2-(2-methoxyphenyl)-2-oxoacetyl chloride | 1011297-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-methoxyphenyl)-2-oxoacetyl chloride
• CAS: 1011297-70-3
• 化学式: C₉H₇ClO₃
• 分子量: 198.606
• InChiKey: FCTHOHSAKJHDNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-methoxyphenyl)-2-oxoacetyl chloride 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.0h， 生成 1-(2-methoxyphenyl)-3-phenylprop-2-yn-1-one
  参考文献：
  名称：

  产生苯并吡喃酮和苯并呋喃的新气相多米诺工艺

  摘要：

  一种通过气相热解含有 2-甲氧基苯基的 β,γ-二氧磷叶立德来制备黄酮的新多米诺骨牌方法因中间体黄酮-3-基自由基的意外和新颖的脱羰反应而受挫，导致 2-苯基苯并呋喃。基于二氧戊环保护一个羰基或选择性消除 β,β'-二氧代或 β-氧代-β'-硫代叶立德的替代方法并不成功，但 β-氧代-β'-苯基亚氨基叶立德的热解确实给出了所需的多米诺骨牌反应导致中等收率的受保护的苯并吡喃酮。

  DOI：

  10.3987/com-15-s(t)14
• 作为产物：
  描述：

  2-(2-methoxyphenyl)-2-oxoacetic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-methoxyphenyl)-2-oxoacetyl chloride
  参考文献：
  名称：

  通过Pd催化的芳基卤化物分子内亲核加成反应到α-酮酰胺中，合成3-羟基羟吲哚。

  摘要：

  在nBuOH和碱的存在下，Pd / PtBu（3）催化的卤代芳基分子内亲核加成到α-酮酰胺中的产率很高，提供了一种新的，直接的，有效的合成策略来获得3-羟基羟吲哚。

  DOI：

  10.1039/b917958e

文献信息

• 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。
• Nickel‐Catalyzed Intramolecular Nucleophilic Addition of Aryl or Vinyl Chlorides to α‐Ketoamides Through CCl Bond Activation
  作者：Jin‐Xiu Hu、Hao Wu、Chuan‐Ying Li、Wei‐Jian Sheng、Yi‐Xia Jia、Jian‐Rong Gao

  DOI：10.1002/chem.201100256

  日期：2011.5.2

  Nickeleophilic addition! The first example of a nickel‐catalyzed direct intramolecular nucleophilic addition of aryl or vinyl chlorides to α‐ketoamides through CCl bond activation is reported, which takes place under mild reaction conditions (see scheme).

  亲尼性加成！到C镍-催化的直接分子内的亲核加成芳基或乙烯基氯化物，以α酮酰胺的的第一示例 Cl键激活报道，这需要温和的反应条件下进行（见方案）。
• The Photochemical Synthesis of N-arylacetyl Lactams
  作者：Lei Jiang、Nan Ma、Jun Qiu、Ronghua Zhang

  DOI：10.3184/174751913x13594855388300

  日期：2013.3

  The photochemical formation is described of N-arylacetyl lactams from the corresponding N-phenylglyoxylic acid derivatives of pyrrolidine and piperidine-2-carboxylic acids in an acetone:water mixture containing potassium carbonate. Evidence is presented for the possible formation and cleavage of a cyclic ether during this process which leads to the 1, 4-transfer of a carbonyl group.

  描述了在含有碳酸钾的丙酮：水混合物中，由吡咯烷和哌啶-2-羧酸的相应 N-苯基乙醛酸衍生物光化学生成 N-芳基乙酰内酰胺的过程。有证据表明，在这一过程中可能会形成和裂解环醚，从而导致羰基的 1，4-转移。
• A Facile Pathway to Enantiomerically Enriched 3-Hydroxy-2-Oxindoles: Asymmetric Intramolecular Arylation of α-Keto Amides Catalyzed by a Palladium-DifluorPhos Complex
  作者：Liang Yin、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1002/anie.201102158

  日期：2011.8.8

  Less metal wastes: The first catalytic, enantioselective intramolecular aryl‐transfer reaction of aryl triflates to ketones has been developed (see scheme; R1=R2=aromatic and aliphatic). This method features overall practicality, including substrate stability and accessibility (protecting‐group free) plus no need for the use of stoichiometric amounts of metals.

  减少金属废料：已开发出芳基三氟甲磺酸酯向酮的第一个催化，对映选择性分子内芳​​基转移反应（参见方案； R 1 = R 2 =芳族和脂族）。该方法具有整体实用性，包括基材稳定性和可及性（无保护基团），而且无需使用化学计量的金属。
• Asymmetric Aerobic Oxidation of α-Hydroxy Acid Derivatives by <i>C</i>₄-Symmetric, Vanadate-Centered, Tetrakisvanadyl(V) Clusters Derived from <i>N</i>-Salicylidene-α-aminocarboxylates
  作者：Chien-Tien Chen、Sampada Bettigeri、Shiue-Shien Weng、Vijay D. Pawar、Ya-Hui Lin、Cheng-Yuan Liu、Way-Zen Lee

  DOI：10.1021/jo070575f

  日期：2007.10.1

  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).