2-(2,6-dichlorophenyl)-1-iodoethane | 181472-07-1

• 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: 2-(2,6-dichlorophenyl)-1-iodoethane
• 英文别名: 2-(2-iodoethyl)-1,3-dichlorobenzene；1,3-Dichloro-2-(2-iodoethyl)benzene
• CAS: 181472-07-1
• 化学式: C₈H₇Cl₂I
• 分子量: 300.954
• InChiKey: PLCONOYLBSTYLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(2,6-dichlorophenyl)-1-iodoethane 在 吡啶 、 sodium hydroxide 、 硫化氢 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[2-(2,6-dichlorophenyl)ethyl]-N-[4-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists

  摘要：

  A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC50 values of the most potent antagonists were ca. 0.050 mu M in these assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.100
• 作为产物：
  描述：

  2,6-二氯苯乙酸 在 咪唑 、 硼烷 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2,6-dichlorophenyl)-1-iodoethane
  参考文献：
  名称：

  Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists

  摘要：

  A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC50 values of the most potent antagonists were ca. 0.050 mu M in these assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.100

文献信息

• Copper-catalyzed thiocarbonylation and thiolation of alkyl iodides
  作者：Qingqiang Tian、Rongjing Sun、Yahui Li

  DOI：10.1039/d2ob00008c

  日期：——

  the present study, an efficient Cu-catalyzed transthiolation of alkyl iodides is developed. Notably, in the presence of CO, thioesters could also be obtained with copper and cobalt as the co-catalyst. This transformation displayed good functional group tolerance and afforded thioesters or sulfides from the corresponding alkyl iodides.

  在本研究中，开发了一种有效的 Cu 催化烷基碘的转硫醇化。值得注意的是，在 CO 存在下，硫酯也可以用铜和钴作为助催化剂来获得。这种转化表现出良好的官能团耐受性，并从相应的烷基碘中得到硫酯或硫化物。
• Copper-Catalyzed direct thioetherification of Alkyl Halides with <i>S</i>-Alkyl Butanethioate as Thiol transfer reagent
  作者：Qingqiang Tian、Lili Wang、Yahui Li

  DOI：10.1080/17415993.2021.1967354

  日期：2022.1.2

  A new and convenient copper-catalyzed synthesis of alkyl sulfides has been accomplished using S-alkyl butanethioate as a thiol source. This catalytic protocol displayed a good functional groups tolerance and high efficiency. Both secondary and primary alkyl iodides can be used in this procedure. In addition, this method features operational simplicity and a wide substrate range, providing a complementary

  使用 S-烷基丁硫代酸酯作为硫醇源，已经完成了一种新的、方便的铜催化合成烷基硫化物。该催化方案显示出良好的官能团耐受性和高效率。二级和一级烷基碘都可用于此过程。此外，该方法操作简单，底物范围广，为烷基硫化物的合成提供了一种补充方法，不需要有毒的硫醇和贵金属。
• Organocatalytic Deoxyhalogenation of Alcohols with Inorganic Halides
  作者：Weijin Wang、Hongye Wang、Rongheng Dai、Yachong Wang、Zhaoting Li、Xiaoxue Yang、Bin Lu、Ning Jiao、Song Song

  DOI：10.1021/acscatal.3c02078

  日期：2023.7.7

  Deoxyhalogenation of alcohols represents one of the most important transformations for accessing organic halides. However, a practical catalytic protocol with readily available, inexpensive, and stable inorganic halides is still unknown. Herein, we report an organocatalytic deoxyhalogenation of alcohols with inorganic halides, which avoids the employment of stoichiometric activators and organic halogenating reagents

  醇的直接取代一直是有机化学中的热门话题。醇的脱氧卤化是获得有机卤化物的最重要的转化之一。然而，使用容易获得、廉价且稳定的无机卤化物的实用催化方案仍然未知。在此，我们报道了醇与无机卤化物的有机催化脱氧卤化，避免了化学计量活化剂和有机卤化试剂的使用。各种醇以良好的产率转化为相应的有机溴化物和碘化物。通过一锅顺序工艺，C-N、C-O、C-F、C-Cl 和 C-S 键形成也能以良好的产率实现。
• Novel heterocyclic scaffolds of GW4064 as farnesoid X receptor agonists
  作者：Terrence L. Smalley、Sharon Boggs、Justin A. Caravella、Lihong Chen、Katrina L. Creech、David N. Deaton、Istvan Kaldor、Derek J. Parks

  DOI：10.1016/j.bmcl.2014.11.050

  日期：2015.1

  The farnesoid X receptor (FXR) may play a crucial role in a number of metabolic diseases and, as such, could potentially serve as a target for the development of therapeutics as a treatment for those diseases. Previous work has described GW4064 as an FXR agonist with an interesting activity profile. This manuscript will describe the synthesis of novel analogs of GW4064 and the activity profile of those analogs. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and antifungal activity of novel aza-d--homosteroids, hydroisoquinolines, pyridines and dihydropyridines
  作者：GL Patrick、OS Kinsman

  DOI：10.1016/0223-5234(96)89557-2

  日期：1996.1

  A series of novel aza-D-homosteroids and their hydroisoquinoline precursors were synthesized and tested for antifungal activity against a variety of Candida strains and also Aspergillus species. A number of 4-substituted pyridines and tetrahydropyridines were also tested. Several compounds showed a broad spectrum of modest antifungal activity and three structures were investigated further for fungicidal and in vivo activity.