1-Chlor-3-iod-6-nitro-benzol | 89284-60-6

• 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-Chlor-3-iod-6-nitro-benzol
• 英文别名: 2-Chlor-4-iod-1-nitro-benzol；2-Chlor-4-iod-nitrobenzol；2-chloro-4-iodo-1-nitro-benzene；2-Chlor-4-jod-1-nitro-benzol；2-Chloro-4-iodo-1-nitrobenzene
• CAS: 89284-60-6
• 化学式: C₆H₃ClINO₂
• 分子量: 283.453
• InChiKey: XFZDMPIWHWAUGI-UHFFFAOYSA-N

物化性质

• 熔点：
  63 °C
• 沸点：
  320.3±27.0 °C(Predicted)
• 密度：
  2.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Chlor-3-iod-6-nitro-benzol 在 乙醇 、 铁粉 、 溶剂黄146 作用下， 生成 4-iodo-N²,N²-dimethyl-o-phenylenediamine
  参考文献：
  名称：

  LXIX.—3-卤代-6-硝基和-6-氨基-二甲基苯胺

  摘要：

  DOI：

  10.1039/jr9300000497
• 作为产物：
  描述：

  3-氯-4-硝基苯胺 生成 1-Chlor-3-iod-6-nitro-benzol
  参考文献：
  名称：

  Mayes; Turner, Journal of the Chemical Society, 1928, p. 693

  摘要：

  DOI：

文献信息

• One-Pot Regioselective Synthesis of 5-Amino-3-Benzyl-7<i>H</i>-[1,3]Thiazolo[3,2-<i>A</i>]Pyrimidin-7-Ones via Sonogashira Coupling Reaction
  作者：Ali Keivanloo、Mohammad Bakherad、Mahboobe Rajaei

  DOI：10.1080/10426507.2014.885972

  日期：2014.11.2

  6-amino-2-(prop-2-yn-1-ylsulfanyl)pyrimidin-4(1H)-one with various iodobenzenes in the presence of a Pd-Cu catalyst leads to the regioselective cyclization to 5-amino-3-benzyl-7H-[1,3]thiazolo[3,2-a]pyrimidin-7-ones. This one-pot procedure is very simple, and affords good-to-high yields.

  图形摘要 摘要 6-amino-2-(prop-2-yn-1-ylsulfanyl)pyrimidin-4(1H)-one 与各种碘苯在 Pd-Cu 催化剂存在下的反应导致区域选择性环化为 5 -amino-3-benzyl-7H-[1,3]thiazolo[3,2-a]pyrimidin-7-ones。这种一锅法非常简单，产量从好到高。
• Pd-catalyzed coupling reaction of 6-hydroxy-2-(prop-2-yn-1-ylsulfanyl)pyrimidin-4(1H)-one with aryl iodides: efficient syntheses of new 3-benzylthiazolo[3,2-a]pyrimidinones
  作者：Ali Keivanloo、Mohammad Bakherad、Taraneh Shahani、Amir Hossein Amin

  DOI：10.1007/s10593-016-1974-8

  日期：2016.10

  protocol was developed for the preparation of 3-benzyl-7(5)-hydroxy-5(7)H-[1,3]thiazolo[3,2-a]pyrimidin-5(7)-ones from 6-hydroxy-2-(prop-2-yn-1-ylsulfanyl)pyrimidin-4(1H)-one and aryl iodides in the presence of Pd–Cu complex catalyst. This one-pot process provides a simple and direct method for the synthesis of new thiazolo[3,2-a]pyrimidinones in good to high yields.

  开发了一种有效的合成方案，用于从6中制备3-苄基-7（5）-羟基-5（7）H- [1,3]噻唑洛[3,2- a ]嘧啶-5（7）- Pd-Cu络合物催化剂存在下的-羟基-2-（prop-2-yn-1-ylsulfanyl）pyrimidin-4（1 H）-one和芳基碘化物。这一一锅法为高产率到高产率的新型噻唑并[3，2- a ]嘧啶酮的合成提供了一种简单直接的方法。
• Aryl alkynylation versus alkyne homocoupling: unprecedented selectivity switch in Cu, phosphine and solvent-free heterogeneous Pd-catalysed couplings
  作者：Marco Bandini、Rafael Luque、Vitaly Budarin、Duncan J. Macquarrie

  DOI：10.1016/j.tet.2005.06.082

  日期：2005.10

  Sonogashira reaction and oxidative dimerisation of terminal alkynes are among the most relevant and attractive C-C bond forming transformations in the metallo-catalysed cross-coupling scenario. Often, the homocoupling reactions of substituted acetylenic derivatives are concomitant to the Sonogashira pathway and time-consuming optimization procedures are required in order to reach satisfactory levels of selectivity. In this paper, the potential of a class of Pd-complexes loaded to mesoporous silica gel in promoting the Sonogashira reaction between aryl acetylenes and iodoarenes is underlined. This family of heterogeneous organo-palladium systems allows the desired cross-coupled compounds to be isolated in excellent yield under very mild conditions. In fact, the absence of organic solvents, copper(I) co-catalyst and phosphane ligands, (which are easily oxidisable and whose preparation has a heavy environmental impact), in conjunction with the low catalyst loading ([Pd] 0.1-1 mol%) and its recoverability, stresses the environmental benefits of the protocol. The Sonogashira/homocoupling selectivity proved to be function of the haloarene employed. As a matter of fact, while iodoarenes bearing EWG (electron withdrawing groups) on the phenyl ring underwent smoothly the Sonogashira pathway, electron-rich iodobenzenes showed opposite behaviour by mainly furnishing the homocoupling product. The use of bromoarenes provided solely the homocoupling product in excellent yield without themselves being consumed. This is despite that fact that the catalysts used activate bromoarenes equally as well as iodoarenes in both Heck and Suzuki systems. Kinetic investigations revealed a highly temperature-dependent profile, which indicates strongly that the reaction takes place at the surface. Finally, the full heterogeneous character of the catalytically active species as well as the reusability of the immobilised Pd-complex were confirmed by hot-filtration test and by multiple reuses of the supported catalyst in subsequent Sonogashira cross-couplings. (c) 2005 Elsevier Ltd. All rights reserved.
• <b>Polar Effects of Substitutents on the Reaction Rates of 4-R- and 5-R-2-Nitrochlorobenzenes with Piperidine in Benzene</b>
  作者：W. Greizerstein、R. A. Bonelli、J. A. Brieux

  DOI：10.1021/ja00865a031

  日期：1962.3
• Regioselective Syntheses of 1-Aryl-substituted-5<i>H</i>-[1,3]thiazolo[3,2-<i>a</i>]quinazoline-5-ones During Sonogashira Coupling
  作者：Mohammad Bakherad、Ali Keivanloo、Zahra Kalantar、Vahid Keley

  DOI：10.1080/10426507.2010.503211

  日期：2011.2.28

  Reaction of 2-mercaptopropargylquinazoline-4-one with various aryliodides catalyzed by Pd-Cu leads to the regioselective formation of 1-arylsubstituted-5H-[1,3] thiazolo[ 3,2-a] quinazoline-5-ones.