3-(4-chlorophenyl)-2,2-dimethylpropanoic acid chloride | 63293-86-7

• 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: 3-(4-chlorophenyl)-2,2-dimethylpropanoic acid chloride
• 英文别名: 3-(4-chlorophenyl)-2,2-dimethylpropionyl chloride；3-(4-Chlorophenyl)-2,2-dimethylpropanoyl chloride
• CAS: 63293-86-7
• 化学式: C₁₁H₁₂Cl₂O
• 分子量: 231.122
• InChiKey: HOISPJLGAWRCIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-2,2-dimethylpropanoic acid chloride 在 十二羰基三钌 、 乙烯 、 水 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 160.0 ℃ 、1.72 MPa 条件下， 反应 120.0h， 生成 3-(4-chlorobenzyl)-3-methyl-1-(pyridin-2-ylmethyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Highly Regioselective Carbonylation of Unactivated C(sp³)–H Bonds by Ruthenium Carbonyl

  摘要：

  The regioselective carbonylation of unactivated C(sp(3))-H bonds of aliphatic amides was achieved using Ru-3(CO)(12) as a catalyst. The presence of a 2-pyridinylmethylamine moiety in the amide is crucial for a successful reaction. The reaction shows a preference for C-H bonds of methyl groups as opposed to methylene C-H bonds and tolerates a variety of functional groups. The stoichiometric reaction of an amide with Ru-3(CO)(12) gave a dinuclear ruthenium complex in which the 2-pyridinylmethylamino moiety was coordinated to the ruthenium center in an N,N manner.

  DOI：

  10.1021/ja2001709
• 作为产物：
  描述：

  4-氯苄溴 在 正丁基锂 、 氯化亚砜 、 水 、 二异丙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 20.0h， 生成 3-(4-chlorophenyl)-2,2-dimethylpropanoic acid chloride
  参考文献：
  名称：

  Highly Regioselective Carbonylation of Unactivated C(sp³)–H Bonds by Ruthenium Carbonyl

  摘要：

  The regioselective carbonylation of unactivated C(sp(3))-H bonds of aliphatic amides was achieved using Ru-3(CO)(12) as a catalyst. The presence of a 2-pyridinylmethylamine moiety in the amide is crucial for a successful reaction. The reaction shows a preference for C-H bonds of methyl groups as opposed to methylene C-H bonds and tolerates a variety of functional groups. The stoichiometric reaction of an amide with Ru-3(CO)(12) gave a dinuclear ruthenium complex in which the 2-pyridinylmethylamino moiety was coordinated to the ruthenium center in an N,N manner.

  DOI：

  10.1021/ja2001709

文献信息

• Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst
  作者：Jitan Zhang、Hui Chen、Cong Lin、Zhanxiang Liu、Chen Wang、Yuhong Zhang

  DOI：10.1021/jacs.5b07424

  日期：2015.10.14

  A new method of cobalt-catalyzed synthesis of pyrrolidinones from aliphatic amides and terminal alkynes was discovered through a C-H bond functionalization process on unactivated sp(3) carbons with the silver cocatalyst using a bidentate auxiliary. For the first time, a broad range of easily accessible alkynes are exploited as the reaction partner in C(sp(3))-H bond activation to give the important

  通过使用双齿助剂的银助催化剂对未活化的 sp(3) 碳进行 CH 键功能化过程，发现了一种钴催化合成吡咯烷酮从脂肪族酰胺和末端炔烃的新方法。第一次，广泛的易于获得的炔烃被用作 C(sp(3))-H 键活化的反应伙伴，以位点选择性方式提供重要的 5-亚乙基-吡咯烷-2-酮。该反应耐受多种官能团，包括 -F、-Cl、-Br、-CF3、醚、环丙烷和噻吩。吡啶配体和芳香族溶剂都对促进反应性起着重要作用。这种钴催化的环化反应可以成功地扩展到各种芳香酰胺，以提供各种异吲哚啉酮。
• Phenoxyalkylcarboxylic acid compounds and serum-lipid and triglyceride
  申请人：Boehringer Mannheim GmbH

  公开号：US04151303A1

  公开（公告）日：1979-04-24

  Novel phenoxyalkylcarboxylic acid compounds of the formula ##STR1## wherein A is aryl, aryloxy, substituted aryl or substituted aryloxy, wherein the substituents are selected from lower alkyl, lower alkoxy, halogen and haloalkyl; B is a straight-chained or branched, saturated or unsaturated hydrocarbyl containing up to 5 carbon atoms; N is 1, 2 or 3 and R.sub.1, r.sub.2 and R.sub.3, which may be the same or different, are hydrogen or lower alkyl; And the pharmacologically compatible salts thereof; have been found to be outstandingly effective in depressing serum-lipid and triglycerides in the serum of mammals.

  新颖的苯氧烷基羧酸化合物的化学式为##STR1##其中A是芳基、芳氧基、取代芳基或取代芳氧基，其中取代基选择自较低的烷基、较低的烷氧基、卤素和卤代烷基；B是直链或支链、饱和或不饱和的含有最多5个碳原子的烃基；N为1、2或3，R.sub.1、r.sub.2和R.sub.3，可以相同也可以不同，为氢或较低的烷基；以及其药理相容盐；已被发现在抑制哺乳动物血清脂质和甘油三酯方面具有显著的有效性。
• Synthesis of γ-Lactams via Pd(II)-Catalyzed C(sp³)–H Olefination Using a Self-Cleaving Polyfluoroethylsulfinyl Directing Group
  作者：Nan-Qi Shao、Yu-Hao Chen、Chen Li、Dong-Hui Wang

  DOI：10.1021/acs.orglett.0c00326

  日期：2020.9.18

  A monodentate directing group, 2-chlorotetrafluoroethylsulfinylmide (-NHSOCF2CF2Cl), for inert C(sp3)–H bond activation is reported. This directing group shows efficient ability in Pd(II)-catalyzed C(sp3)–H olefination. The desired olefination products undergo subsequent Michael addition and in situ expulsion of the auxiliary to provide the free NH γ-lactam products. Preliminary mechanistic studies

  据报道，用于惰性C（sp 3）-H键活化的单齿导向基团2-氯四氟乙基亚磺酰亚胺（-NHSOCF 2 CF 2 Cl）。该指导基团在Pd（II）催化的C（sp 3）–H烯化反应中显示出有效的能力。所需的烯烃化产物随后进行迈克尔加成反应并就地排出助剂以提供游离的NHγ-内酰胺产物。初步的机理研究表明，辅助基团对于C（sp 3）–H激活至关重要。
• Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp3) H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams
  作者：Danni Zhou、Chunxia Wang、Mingliang Li、Zheng Long、Jingbo Lan

  DOI：10.1016/j.cclet.2017.06.007

  日期：2018.1

  The direct Pd-catalyzed beta-C(sp(3))-H activation and cyclization of aliphatic amides bearing a removable 2-pyridylmethyl directing group with gem-dibromoolefins is described for the first time to construct a variety of gamma-lactams. The resulting products with Z- and E-configurations can be easily separated and purified after the reaction, demonstrating the effectiveness and applicability of the method herein developed. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Remote C–H bond functionalization reveals the distance-dependent isotope effect
  作者：Jiao-Jie Li、Ramesh Giri、Jin-Quan Yu

  DOI：10.1016/j.tet.2008.03.026

  日期：2008.7

  Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage. (C) 2008 Elsevier Ltd. All rights reserved.