(4-氯苯基)(氧代)乙酰氯 | 104132-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-氯苯基)(氧代)乙酰氯
• 英文名称: 2-(4-chlorophenyl)-2-oxoacetyl chloride
• 英文别名: p-chlorophenyl-2-oxoacetyl chloride；p-chlorophenylglyoxyl chloride；4-chlorophenylglyoxyl chloride；4-Chloro-alpha-oxo-benzeneacetyl chloride
• CAS: 104132-79-8
• 化学式: C₈H₄Cl₂O₂
• 分子量: 203.025
• InChiKey: JTXJZMXFVCMTKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  (4-氯苯基)(氧代)乙酰氯 在 chiral vanadium(V) sodium tetrahydroborate 、 氧气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 80.0h， 生成 (R)-S-t-butyl (4-chlorophenyl)-hydroxythioacetate
  参考文献：
  名称：

  Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives by C₄-Symmetric, Vanadate-Centered, Tetrakisvanadyl(V) Clusters Derived from N-Salicylidene-α-aminocarboxylates

  摘要：

  A series of chiral vanadyl(V) methoxides bearing 3-t-butyl-5-substituted N-salicylene-L-valinate and L-t-leucinate as chiral auxiliaries has been prepared. In all cases except the 3,5-di-t-butyl analogue, they exist as monomers both in solution and in the single crystal state. In the case of the 3,5-di-t-butyl analogue, the architectural nature of the vanadyl(V) complex highly depends on the base used during the complex formation event. A pentanuclear C-4-symmetric complex was formed when potassium salts were employed instead of the corresponding sodium salts. A central vanadate(V) unit serves to grip four identical chiral monomeric vanadyl(V) units together, by which a potassium ion sits on top of the four flanking units through carbonyl coordinations and serves to hold the whole cluster by cooperation with the central vanadate(V) unit. In comparison with the corresponding monomeric vanadyl(V) methoxide complex, the cluster complex was utilized to facilitate the asymmetric aerobic oxidations of various racemic alpha-hydroxyesters, -amides, and -thioesters with excellent selectivity factors (k(rel) 40 to >500).

  DOI：

  10.1021/jo070575f
• 作为产物：
  描述：

  (4-氯苯基)乙醛酸 在 草酰氯 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 (4-氯苯基)(氧代)乙酰氯
  参考文献：
  名称：

  N-杂环碳烯催化的炔基1,2-二酮

  摘要：

  首次通过N杂环卡宾（NHC）催化实现炔基1,2-二酮的酯化反应，从而可以在非常温和的条件下快速获得多种合成和药学上重要的α-吡喃酮。提出了一种全新的NHC催化的mpolung模式，其中包含O-酰化的烯丙基酯作为关键中间体。此外，据推测，以一系列的基团迁移和新的键形成为特征的空前反应路径证明了产物的形成。

  DOI：

  10.1002/adsc.201700700

文献信息

• PHENYLPYRIDINE COMPOUND AND BACTERICIDAL COMPOSITION CONTAINING THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1541557A1

  公开（公告）日：2005-06-15

  A phenylpyridine compound represented by the formula has an excellent controlling activity against plant diseases: [, wherein, in the formula, R1, R2, R3, R4 and R5 independently represent a hydrogen atom, a halogen atom and the like; R6 represents a hydrogen atom or a C1-C3 alkyl group; R7, R8 and R11 independently represent a hydrogen atom, a halogen atom and the like; R9 and R10 independently represent a hydroxyl group and the like; W1―W2=W3 ―W4 represents N―CH=CH―CH and the like; X represents an oxygen atom and the like; and Q represents a (C1-C6 alkoxy)methylene and the like].

  该式代表的苯基吡啶化合物对植物病害具有优异的控制活性: [其中，在该式中，R1、R2、R3、R4和R5分别代表氢原子、卤原子等; R6代表氢原子或C1-C3烷基; R7、R8和R11分别代表氢原子、卤原子等; R9和R10分别代表羟基等; W1―W2=W3―W4代表N―CH=CH―CH等; X代表氧原子等; Q代表(C1-C6烷氧基)亚甲基等]。
• Non‐Bonding 1,4‐Sulphur‐Oxygen Interaction Governs the Reactivity of α‐Ketothioesters in Triphenylphosphine‐Catalyzed Cyclization with Acetylenedicarboxylates
  作者：Abhijit Bankura、Jayanta Saha、Rajib Maity、Indrajit Das

