N-(2-丙炔基)苯胺 | 14465-74-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(2-丙炔基)苯胺
• 英文名称: N-phenyl-N-prop-2-ynylamine
• 英文别名: N-(prop-2-yn-1-yl)aniline；N-propargylaniline；N-(2-propynyl)aniline；N-(prop-2-ynyl)aniline；N-phenylpropargylamine；N‐(prop‐2‐yn‐1‐yl)aniline；N-(prop-2-ynyl)benzenamine；N-phenyl(prop-2-ynyl)amine；N-phenylprop-2-yn-1-amine；phenyl prop-2-ynylamine；N-prop-2-ynylaniline
• CAS: 14465-74-8
• 化学式: C₉H₉N
• mdl: MFCD02856314
• 分子量: 131.177
• InChiKey: IZKIWEYIOKPHLF-UHFFFAOYSA-N

物化性质

• 沸点：
  117-118.5 °C(Press: 11 Torr)
• 密度：
  1.0117 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921420090

反应信息

• 作为反应物：
  描述：

  N-(2-丙炔基)苯胺 在 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) bis(trifluoromethanesulfonyl)imide 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以20%的产率得到喹啉
  参考文献：
  名称：

  金催化邻苯二甲酰亚胺保护的炔丙基胺区域选择性水合的实验和计算证据：β-氨基酮的入门

  摘要：

  描述了我们对烷基和芳基取代的N-炔丙基邻苯二甲酰亚胺的 Au 催化区域选择性水合反应的研究结果，这些反应旨在选择性地形成相应的 β-邻苯二甲酰亚胺酮。实验数据，特别是观察到的区域选择性，已经在密度泛函理论 (DFT) 和分子中原子量子理论 (QTAIMS) 框架内对模型系统进行的量子化学计算定性支持。我们的研究结果表明，炔丙基三键和 Au( I) 催化剂，特别是金-三键相互作用的特征，对于观察到的区域选择性至关重要。其他影响，例如溶剂的存在以及水分子和邻苯二甲酰亚胺部分之间形成氢键，虽然显然与区域选择性无关，但已证明在动力学和催化上相当重要。

  DOI：

  10.1039/d0ob01598a
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-N-(prop-2-ynyl)aniline 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 N-(2-丙炔基)苯胺
  参考文献：
  名称：

  Ligand Effects in the Rhodium(II)-Catalyzed Reactions of .alpha.-Diazoamides. Oxindole Formation is Promoted by the Use of Rhodium(II) Perfluorocarboxamide Catalysts

  摘要：

  An improved procedure for the preparation of ethyl 2-diazomalonyl chloride ws developed which involves the reaction of ethyl diazoacetate with triphosgene. Using this diazo acid chloride, it was possible to prepare a variety of diazoamides from substituted amines. The rhodium(II)-catalyzed decomposition of these diazoamides was studied in order to probe the chemoselectivity of the carbenoid intermediates in intramolecular insertion reactions. Rhodium(II) acetate decomposition of N-benzyl-2-diazo-N-phenylmalonamic acid ethyl ester resulted in intramolecular C-H insertion to give ethyl 1,4-diphenyl-2-oxoazetidine-3-carboxylate. By changing the catalyst ligand to trifluoroacetamide, beta-lactam formation was completely suppressed in favor of the aromatic C-H insertion which produces an oxindole as the only detectable product. The competition between aliphatic and aromatic carbon-hydrogen insertion of 2-diazo-N-phenylmalonamic acid ethyl ester provides another example of ligand effectiveness in controlling chemoselectivity in dirhodium(II)-catalyzed metal carbene reactions. Thus, treatment of the N-isobutyldiazoanilide with rhodium(II) acetate results in exclusive aliphatic C-H insertion giving 4,4-dimethyl-2-oxo-1-phenylpyrrolidine-3-carboxylic acid ethyl ester, while the perfluorobutyramide ligand promotes oxidinole formation by aromatic C-H insertion. Several other rhodium(II)-catalyzed reactions were studied and were found to be highly catalyst dependent, rhodium(II) perfluorocarboxamides promoting aromatic C-H insertion, and hence oxindole formation, over O-H insertion, cyclization onto adjacent triple bonds, or cyclization to generate 1,3-dipolar intermediates.

