3-(2-iodophenyl)acrylonitrile

• 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-(2-iodophenyl)acrylonitrile
• 英文别名: 2-iodocinnamonitrile；3-(2-iodophenyl)prop-2-enenitrile
• 化学式: C₉H₆IN
• 分子量: 255.058
• InChiKey: GKYCNCYYESLGTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-iodophenyl)acrylonitrile 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2-呋喃基)膦 、 potassium carbonate 、 三氟乙酸 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、50.0 kPa 条件下， 反应 44.0h， 生成 N-(2-aminophenyl)-4-{[1-(cyanomethyl)-4-methylene-3,4-dihydroisoquinolin-2(1H)-yl]sulfonyl}benzamide
  参考文献：
  名称：

  [EN] N- (2 -AMINOPHENYL) BENZAMIDE DERIVATIVES AS HISTONE DEACETYLASE INHIBITORS
  [FR] DÉRIVÉS DE N-(2-AMINOPHÉNYL)BENZAMIDE EN TANT QU'INHIBITEURS D'HISTONE DÉSACÉTYLASE

  摘要：

  这项发明涉及发现具有HDAC抑制活性的新化合物或其药用可接受的盐，特别是该发明的化合物表现出对I类HDAC酶的选择性，并因此预计对其抗增殖活性和在人体或动物体内治疗方法中具有用处，例如在预防或抑制癌症中的肿瘤生长和转移方面。该发明还涉及用于制造此处定义的化合物或其药用可接受的盐的方法，包含它们的药物组合物以及它们在制造用于在温血动物（如人类）中产生抗增殖效果的药物中的用途。

  公开号：

  WO2013005049A1

文献信息

• Synthesis of carbo- and heterocycles via palladium catalysed cascade allene insertion–nucleophile incorporation–Michael addition processes
  作者：Ronald Grigg、Martyn Inman、Colin Kilner、Ines Köppen、John Marchbank、Peter Selby、Visuvanathar Sridharan

  DOI：10.1016/j.tet.2007.03.044

  日期：2007.7

  Novel palladium catalysed two- and three-component thermal (conventional heating and microwave) cascade processes are described involving allenylation of an aryl iodide to generate a (π-allyl)palladium species, which are intercepted (inter- or intramolecularly) by a carbon or nitrogen nucleophile followed by intramolecular Michael addition to afford carbo- and heterocycles in good yields.

  描述了新颖的钯催化的二元和三元热（常规加热和微波）级联过程，涉及芳基碘化物的烯丙基化以生成（π-烯丙基）钯物质，其被碳或碳原子截获（分子间或分子内）。氮亲核试剂，然后分子内迈克尔加成，以高收率提供碳环和杂环。
• Regioselective Synthesis of <i>N</i>-Aminoisoindolones and Mono-<i>N</i>- and Di-<i>N,N</i>′-substituted Phthalazones Utilizing Hydrazine Nucleophiles in a Palladium-Catalyzed Three-Component Cascade Process
  作者：Ronald Grigg、Visuvanathar Sridharan、Mufakhrul Shah、Simon Mutton、Colin Kilner、David MacPherson、Peter Milner

  DOI：10.1021/jo800822p

  日期：2008.11.7

  A palladium-catalyzed three-component cascade process for the synthesis of isoindolone and phthalazone derivatives is reported. The cascade process involves carbonylation of an aryl iodide/Michael acceptor to give an acylpalladium species which is intercepted by a hydrazine nucleophile. Intramolecular Michael addition follows to give either N-aminoisoindolones or mono- N- and di-N,N'-phthalazones depending

  报道了钯催化的三组分级联方法，用于合成异吲哚酮和酞菁衍生物。级联过程涉及芳基碘/迈克尔受体的羰基化，以得到酰基肼类物质，其被肼亲核试剂拦截。取决于是否使用单取代或1，2-二取代的肼亲核试剂，分子内迈克尔加成随后给出N-氨基异吲哚酮或单-N-和二-N，N'-邻苯二氮酮。
• N- (2 -AMINOPHENYL) BENZAMIDE DERIVATIVES AS HISTONE DEACETYLASE INHIBITORS
  申请人：Grigg Ronald Ernest

  公开号：US20140135327A1

  公开（公告）日：2014-05-15

  This invention relates to the discovery of novel compounds, or pharmaceutically acceptable salts thereof, which possess HDAC inhibitory activity. In particular, the compounds of the invention demonstrate selectivity towards Class I HDAC enzymes, and are accordingly expected to be useful for their anti-proliferative activity and in methods of treatment of the human or animal body, for example in preventing or inhibiting tumour growth and metastasis in cancers. The invention also relates to processes for the manufacture of the compounds defined herein, or pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments for use in the production of an anti-proliferative effect in a warm-blooded animal such as man.

  本发明涉及发现具有HDAC抑制活性的新化合物或其药学上可接受的盐。特别是，本发明的化合物表现出对I类HDAC酶的选择性，并因此预计在抗增殖活性和治疗人类或动物身体的方法中有用，例如在预防或抑制癌症中的肿瘤生长和转移。本发明还涉及制造上述化合物或其药学上可接受的盐的过程，含有它们的药物组合物以及它们在制造用于在温血动物（例如人）中产生抗增殖效应的药物中的使用。
• Synthesis of carbo- and heterocycles via a palladium-catalysed allene insertion–nucleophile incorporation–Michael addition cascade
  作者：Xinjie Gai、Ronald Grigg、Ines Köppen、John Marchbank、Visuvanathar Sridharan

  DOI：10.1016/j.tetlet.2003.08.034

  日期：2003.9

  A novel palladium catalysed three-component cascade process is described involving allenylation of an aryl iodide to generate a (pi-allyl)palladium species which is intercepted by a carbon or nitrogen nucleophile followed by intramolecular Michael addition to afford carbo- and heterocycles in good yield. (C) 2003 Elsevier Ltd. All rights reserved.