2-Chlor-phenylessigsaeure-methylamid | 99846-64-7

• 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: 2-Chlor-phenylessigsaeure-methylamid
• 英文别名: 2-(2-Chlorophenyl)-N-methylacetamide
• CAS: 99846-64-7
• 化学式: C₉H₁₀ClNO
• mdl: MFCD18827577
• 分子量: 183.637
• InChiKey: FJVUQHBJXQNKHS-UHFFFAOYSA-N

物化性质

• 熔点：
  108.5-110 °C
• 沸点：
  361.8±25.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Chlor-phenylessigsaeure-methylamid 在 lithium aluminium tetrahydride 作用下， 反应 24.0h， 生成 2-(2-氯氯苯基)-n-甲基乙胺
  参考文献：
  名称：

  Formamidines in synthesis. An efficient one-pot synthesis of 7-substituted indolines via intramolecular cyclization of (2-phenethyl)formamidines. An asymmetric route to benzopyrrocoline alkaloids

  摘要：

  o-Chloro-beta-phenethylamines, transformed into the N-tert-butylformamidines, were found to be excellent precursors to indolines following benzyne formation. A series of methoxy-substituted o-chlorophenethylamines containing an N-alkyl or aryl substitutent were subjected to sec-butyllithium producing the ortho-lithiated aromatic which subsequently lost lithium chloride at temperatures ranging from -78 to -50-degrees-C. The resulting benzyne was intramolecularly trapped providing the titled heterocycles. Quenching the reaction resulted in elimination of the tert-butyl isocyanide (isolated after aqueous workup as tert-butylformamide) and protonation (or alkylation) of the 7-lithio position. Overall the yields for this process were 60-95% for a variety of N-substituted phenethylamines. In addition, a one-pot total asymmetric route to benzopyrrocoline alkaloids was featured using this benzyne trapping of chiral formamidines.

  DOI：

  10.1021/jo00039a029
• 作为产物：
  描述：

  2-氯苯乙醛 、 甲胺 生成 2-Chlor-phenylessigsaeure-methylamid
  参考文献：
  名称：

  Formamidines in synthesis. An efficient one-pot synthesis of 7-substituted indolines via intramolecular cyclization of (2-phenethyl)formamidines. An asymmetric route to benzopyrrocoline alkaloids

  摘要：

  o-Chloro-beta-phenethylamines, transformed into the N-tert-butylformamidines, were found to be excellent precursors to indolines following benzyne formation. A series of methoxy-substituted o-chlorophenethylamines containing an N-alkyl or aryl substitutent were subjected to sec-butyllithium producing the ortho-lithiated aromatic which subsequently lost lithium chloride at temperatures ranging from -78 to -50-degrees-C. The resulting benzyne was intramolecularly trapped providing the titled heterocycles. Quenching the reaction resulted in elimination of the tert-butyl isocyanide (isolated after aqueous workup as tert-butylformamide) and protonation (or alkylation) of the 7-lithio position. Overall the yields for this process were 60-95% for a variety of N-substituted phenethylamines. In addition, a one-pot total asymmetric route to benzopyrrocoline alkaloids was featured using this benzyne trapping of chiral formamidines.

  DOI：

  10.1021/jo00039a029

文献信息

• Derivatives Of Pentose Monosaccharides As Anti-Inflammatory Compounds
  申请人：Sattigeri Viswajanani Jitendra

  公开号：US20090075909A1

  公开（公告）日：2009-03-19

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds of this invention can be useful for inhibition and prevention of inflammation and associated pathologies, including inflammatory and autoimmune diseases, for example, bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection or psoriasis. The present invention also relates to pharmacological compositions containing these monosaccharide derivatives, as well as methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, type I diabetes, psoriasis, allograft rejection, and other inflammatory and/or auto immune disorders.

  本发明涉及单糖衍生物作为抗炎药剂。本发明的化合物可用于抑制和预防炎症及相关病理，包括炎症性和自身免疫性疾病，例如支气管哮喘、类风湿关节炎、I 型糖尿病、多发性硬化症、移植排斥或牛皮癣。本发明还涉及含有这些单糖衍生物的药物组合物，以及治疗支气管哮喘、慢性阻塞性肺病、类风湿关节炎、多发性硬化症、I 型糖尿病、牛皮癣、移植排斥和其他炎症和/或自身免疫性疾病的方法。
• Imidazole compounds
  申请人：——

  公开号：US20020058659A1

  公开（公告）日：2002-05-16

  A novel class of imidazo heterocyclic compounds, pharmaceutical compositions comprising them and use thereof in the treatment and/or prevention of diseases and disorders related to the histamine H3 receptor. More particularly, the compounds are useful for the treatment and/or prevention of diseases and disorders in which an interaction with the histamine H3 receptor is beneficial.

