIOOKLIVZDNER-UHFFFAOYSA-N

物化性质

• 沸点：
  356.2±27.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl-2-chloro-3-(4-methoxyphenyl)-3-oxopropanoate 在 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 ethyl 2-acetoxy-3-(4-methoxyphenyl)-3-(4-methoxyphenylamino)acrylate
  参考文献：
  名称：

  α-羟基β-氨基酸衍生物的高度非对映选择性和对映选择性合成：路易斯碱催化的α-乙酰氧基β-烯氨基酯的氢化硅烷化反应

  摘要：

  通过设计：合成了一系列α-乙酰氧基-β-烯氨基酯1，然后进行催化不对称氢化硅烷化。在手性路易斯碱催化剂的存在下，反应顺利进行，以高收率提供了多种手性α-乙酰氧基β-氨基酸衍生物，具有良好的非对映选择性和对映选择性。

  DOI：

  10.1002/anie.201102150
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 磺酰氯 、 sodium hydride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 ethyl-2-chloro-3-(4-methoxyphenyl)-3-oxopropanoate
  参考文献：
  名称：

  α-羟基β-氨基酸衍生物的高度非对映选择性和对映选择性合成：路易斯碱催化的α-乙酰氧基β-烯氨基酯的氢化硅烷化反应

  摘要：

  通过设计：合成了一系列α-乙酰氧基-β-烯氨基酯1，然后进行催化不对称氢化硅烷化。在手性路易斯碱催化剂的存在下，反应顺利进行，以高收率提供了多种手性α-乙酰氧基β-氨基酸衍生物，具有良好的非对映选择性和对映选择性。

  DOI：

  10.1002/anie.201102150

文献信息

• HETEROCYCLIC COMPOUND AND p27Kip1 DEGRADATION INHIBITOR
  申请人：Uchida Hiroshi

  公开号：US20130079306A1

  公开（公告）日：2013-03-28

  A novel heterocyclic compound or a salt thereof useful for selectively inhibiting the degradation of p27 Kip1 is provided. The compound or the salt thereof is represented by the following formula (1): wherein A represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, the group A may have a substituent; the ring B represents a 5- to 8-membered monocyclic heterocyclic ring or a condensed ring containing the monocyclic heterocyclic ring, the ring B may have a substituent; the ring C represents an aromatic ring, the ring C may have a substituent; L represents a linker comprising a main chain having 3 to 5 atoms selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom, wherein at least one atom in the main chain is a hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, the linker L may have a substituent; and n is 0 or 1.

  提供了一种新型杂环化合物或其盐，用于选择性地抑制p27Kip1的降解。该化合物或其盐由以下式（1）表示：其中A代表烷基、环烷基、芳基或杂环基，基团A可能有取代基；环B代表5至8成员的单环杂环环或包含该单环杂环环的缩合环，环B可能有取代基；环C代表芳香环，环C可能有取代基；L代表包含3至5个原子的主链的连接物，所述原子选自碳原子、氮原子、氧原子和硫原子组成的群，其中主链中的至少一个原子是选自氮原子、氧原子和硫原子组成的杂原子，连接物L可能有取代基；n为0或1。
• Electrochemical chlorination and bromination of electron-deficient C H bonds in quinones, coumarins, quinoxalines and 1,3-diketones
  作者：Dan Yu、Ruixue Ji、Zhihui Sun、Wenjie Li、Zhong-Quan Liu

  DOI：10.1016/j.tetlet.2021.153514

  日期：2021.12

  The electrochemistry-promoted chlorination and bromination of electron-deficient CH bonds was developed, using quinones, coumarins, quinoxalines and 1,3-diketones. This protocol features readily available and safe halogen sources (hydrochloric acid and KBr), high site-selectivity and mild reaction conditions. It could provide an efficient access to a series of chlorinated and brominated quinones, coumarins

  使用醌、香豆素、喹喔啉和 1,3-二酮，开发了电化学促进的缺电子 CH键的氯化和溴化。该协议具有易于获得且安全的卤素源（盐酸和 KBr）、高位点选择性和温和的反应条件。它可以有效地获取一系列氯化和溴化醌、香豆素、喹喔啉和 1,3-二酮。
• p-substituted benzene sulphonamides
  申请人：GEIGY CHEM CORP

