2-(m-tolyl)acrylamide | 1128278-75-0

• 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-(m-tolyl)acrylamide
• 英文别名: 2-(3-Methylphenyl)prop-2-enamide
• CAS: 1128278-75-0
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: VWGOASWFDPKZMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(m-tolyl)acryloyl chloride 在 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 2-(m-tolyl)acrylamide
  参考文献：
  名称：

  Morita, Masataka; Drouin, Ludovic; Motoki, Rie, Journal of the American Chemical Society, 2009, vol. 131, p. 3858 - 3859

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Regioselective Hydroaminocarbonylation of Alkynes to α,β-Unsaturated Primary Amides with Ammonium Chloride
  作者：Xiaolei Ji、Bao Gao、Xibing Zhou、Zongjian Liu、Hanmin Huang

  DOI：10.1021/acs.joc.8b01405

  日期：2018.9.7

  α,β-Unsaturated primary amides have found numerous applications in drug development, organic materials, and polymer sciences. However, the catalytic synthesis of α,β-unsaturated primary amides via carbonylation of alkynes has long been an elusive endeavor. Here, we report a novel palladium-catalyzed hydroaminocarbonylation of alkynes with NH4Cl as the amine source, enabling the highly chemo- and regioselective

  α，β-不饱和伯酰胺在药物开发，有机材料和聚合物科学中发现了许多应用。然而，长期以来，通过炔烃的羰基化催化合成α，β-不饱和伯酰胺一直是一项艰巨的努力。在这里，我们报告一种新型的钯催化炔烃与NH 4的加氢氨基羰基化反应Cl作为胺源，可以高度化学和区域选择性地合成α，β-不饱和伯酰胺。包括芳族炔烃，脂族炔烃，末端炔烃，内部炔烃以及具有各种官能团的二炔在内的多种炔烃反应良好。该方法将铵盐的寄生非配位能力转变为战略优势，从而使克级反应可以在0.05 mol％的催化剂存在下进行，并且具有出色的选择性。
• Hydroaminocarbonylation of Alkynes to Produce Primary <i>α</i> , <i>β</i> ‐Unsaturated Amides Using NH ₄ HCO ₃ Dually as Ammonia Surrogate and Brønsted Acid Additive
  作者：Dong‐Liang Wang、Wen‐Di Guo、Qing Zhou、Lei Liu、Yong Lu、Ye Liu

  DOI：10.1002/cctc.201800791

  日期：2018.10.9

  surrogate and Brønsted acid additive, the production of primary α,β‐unsaturated amides via hydroaminocarbonylation of alkynes was accomplished efficiently. The advantages of using the solid and inexpensive NH4HCO3 included: (1) the facile and clean manipulation without presence of stinky gaseous NH3 or liquids organic amines, (2) the inhibition of the subsequent dehydration and hydrolysis of amides due to its

  通过同时使用NH 4 HCO 3作为氨代用品和布朗斯台德酸添加剂，可以有效地完成炔烃加氢氨基羰基化生产伯α，β-不饱和酰胺。使用固体廉价的NH 4 HCO 3的优点包括：（1）容易进行清洁的操作，而没有臭味的气态NH 3或液体有机胺的存在；（2）由于其后的酰胺的脱水和水解作用受到抑制弱碱性；（3）释放的H 2 CO 3促进Pd-H催化活性物质的形成用作弱的布朗斯台德酸添加剂。此外，DPPP与天然咬入角（所述diphopshine β Ñ 91）°发现不可缺少刺激用于该反应的钯催化剂的性能。末端和内部的苯乙炔衍生物都可以用作底物，以高收率提供相应的伯α，β-不饱和酰胺，并且对支链的区域选择性极好。
• 3-SUBSTITUTED-2(ARYLALKYL)-1-AZABICYCLOALKANES AND METHODS OF USE THEREOF
  申请人：Targacept, Inc.

  公开号：EP1594869A2

  公开（公告）日：2005-11-16
• ３−置換−２（アリールアルキル）−１−アザビシクロアルカンおよびこれらの使用方法
  申请人：ターガセプト,インコーポレイテッド

  公开号：JP4828407B2

  公开（公告）日：2006-08-17
• [EN] 3-SUBSTITUTED-2(ARYLALKYL)-1-AZABICYCLOALKANES AND METHODS OF USE THEREOF<br/>[FR] 2(ARYLALKYL)-1-AZABICYCLOALCANES SUBSTITUES EN POSITION 3 ET LEURS PROCEDES D'UTILISATION
  申请人：TARGACEPT INC

  公开号：WO2004076449A2

  公开（公告）日：2004-09-10

  The present invention relates to 3-substituted-2-(arylalkyl)-1-azabicycloalkanes, methods of preparing the compounds and methods of treatment using the compounds. The azabicycloalkanes generally are azabicycloheptanes, azabicyclooctanes, or azabicyclononanes. The aryl group in the arylalkyl moiety is a 5- or 6-membered ring heteroaromatic, preferably 3-pyridinyl and 5-pyrimidinyl moieties, and the alkyl group is typically a C1-4 alkyl. The substituent at the 3-position of the 1-azabicycloalkane is a carbonyl group-containing moiety, such as an amide, carbamate, urea, thioamide, thiocarbamate, thiourea or similar functionality. The compounds exhibit activity at nicotinic acetylcholine receptors (nAChRs), particularly the a7 nAChR subtype, and are useful towards modulating neurotransmission and the release of ligands involved in neurotransmission. Methods for preventing or treating conditions and disorders, including central nervous system (CNS) disorders, which are characterized by an alteration in normal neurotransmission, are also disclosed. Also disclosed are methods for treating inflammation, autoimmune disorders, pain and excess neovascularization, such as that associated with tumor growth.