(2,4-dimethyl-phenyl)-acetyl chloride | 90705-86-5

• 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: (2,4-dimethyl-phenyl)-acetyl chloride
• 英文别名: 2-(2,4-Dimethylphenyl)acetyl chloride
• CAS: 90705-86-5
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: VHSRWRNGXYOGJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (2,4-dimethyl-phenyl)-acetyl chloride 在 4-二甲氨基吡啶 、 sodium azide 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 4-[1-(2,4-Dimethyl-benzylcarbamoyl)-3,3-diethyl-4-oxo-azetidin-2-yloxy]-benzoic acid
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  (2,4-苯二甲基)乙酸 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 (2,4-dimethyl-phenyl)-acetyl chloride
  参考文献：
  名称：

  Quinolones as gonadotropin releasing hormone (GnRH) antagonists: simultaneous optimization of the C(3)-aryl and C(6)-substituents

  摘要：

  A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to he optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00318-8

文献信息

• Discovery of novel tertiary amide derivatives as NEDDylation pathway activators to inhibit the tumor progression in vitro and in vivo
  作者：Dong-Jun Fu、Jian Song、Ting Zhu、Xiao-Jing Pang、Sheng-Hui Wang、Yan-Bing Zhang、Bo-Wen Wu、Jun-Wei Wang、Xiaolin Zi、Sai-Yang Zhang、Hong-Min Liu

  DOI：10.1016/j.ejmech.2020.112153

  日期：2020.4

  NAE1-Ubc12-Cullin1 NEDDylation via interacting with NAE1 directly. Furthermore, the activation of NEDDylation resulted in the degradation of inhibitor of apoptosis proteins (IAPs). Importantly, Ⅶ-31 inhibited tumor growth in xenograft models in vivo without the apparent toxicity. In summary, it is the first time to reveal that Ⅶ-31 deserves consideration for cancer therapy as a NEDDylation activator.

  NEDDylation通路调节多种生理过程，与抑制剂不同，NEDDylation激活剂很少被研究。合成了新的酰胺衍生物，并评估了其对MGC803，MCF-7和PC-3细胞的抗增殖活性。其中，Ⅶ-31对MGC803细胞表现出最强的活性，IC 50值为94 nmol / L。细胞机制阐明，Ⅶ-31通过针对MGC803细胞的内在和外在途径抑制细胞活力，使细胞周期停滞在G2 / M期并诱导凋亡。另外，Ⅶ-31通过直接与NAE1相互作用激活了NAE1-Ubc12-Cullin1 NEDDylation。此外，NEDDylation的激活导致凋亡蛋白（IAPs）抑制剂的降解。重要的是，Ⅶ-31抑制了体内异种移植模型中的肿瘤生长，而没有明显的毒性。总之，这是首次揭示the -31作为NEDDylation激活剂值得用于癌症治疗。
• Pd-Catalyzed Remote <i>Meta-</i>C–H Functionalization of Phenylacetic Acids Using a Pyridine Template
  作者：Zhong Jin、Ling Chu、Yan-Qiao Chen、Jin-Quan Yu

  DOI：10.1021/acs.orglett.7b03336

  日期：2018.1.19

  An effective pyridine based U-shaped template has been developed to enable a diverse range of meta-C–H functionalizations of phenylacetic acid scaffolds. This new template has extended the reaction scope to cross-coupling with ArBF3K as well as iodination using 1,3-diiodo-5,5-dimethylhydantoin as the iodination reagent.

  已开发出一种有效的基于吡啶的U形模板，可实现苯乙酸支架的多种间位-C–H官能化。该新模板将反应范围扩展到与ArBF 3 K交叉偶联以及使用1,3-二碘-5,5-二甲基乙内酰脲作为碘化试剂的碘化反应。
• Sulfonyl-containing 3,4-diaryl-3-pyrrolin-2-ones, preparation method, and medical use thereof
  申请人：Research Institute of Material Medica, Chinese Academy of Medical Sciences;

  公开号：US20040029951A1

  公开（公告）日：2004-02-12

  The invention relates to sulfonyl-containing 3,4-diaryl-3-pyrrolin-2-ones compounds having formula (I) 1 wherein R 1 is selected from the group consisting of 4-methylsulfonyl, 4-aminosulfonyl, hydrogen, 2-, 3-, or 4-halogen, C 1 -C 6 -alkyl, cyclopentyl, cyclohexyl, C 1 -C 4 -alkoxy, hydroxy, cyano, nitro, amino or trifluoromethyl; R 2 is selected from the group consisting of 4-methylsulfonyl, 4-aminosulfonyl, hydrogen, 2-, 3-, or 4-halogen, C1-C6-alkyl, cyclopentyl, cyclohexyl, C 1 -C 4 -alkoxy, hydroxy, cyano, nitro, amino or trifluoromethyl; and R 3 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, i-propyl, c-propyl, n-butyl, isobutyl; provided that when R 1 is a methylsulfonyl or aminosulfonyl group, R 2 is any group as defined above except a methylsulfonyl or aminosulfonyl group; and when R 2 is a methylsulfonyl or aminosulfonyl group, R 1 is any group as defined above except a methylsulfonyl or aminosulfonyl group, also to processes for the preparation of such compounds, to pharmaceutical compositions containing such compounds, and to the medical use of such compounds in the treatment of diseases relating to the inhibition of cyclooxygenase-2 (COX-2).

