1-(2,2-dibromovinyl)-4-methoxy-1-nitrobenzene | 1312450-90-0

• 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: 1-(2,2-dibromovinyl)-4-methoxy-1-nitrobenzene
• 英文别名: 2-(2,2-Dibromoethenyl)-4-methoxy-1-nitrobenzene
• CAS: 1312450-90-0
• 化学式: C₉H₇Br₂NO₃
• 分子量: 336.967
• InChiKey: MIZVSZBHJVLWKE-UHFFFAOYSA-N

物化性质

• 沸点：
  410.5±45.0 °C(Predicted)
• 密度：
  1.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,2-dibromovinyl)-4-methoxy-1-nitrobenzene 在 potassium phosphate 、 二(三叔丁基膦)钯 、 tin(II) chloride dihdyrate 、 zinc(II) trifluoroacetate 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 18.75h， 生成 5-methoxy-1H-indole-2-carbonitrile
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of 2-Cyanoindoles from 2-gem-Dihalovinylanilines

  摘要：

  An efficient Pd(0)-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines is reported. Few methods have aimed to synthesize these scaffolds, which are found in many natural products and have high bioactivity. This protocol features a robust catalyst system utilizing Zn(TFA)(2) to prolong the catalytic activity. Additionally, the amount of cyanide in the reaction phase is minimized by taking advantage of the solubility of Zn(CN)(2) in a two-solvent mixture.

  DOI：

  10.1021/acs.orglett.7b02244
• 作为产物：
  描述：

  四溴化碳 、 5-甲氧基-2-硝基苯甲醛 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-(2,2-dibromovinyl)-4-methoxy-1-nitrobenzene
  参考文献：
  名称：

  探索N-烷基化磺胺嘧啶的反应性：酸催化的环化反应

  摘要：

  在温和的反应条件下，N-炔基化亚砜亚砜经历酸促进的环化过程。转化在较短的反应时间内进行，从而以极高的收率得到了磺酰亚胺基亚氨酰基官能化的萘并[2,1- b ]噻吩或吡咯并[1,2- a ]喹啉。

  DOI：

  10.1021/acs.orglett.6b01646

文献信息

• Palladium‐Catalyzed Domino Cyclization/Phosphorylation of <i>gem</i> ‐Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics
  作者：Chen Chen、Jie Ding、Liying Liu、Yujie Huang、Bolin Zhu

  DOI：10.1002/adsc.202100949

  日期：2022.1.4

  We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in moderate to good yields with wide functional group compatibility. This one-pot reaction enables multiple bond-forming events including C−X (X=O, N

  我们提出了钯催化环化多米诺/磷酸化宝石-dibromoolefins，其利用H-次膦酸酯和仲膦氧化物的混合物作为膦源，分别。以中等至良好的产率获得了多种磷酸化杂芳烃，并具有广泛的官能团兼容性。这种一锅法反应可以使用容易获得的起始材料实现多种键形成事件，包括 C-X (X=O, N, S) 和 C-P 键。此外，该协议可以轻松应用于大规模制备和后期功能化。
• 4-Aminophenol derivatives and colorants comprising these compounds
  申请人：Pasquier Cecile

  公开号：US20070067922A1

  公开（公告）日：2007-03-29

  4-Aminophenol derivative of the general formula (I) or physiologically compatible, water-soluble salt thereof, and agent comprising these compounds for the oxidative dyeing of keratin fibers.

  4-氨基苯酚衍生物的一般公式(I)或其生理相容的水溶性盐，以及包含这些化合物的剂，用于角蛋白纤维的氧化染色。
• Silver-Catalyzed Carbon Dioxide Fixation on Alkynylindoles
  作者：Seiya Uema、Kodai Saito、Tohru Yamada

  DOI：10.1021/acs.orglett.2c01994

  日期：2022.7.8

  A silver-catalyzed carbon dioxide fixation reaction into 2-alkynylindole derivatives was developed to afford tricyclic indoles. Carbon dioxide was selectively fixed on the N atom of the indole, and only 6-endo-dig cyclization proceeded under mild reaction conditions. Carboxylation on C3 of the indole was not observed. This method was applicable for a variety of 2-alkynylindoles, and the corresponding

  开发了一种银催化的二氧化碳固定反应到 2-炔基吲哚衍生物中，以提供三环吲哚。二氧化碳选择性地固定在吲哚的N原子上，在温和的反应条件下仅进行6-endo-dig环化。没有观察到吲哚的 C3 上的羧基化。该方法适用于多种2-炔基吲哚类化合物，并以高收率得到相应产物，且不产生副产物。
• Electrocatalytic Annulation–Iodosulfonylation of Indole‐Tethered 1,6‐Enynes to Access Pyrrolo[1,2‐<i>a</i>]indoles
  作者：Ya‐Yu Yuan、Xi Chen、Ji‐Yun Wang、Sheng‐Hu Yan、Yu‐Ting Wang、Yue Zhang、Jian‐Wu Liu、Hang‐Dong Zuo

  DOI：10.1002/ejoc.202301256

  日期：2024.3.11

  Indole tethered 1,6-enynes were designed and prepared for the first time and then used to achieve an electrochemical annulation-iodosulfonylation reaction. The reaction of indole-tethered 1,6-enynes with arylsulfonyl hydrazide and KI led to unprecedented iodosulfonated pyrrolo[1,2-a]indoles in moderate to high yields under sustainable electrochemical oxidative conditions, which may open new avenues

  首次设计和制备了吲哚束缚的1,6-烯炔，并用于实现电化学环化-碘磺酰化反应。吲哚束缚的1,6-烯炔与芳基磺酰肼和KI的反应在可持续的电化学氧化条件下以中等到高产率产生了前所未有的碘磺化吡咯并[1,2- a ]吲哚，这可能为吡咯的形成开辟新途径[1,2- a ]吲哚。
• Rapid, robust, clean, catalyst-free synthesis of 2-halo-3-carboxyindoles
  作者：Aaron R. Kunzer、Michael D. Wendt

  DOI：10.1016/j.tetlet.2011.02.037

  日期：2011.4

  A novel synthesis of 2-halo-3-carboxyindoles from 2-(2,2-dihalovinyl)anilines was discovered. Reaction conditions and substrate applicability were studied. Optimally, the reaction takes only minutes when these substrates are heated in DMSO at 120 degrees C in the presence of cesium carbonate. However, the reaction is robust and takes place at a wide range of temperatures, is tolerant of aqueous reaction conditions, and can be performed in a variety of polar solvent/carbonate base combinations where the limiting factor is base solubility. A wide range of substituents is tolerated on the 2-(2,2-dihalovinyl)anilines, and yields are generally high, requiring only acidic aqueous work-up to obtain pure products. No catalyst is required for the transformation. The mechanism is believed to involve initial formation of an alkynyl bromide intermediate followed by ring closure and carbon dioxide trapping, leading to product formation. (C) 2011 Elsevier Ltd. All rights reserved.