  DOI：10.1002/adsc.202001376

  日期：2021.2.16

  1,4‐interaction involving C−S σ* orbital on the sulphur atom and the lone pair of electrons in the electron‐donating oxygen atom. This is apparent from the X‐ray crystallographically determined internuclear distance between the sulphur and ketone (C=O) oxygen atoms (2.71–2.85 Å), which is significantly less than the sum of their van der Waals radii (3.25–3.30 Å). The substitution on the S atom is oriented

  α-酮硫酯经过三苯基膦（PPh 3）与乙二酮酸酯的催化环化反应平稳，而α-酮氧酸酯则需要更苛刻的条件和有限的底物范围。该反应可与各种α-酮硫代酯很好地结合，以中等至极好的收率提供高度官能化的α，β-不饱和γ-丁内酯。硫酯衍生物的较高反应性似乎是由于有利的分子内非键合静电1,4-相互作用，涉及硫原子上的Cσσ*轨道和给电子氧原子中的孤对电子。从X射线晶体学确定的硫和酮（C = O）氧原子之间的核间距离（2.71-2.85Å）可以明显看出，该距离明显小于其范德华半径的总和（3.25-3.30Å） 。S原子上的取代沿直径方向远离酮O原子，以使它们之间的相互作用最大化。γ-丁内酯产品中S与呋喃O原子（2.70Å）之间的1,4-S⋅⋅⋅O接触也可以看到这种趋势。
• Nucleophilic β-Carbon Activation of Propionic Acid as a 3-Carbon Synthon by Carbene Organocatalysis
  作者：Zhichao Jin、Ke Jiang、Zhenqian Fu、Jaume Torres、Pengcheng Zheng、Song Yang、Bao-An Song、Yonggui Robin Chi

  DOI：10.1002/chem.201501481

  日期：2015.6.22

  Direct β‐carbon activation of propionic acid (C2H5CO2H) by carbene organocatalysis has been developed. This activation affords the smallest azolium homoenolate intermediate (without any substituent) as a 3‐carbon nucleophile for enantioselective reactions. Propionic acid is an excellent raw material because it is cheap, stable, and safe. This approach provides a much better solution to azolium homoenolate

  已经开发了通过卡宾有机催化作用对丙酸（C 2 H 5 CO 2 H）进行直接β-碳活化。这种活化提供了最小的均氮唑鎓中间体（无任何取代基），作为对映选择性反应的3碳亲核试剂。丙酸是便宜，稳定和安全的原料，因此是一种极好的原料。这种方法比以前建立的丙烯醛（没有任何取代基的烯醛）使用昂贵，不稳定且有毒的方法提供了更好的解决方案，用于合成均氮唑鎓。
• Asymmetric Friedel–Crafts Alkylation of α-Substituted β-Nitroacrylates: Access to β^2,2-Amino Acids Bearing Indolic All-Carbon Quaternary Stereocenters
  作者：Jian-Quan Weng、Qiao-Man Deng、Liang Wu、Kai Xu、Hao Wu、Ren-Rong Liu、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1021/ol403480v

  日期：2014.2.7

  A highly enantioselective Friedel–Crafts alkylation reaction of indoles with acyclic α-substituted β-nitroacrylates is developed under the catalysis of Ni(ClO4)2–bisoxazoline complex at 1 mol % catalyst loading, affording chiral indolic β-nitroesters bearing all-carbon quaternary stereocenters in excellent yields and ees of up to 97%. Transformation of one of the products to β2,2-amino ester and t

  在Ni（ClO 4）2-双恶唑啉配合物的催化下，以1 mol％的负载量催化吲哚与非环状α-取代的β-硝基丙烯酸酯的高度对映选择性Friedel-Crafts烷基化反应，从而得到具有全碳的手性吲哚β-硝基酯四元立体中心，产率极高，ee高达97％。举例说明了其中一种产物通过硝基还原和连续的Pictet-Spengler环化反应转变为β2,2-氨基酯和四氢-β-咔啉。
• Enantio- and chemoselective Brønsted-acid/Mg(ⁿBu)₂ catalysed reduction of α-keto esters with catecholborane
  作者：Dieter Enders、Bianca A. Stöckel、Andreas Rembiak

  DOI：10.1039/c4cc00427b

  日期：——

  The first enantio- and chemoselective Bronsted-acid catalysed reduction of alpha-keto esters with catecholborane has been developed. The alpha-hydroxy esters were obtained under mild reaction conditions in virtually quantitative yields and excellent enantioselectivities. With slight modifications both enantiomers can be obtained without any loss of selectivity.

  已开发出第一对映体和化学选择性布朗斯台德酸催化的儿茶酚硼烷还原α-酮酯。α-羟基酯是在温和的反应条件下以实际上定量的产率和优异的对映选择性而获得的。稍作修饰，即可得到两种对映体，而不会损失任何选择性。