N-hydroxy-4-iodobenzenecarboxyimidoyl chloride | 29305-61-1

• 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: N-hydroxy-4-iodobenzenecarboxyimidoyl chloride
• 英文别名: N-hydroxy-4-iodobenzimidoyl chloride；4-iodo-N-hydroxybenzimidoyl chloride；N-hydroxy-4-iodobenzenecarboximidoyl chloride
• CAS: 29305-61-1
• 化学式: C₇H₅ClINO
• 分子量: 281.48
• InChiKey: FELCGMDWRKKFFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hydroxy-4-iodobenzenecarboxyimidoyl chloride 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 、 sodium azide 、 水 、 二甲羟胺盐酸盐 、 二甲基亚砜 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.83h， 生成 N-(4-(3-(4-(3-(cyclopropylmethoxy)phenoxy)phenyl)-1,2-oxazol-5-yl)butan-2-yl)acetamide
  参考文献：
  名称：

  MONOCYCLIC COMPOUND

  摘要：

  公开号：

  EP3279183B1
• 作为产物：
  描述：

  4-碘苯甲醛 在 N-氯代丁二酰亚胺 、 盐酸羟胺 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-hydroxy-4-iodobenzenecarboxyimidoyl chloride
  参考文献：
  名称：

  膦催化的 4-硝基异恶唑与联烯酸酯或 Morita-Baylis-Hillman 碳酸盐的脱芳香 [3+2] 环加成反应

  摘要：

  已经建立了一种高效的膦催化的 4-硝基异恶唑与联烯酸酯或 Morita-Baylis-Hillman 碳酸酯的脱芳香 [3+2] 成环反应，可方便地合成双环异恶唑啉衍生物。该反应方法显示出广泛的底物范围、高官能团兼容性以及优异的区域选择性和非对映选择性。此外，所获得的化合物3a在克级和合成应用上的成功证明了该方法在有机合成实际应用中的巨大潜力。

  DOI：

  10.1039/d4cc02231a

文献信息

• Synthesis of 1,2,4-Oxadiazolines through Deoxygenative Cyclization of <i>N</i>-Vinyl-α,β-Unsaturated Nitrones with <i>in Situ</i> Generated Nitrile Oxides from Hydroxamoyl Chlorides
  作者：Cai-Mei Nong、Si-Ning Lv、Wei-Min Shi、Cui Liang、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1021/acs.orglett.2c04121

  日期：2023.1.13

  derivatives were synthesized in moderate to good yields through a deoxygenative cyclization cascade reaction of N-vinyl-α,β-unsaturated nitrones and hydroxamoyl chlorides. Mechanistic studies revealed that the reaction underwent double additions of nitrile oxides to N-vinyl-α,β-unsaturated nitrones, sequential elimination, and intramolecular cyclization to afford 1,2,4-oxadiazolines. Alternatively, 1,2,5-oxadiazolines

  通过N-乙烯基-α,β-不饱和硝酮和异羟氨酰氯的脱氧环化级联反应，合成了多种 1,2,4-恶二唑啉衍生物，收率适中。机理研究表明，该反应经历了氧化腈与N-乙烯基-α,β-不饱和硝酮的双重加成、顺序消除和分子内环化，得到 1,2,4-恶二唑啉。或者，通过 [3 + 3] 环加成和选择性 [3,3]-重排，1,2,5-恶二唑啉也作为主要产物在i - PrOH 溶剂中获得。此外，所制备的 1,2,4-恶二唑啉在热条件下很容易转化为多取代吡咯。
• Asymmetric Synthesis of Bicyclic Isoxazolines via Dearomative Cycloaddition of 4-Nitroisoxazoles with Zwitterionic π-Allyl Palladium Species
  作者：Taiki Morita、Non Ito、Hiroyuki Nakamura

  DOI：10.1021/acs.orglett.3c01324

  日期：2023.7.7

  (S)-DTBM-SEGPHOS to give the corresponding bicyclic isoxazolines 3 and 4 in good to high yields with excellent enantioselectivities (≤99% ee). This synthetic approach could be applied to N-tosyl vinyl aziridine and 2-methylidenetrimethylene carbonate. Further transformations of the resulting cycloadducts 4a and 4i yielded not only its derivatives 10 and 11 but also the novel tetracyclic skeleton 12.

  在 Pd 2 (dba) 3和 ( S )-DTBM-SEGPHOS存在下，4-硝基异恶唑与乙烯基碳酸亚乙酯 ( 2 ) 发生对映选择性脱芳环加成反应，以良好到高产率和优异的对映选择性生成相应的双环异恶唑啉3和4 ( ≤99% ee）。该合成方法可应用于N-甲苯磺酰基乙烯基氮丙啶和2-亚甲基三亚甲基碳酸酯。所得环加合物4a和4i的进一步转化不仅产生了其衍生物10和11，还产生了新型四环骨架12。
• Discovery of 3-Amino-4-Chlorophenyl P1 as a novel and potent benzamidine mimic via solid-phase synthesis of an isoxazoline library
  作者：Patrick Y.S. Lam、Jessica J. Adams、Charles G. Clark、W.Jason Calhoun、Joseph M. Luettgen、Robert M. Knabb、Ruth R. Wexler

  DOI：10.1016/s0960-894x(03)00130-6

  日期：2003.5

  In an effort to identify orally bioavailable factor Xa inhibitors, two isoxazolines libraries were prepared to scan for novel P1 ligands. From this work, 4-chloro-3-aniline was identified as a novel and potent benzamidine mimic. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and evaluation of isoxazole derivatives as lysophosphatidic acid (LPA) antagonists
  作者：Takashi Yamamoto、Koichi Fujita、Sayaka Asari、Akira Chiba、Yuka Kataba、Koji Ohsumi、Naoko Ohmuta、Yuko Iida、Chiori Ijichi、Satoshi Iwayama、Naoyuki Fukuchi、Masataka Shoji

  DOI：10.1016/j.bmcl.2007.04.024

  日期：2007.7

  A series of isoxazole derivatives were synthesized and their antagonistic activities against LPA stimulation on both LPA(1)/ CHO cells and rHSC cells were evaluated. Among them, 3 -(4-4- [1 -(2-chloro-cyclopent-1-enyl) -ethoxycarbonylamino] -isoxazol - 3- yl}-benzylsulfanyl)-propionic acid (34) showed the most potent activities. (c) 2007 Elsevier Ltd. All rights reserved.
• N-Hydroxy-(4-oxime)-cinnamide: A versatile scaffold for the synthesis of novel histone deacetilase (HDAC) inhibitors
  作者：Giuseppe Giannini、Mauro Marzi、Riccardo Pezzi、Tiziana Brunetti、Gianfranco Battistuzzi、Maria Di Marzo、Walter Cabri、Loredana Vesci、Claudio Pisano

  DOI：10.1016/j.bmcl.2009.02.029

  日期：2009.4

  With the aim to discover novel HDAC inhibitors with high potency and good safety profiles, we have designed a small library based on a N-hydroxy-(4-oxime)-cinnamide scaffold. We describe the synthesis of these novel compounds and some preliminary in vitro cytotoxic activity on three tumor cell lines, NB4, H460 and HCT116, as well as their inhibitory activity against class I, II and IV HDAC. Several 4-oxime derivatives demonstrated a promising inhibitory activity on HDAC6 and HDAC8 coupled to a good selectivity profile. (C) 2009 Elsevier Ltd. All rights reserved.