  DOI：

  10.1021/jo00088a028

文献信息

• NOVEL DIHYDROPYRIMIDINOISOQUINOLINONES AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS.
  申请人：GALAPAGOS NV

  公开号：US20130165437A1

  公开（公告）日：2013-06-27

  A compound according to Formula Ia: wherein L 1 , G, and R 1 are as described herein. The present invention relates to novel compounds according to Formula I that antagonize GPR84, a G-protein-coupled receptor that is involved in inflammatory conditions, and methods for the production of these novel compounds, pharmaceutical compositions comprising these compounds, and methods for the prevention and/or treatment of inflammatory conditions (for example inflammatory bowel diseases (IBD), rheumatoid arthritis, vasculitis, lung diseases (e.g. chronic obstructive pulmonary disease (COPD) and lung interstitial diseases (e.g. idiopathic pulmonary fibrosis (IPF))), neuroinflammatory conditions, infectious diseases, autoimmune diseases, endocrine and/or metabolic diseases, and/or diseases involving impairment of immune cell functions by administering a compound of the invention.

  根据以下公式Ia的化合物： 其中L1、G和R1如本文所述。 本发明涉及根据公式I的新化合物，这些化合物对抗GPR84，G蛋白偶联受体，该受体参与炎症病症，以及这些新化合物的生产方法，包含这些化合物的药物组合物，以及通过给予本发明的化合物来预防和/或治疗炎症病症（例如炎症性肠病（IBD）、类风湿关节炎、血管炎、肺部疾病（例如慢性阻塞性肺病（COPD）和肺间质疾病（例如特发性肺纤维化（IPF）））、神经炎症病症、传染病、自身免疫疾病、内分泌和/或代谢疾病，以及/或通过给予本发明的化合物导致免疫细胞功能受损的疾病。
• Deoxygenative C2-heteroarylation of quinoline <i>N</i>-oxides: facile access to α-triazolylquinolines
  作者：Geetanjali S Sontakke、Rahul K Shukla、Chandra M R Volla

  DOI：10.3762/bjoc.17.42

  日期：——

  A metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated

  通过容易获得的N-氧化物和N-磺酰基-1,2,3-三唑可实现喹啉和异喹啉的无金属和无添加剂，高效，经济的步骤脱氧C2-杂芳基化。在温和的反应条件下，以良好的区域选择性和优异的产率合成了多种α-三唑基喹啉衍生物。进一步，克级和一锅法合成说明了所开发协议的有效性和简单性。还发现当前的转化与天然产物的后期改性相容。
• Facile <i>N</i>-Arylation of Amines and Sulfonamides and <i>O</i>-Arylation of Phenols and Arenecarboxylic Acids
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1021/jo0602221

  日期：2006.4.1

  An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates

  通过使这些底物在存在下与多种邻甲硅烷基芳基三氟甲磺酸酯反应，已实现了一种有效的，无过渡金属的胺，磺酰胺和氨基甲酸酯的N-芳基化以及酚和羧酸的O-芳基化方法。的CsF。在非常温和的反应条件下，芳基化产物的收率好至极好。这种化学反应易于耐受各种官能团。
• Synthesis of Substituted Quinolines by Electrophilic Cyclization of <i>N</i>-(2-Alkynyl)anilines
  作者：Xiaoxia Zhang、Marino A. Campo、Tuanli Yao、Richard C. Larock

  DOI：10.1021/ol0476218

  日期：2005.3.1

  Quinolines substituted in the 3-position by an iodo or phenylseleno group are readily prepared in good to excellent yields by the reaction of propargylic anilines with appropriate electrophiles under mild reaction conditions. [reaction: see text]

  在温和的反应条件下，通过炔丙基苯胺与合适的亲电试剂的反应，可以很容易地制备在3位被碘或苯基硒烯基取代的喹啉。[反应：看文字]
• [EN] TRICYCLIC PYRAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES A BASE DE TYRAZOLES TRICYCLIQUES
  申请人：ABBOTT LAB

  公开号：WO2005095387A1

  公开（公告）日：2005-10-13

  Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  本发明的化合物对抑制蛋白酪氨酸激酶具有用处。还公开了制备这些化合物的方法、含有这些化合物的组合物以及使用这些化合物进行治疗的方法。