  一种新型的咪唑杂环化合物类，包括它们的药物组合物以及在治疗和/或预防与组织胺H3受体相关的疾病和疾病的用途。更具体地说，这些化合物对于治疗和/或预防与组织胺H3受体相互作用有益的疾病和疾病是有用的。
• FUSED RING COMPOUND AND APPLICATION THEREOF
  申请人：Wuhan LL Science and Technology Development Co., Ltd.

  公开号：EP4079724A1

  公开（公告）日：2022-10-26

  Disclosed is a fused ring compound and an application thereof. Disclosed is a fused ring compound represented by formula I, a pharmaceutically acceptable salt, a stereoisomer, a tautomer, an isotope compound, a crystal form, a nitrogen oxide, a solvate, or a solvate of the pharmaceutically acceptable salt thereof. The fused ring compound of the present invention has high P2X4 antagonistic activity, excellent selectivity, low toxicity and excellent metabolic stability.

  本发明公开了一种融合环化合物及其应用。公开了一种由公式I表示的融合环化合物，其药学上可接受的盐、立体异构体、互变异构体、同位素化合物、晶体形态、氮氧化物、溶剂合物或其药学上可接受的盐的溶剂合物。本发明的融合环化合物具有高P2X4拮抗活性、优异的选择性、低毒性和优异的代谢稳定性。
• [EN] AROMATIC COMPOUND, AND PREPARATION METHOD THEREFOR AND APPLICATION THEREOF<br/>[FR] COMPOSÉ AROMATIQUE, SON PROCÉDÉ DE PRÉPARATION ET SON APPLICATION<br/>[ZH] 一种芳香化合物、其制备方法及应用
  申请人：WUHAN LL SCIENCE AND TECH DEVELOPMENT CO LTD

  公开号：WO2022161416A1

  公开（公告）日：2022-08-04

  公开了式I所示的化合物、其药学上可接受的盐、其立体异构体、其互变异构体或其同位素化合物。该化合物具有较高的P2X4拮抗活性、较好的安全性以及药代动力学性质。
• Copper‐Catalyzed C−H (Phenylsulfonyl)difluoromethylation of Acrylamides: Scope, Mechanism, and Critical Role of Additives
  作者：Enzo Nobile、Floriane Doche、Thomas Castanheiro、Djamaladdin G. Musaev、Tatiana Besset

  DOI：10.1002/chem.202303362

  日期：2024.2.7

  Herein, we report the Cu‐complex catalyzed, native functional group‐assisted, and TFA/NMF additives promoted (phenylsulfonyl)difluoromethylation of vinylic C(sp²)−H bond of acrylamides. Using our in‐home designed reagent, this reaction enables the construction of the C(sp²)−CF₂SO₂Ph bond from simple C−H bond activation by copper catalysis under mild reaction conditions with total Z‐selectivity. The versatility of utilized fluorinated group was illustrated by its conversion into value‐added CF₂ moieties as well as the remarkable =CHF residue. The performed experimental and computational mechanistic studies enabled to identify the true nature of active catalyst and substrate, as well as establish critical roles of TFA and NMF additives. In this reaction, the TFA acts as a promoter of the much‐needed Cu^II/Cu^II→Cu^III/Cu^I disproportionation, while the NMF facilitates the following ligand exchange and C−C coupling processes. We ruled out the generation of radical intermediates and established the C−H activation to be irreversible and the rate‐determining step of the entire process.

  摘要我们在此报告了铜络合物催化、原生官能团辅助和 TFA/NMF 添加剂促进的丙烯酰胺乙烯基 C(sp2)-H键（苯磺酰基）二氟甲基化反应。利用我们自行设计的试剂，该反应可在温和的反应条件下，通过铜催化从简单的 C-H 键活化生成 C(sp2)-CF2SO2Ph 键，并具有完全的 Z 选择性。利用氟化基团将其转化为高附加值的 CF2 分子以及显著的 =CHF 残基，说明了氟化基团的多功能性。通过实验和计算机理研究，确定了活性催化剂和底物的真正性质，并确定了反式脂肪酸和 NMF 添加剂的关键作用。在这一反应中，反式脂肪酸对急需的 CuII/CuII→CuIII/CuI 歧化起到了促进作用，而 NMF 则促进了接下来的配体交换和 C-C 偶联过程。我们排除了自由基中间产物的产生，并确定 C-H 活化是不可逆的，而且是整个过程的速率决定步骤。