  该发明涉及具有以下结构的磺酰基含有的3,4-二芳基-3-吡咯烯-2-酮化合物，其化学式为（I）： 其中R1选自以下组：4-甲基磺酰基，4-氨基磺酰基，氢，2-，3-或4-卤素，C1-C6-烷基，环戊基，环己基，C1-C4-烷氧基，羟基，氰基，硝基，氨基或三氟甲基；R2选自以下组：4-甲基磺酰基，4-氨基磺酰基，氢，2-，3-或4-卤素，C1-C6-烷基，环戊基，环己基，C1-C4-烷氧基，羟基，氰基，硝基，氨基或三氟甲基；R3选自以下组：氢，甲基，乙基，正丙基，异丙基，仲丙基，正丁基，异丁基；但当R1为甲基磺酰基或氨基磺酰基时，R2为上述定义之外的任何基团；当R2为甲基磺酰基或氨基磺酰基时，R1为上述定义之外的任何基团。同时，该发明还涉及制备这类化合物的方法，含有这类化合物的药物组合物，以及这类化合物在治疗与环氧合酶-2（COX-2）抑制相关的疾病中的医学用途。
• Palladium-Catalyzed Remote <i>meta</i>-C–H Bond Deuteration of Arenes Using a Pyridine Template
  作者：Hui Xu、Min Liu、Ling-Jun Li、Ya-Fang Cao、Jin-Quan Yu、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.9b01784

  日期：2019.6.21

  deuteration of a series of substrates, including phenylacetic acids, hydrocinnamic acid, benzylphosphonate, benzylsulfonate, and benzyl and phenyl ethyl alcohol ester, is developed by using a pyridine-based directing template. The template is installed into the substrate through a practical ester linkage. Under mild reaction conditions, a variety of phenylacetic acids containing alkyl, methoxyl, and halo substituents

  钯催化的一系列底物的间选择性CH氘化反应是通过使用吡啶基导向模板开发的，这些底物包括苯乙酸，氢肉桂酸，苄基膦酸酯，苄基磺酸酯以及苄基和苯基乙醇酯。通过实用的酯键将模板安装到基材中。在温和的反应条件下，各种含有烷基，甲氧基和卤素取代基的苯乙酸在反应中是相容的，导致在间位高水平的D掺入。
• Quinoline derivatives, their production and use as ACAT inhibitors
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05362742A1

  公开（公告）日：1994-11-08

  A quinoline derivative of the formula (I): ##STR1## wherein each phenyl ring of A and B can have one or more substituents; X is ##STR2## (R.sup.1 is a hydrogen atom, a lower alkyl group or a lower alkoxy group) or ##STR3## (R.sup.2 is a hydrogen atom or a lower alkyl group); Y is --(CH.sub.2).sub.m --(m is 0, 1 or 2) or --CH.dbd.CH--, Z is a group of the formula: ##STR4## wherein each phenyl ring of C and D can have one or more substituents, R.sup.3 and R.sup.4 are each a hydrogen or halogen atom, or a lower alkyl, lower alkoxy, lower acyloxy, lower alkoxycarbonyloxy, N,N-di-lower alkylcarbamoyloxy, optionally esterified carboxy or hydroxyl group, R.sup.5 is a halogen atom, or a lower alkyl, lower alkoxy, lower acyloxy, lower alkoxycarbonyloxy, N,N-di-lower alkylcarbamoyloxy, optionally esterified carboxy or hydroxyl group, R.sup.6 and R.sup.7 are each a hydrogen atom or a lower alkyl group, and n, o and p are each 1 or 2; l is 0 or 1; or its salt, which is useful as a drug for atherosclerosis.

  化合物I的喹啉衍生物：##STR1## 其中A和B的每个苯环可以有一个或多个取代基；X为##STR2##（R.sup.1是氢原子，较低的烷基或较低的烷氧基）或##STR3##（R.sup.2是氢原子或较低的烷基）；Y为--（CH.sub.2）.sub.m --（m为0，1或2）或--CH.dbd.CH--，Z为以下式的基团：##STR4## 其中C和D的每个苯环可以有一个或多个取代基，R.sup.3和R.sup.4分别是氢或卤素原子，或较低的烷基，较低的烷氧基，较低的乙酰氧基，较低的烷氧羰基氧基，N，N-二-较低的烷基氨基羰氧基氧基，可选酯化的羧基或羟基，R.sup.5是卤素原子，或较低的烷基，较低的烷氧基，较低的乙酰氧基，较低的烷氧羰基氧基，N，N-二-较低的烷基氨基羰氧基氧基，可选酯化的羧基或羟基，R.sup.6和R.sup.7分别是氢原子或较低的烷基，n，o和p分别为1或2；l为0或1；或其盐，可用作动脉粥样硬化药物。