  公开号：US02858318A1

  公开（公告）日：1958-10-28

  The invention comprises p-substituted benzenesulphonamides of the general formula: <;FORM:0846573/IV(b)/1>; (wherein R1 represents hydrogen or an alkyl, alkoxyalkyl, carboxy, carbalkoxy, cycloalkyl, aralkyl, aryl, hydroaryl, furyl, thienyl or thienylalkyl radical), and any aromatic ring in R1 may be substituted by halogen atoms or alkyl, alkoxy, alkylenedioxy, carboxy or carbalkoxy groups, R2 represents hydrogen or an alkyl, aralkyl or dialkylaminoalkyl radical and X represents oxygen, NH or NR2, or X-R2 represents a morpholino radical, and n is O or 1, and the preparation thereof by condensing p-thiocarbamylbenzenesulphonamide of the formula :- <;FORM:0846573/IV(b)/2>; with a compound of the general formula:- <;FORM:0846573/IV(b)/3>; (wherein Hal represents chlorine or bromine), and thereafter, if desired, converting to carboxy groups by hydrolysis and/or oxidation any substituents so convertible, and, if desired, converting carboxy groups by the action of inorganic halides into halogenocarboxyl groups and reacting these, or carbalkoxy groups, with compounds of the general formula : H-X-R2 (IV). The compounds (I), which are useful as oral diuretics, can also be prepared by : (a) replacing compound (III) by a derivative of a halogenomalonic dialdehyde (e.g. a -bromo-b :b -diethoxypropionaldehyde) and oxidizing the resulting 2-(p-sulphamylphenyl)-thiazole-2-aldehyde; (b) reacting p-substituted benzenesulphonic acid derivatives of the general formula: <;FORM:0846573/IV(b)/4>; (wherein Y represents chlorine, bromine or an aryloxy group, R111 represents R1 or a halogenocarbonyl group and R4 represents -CO-X-R2 or a halogenocarbonyl group) with the amount of ammonia corresponding to the number of groups present capable of reacting therewith: or (c) oxidizing sulphenamides of the general formula:- <;FORM:0846573/IV(b)/5>; p-Substituted benzenesulphochlorides of general formula V (Y=Cl) are prepared by oxidizing chlorination of p-(5-carboxythiazolyl-2)-phenyl benzyl sulphides or of bis-p-(5-carboxythiazolyl-2) -phenyl disulphides or their esters, or by reducing a p-(5-carboxythiazolyl-2)-nitrobenzene to the amino compound, converting this into its diazonium chloride, and treating the latter with SO2 in a non-aqueous solution, or in an aqueous solution with subsequent conversion of the resulting sulphinic acid into the corresponding sulphochloride. p-Substituted benzenesulphenamides of general formula VI are prepared by the action of alkali metal hypochlorites in the presence of ammonia on p-(5-carboxythiazolyl-2)-phenyl benzyl sulphides, bis-p-(5-carboxythiazobyl-2)-phenyl disulphides or 2-(p-mercaptophenyl)-thiazole-5-carboxylic acids obtained therefrom by reduction, or on esters of any of these acids.

  该发明涉及一般式为p-取代苯磺酰胺的化合物：（其中R1代表氢或烷基，烷氧基烷基，羧基，羰基烷氧基，环烷基，芳基烷基，芳基，烷基芳基，呋喃基，噻吩基或噻吩基烷基基团），R1中的任何芳环可以被卤素原子或烷基，烷氧基，烷二氧基，羧基或羰基烷基团取代，R2代表氢或烷基，芳基烷基或二烷基氨基烷基基团，X代表氧，NH或NR2，或X-R2代表吗啉基团，n为O或1，其制备方法通过将一般式为p-硫代氨基苯磺酰胺的化合物与一般式为的化合物进行缩合；然后，如有必要，通过水解和/或氧化将可转化的取代基转化为羧基，并如有必要，通过无机卤化物的作用将羧基转化为卤代羧基，并将这些羧基或羰基与的化合物反应。这些化合物（I）可用作口服利尿剂，也可通过以下方法制备：（a）用卤代丙二醛衍生物（例如-溴-b：b-二乙氧基丙醛）替换化合物（III）并氧化生成的2-(p-磺胺基苯基)-噻唑-2-醛；（b）将一般式为的p-取代苯磺酸衍生物（其中Y代表氯，溴或芳氧基，R111代表R1或卤代羰基，R4代表-CO-X-R2或卤代羰基）与相应的氨量反应；或（c）将一般式为的硫代胺类氧化为p-取代苯磺酰氯类化合物V（Y=Cl）通过氧化氯化p-(5-羧基噻唑基-2)-苯基苄硫醚或双-p-(5-羧基噻唑基-2)-苯基二硫化物或它们的酯制备，或通过将p-(5-羧基噻唑基-2)-硝基苯还原为氨基化合物，将其转化为重氮盐，然后在无水溶液中或在含SO2的水溶液中处理后，将所得的亚磺酸转化为相应的磺酰氯。通过在p-(5-羧基噻唑基-2)-苯基苄硫醚，双-p-(5-羧基噻唑基-2)-苯基二硫化物或通过还原得到的2-(p-巯基苯基)-噻唑-5-羧酸酯上的碱金属次氯酸盐作用，或在任何这些酸的酯上作用。
• Asymmetric Reduction of 2-Chloro-3-oxo Esters by Transfer Hydrogenation
  作者：Jinjin Bai、Shifeng Miao、Yun Wu、Yawen Zhang

  DOI：10.1002/cjoc.201180419

  日期：2011.11

  Asymmetric reduction of 2‐chloro‐3‐oxo esters was achieved by catalytic transfer hydrogenation using [RuCl2(p‐cymene)](S,S)‐TsDPEN as the chiral catalyst and HCOOH‐Et3N as the hydrogen source. Moderate to good yields (up to 85%) and good enantioselectivities (up to 98% ee) were obtained.

  通过使用[RuCl 2（p- cymene）]（S，S）-TsDPEN作为手性催化剂和HCOOH-Et 3 N作为氢源进行催化转移氢化，可以实现2-氯-3-氧代酸酯的不对称还原。获得了中等至良好的产率（高达85％）和良好的对映选择性（高达98％ee）。
• Enantioselective ruthenium-mediated hydrogenation: developments and applications
  作者：Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt

  DOI：10.1016/s0022-328x(98)00680-9

  日期：1998.9

  A general preparation of chiral ruthenium(II) catalysts and the homogeneous enantioselective hydrogenation of prochiral olefins and keto groups are presented. Some applications to the synthesis of biologically active compounds are reported. (C) 1998 Elsevier Science S.A. All rights reserved.