4,4-(2-chloroethane-1,1-diyl)bis(methoxybenzene) | 4957-05-5

• 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: 4,4-(2-chloroethane-1,1-diyl)bis(methoxybenzene)
• 英文别名: 1,1'-(2-chloroethane-1,1-diyl)bis(4-methoxybenzene)；1-Chlor-2,2-bis-(4-methoxy-phenyl)-ethan；2-Chlor-1,1-bis-(4-methoxy-phenyl)-ethan；1,1-bis(4-methoxyphenyl)-2-chloroethane；Ethane, 2-chloro-1,1-bis(p-methoxyphenyl)-；1-[2-chloro-1-(4-methoxyphenyl)ethyl]-4-methoxybenzene
• CAS: 4957-05-5
• 化学式: C₁₆H₁₇ClO₂
• 分子量: 276.763
• InChiKey: LEUKKGBHLCIKOA-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  401.4±45.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲氧滴滴涕 在 三乙基硅烷 、 {Rh(H)[SiMe₂(o-C₆H₄SMe)](PPh₃)₂}[BAr^F₄] 作用下， 以 neat (no solvent) 为溶剂， 反应 72.0h， 生成 4,4-(2-chloroethane-1,1-diyl)bis(methoxybenzene)
  参考文献：
  名称：

  叔硅烷对 Rh（iii）催化的烷基卤化物的无溶剂加氢脱卤†

  摘要：

  使用不饱和甲硅烷基-氢化物-Rh（III）配合物{Rh（H）[SiMe 2（o -C 6 H 4 SMe）] ，通过不同的叔硅烷有效催化还原CDCl 3和其他烷基卤，包括持久性有机污染物。完成了作为预催化剂的（PPh 3）2 } [BAr F 4 ]。反应以无溶剂的方式进行。由于实验证据，建议简化的催化循环用于CDCl 3的加氢脱卤。

  DOI：

  10.1039/c8dt03703e

文献信息

• Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (<i>n+1</i>)-Halomethyl-Alkanes
  作者：Margherita Miele、Andrea Citarella、Thierry Langer、Ernst Urban、Martin Zehl、Wolfgang Holzer、Laura Ielo、Vittorio Pace

  DOI：10.1021/acs.orglett.0c02831

  日期：2020.10.2

  The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high

  据报道，将类胡萝卜素和氢化物顺序安装在羰基上，提供了卤代甲基烷基衍生物。尽管在与以碳为中心的亲电子试剂的反应中使用类胡萝卜素作为亲核试剂，sp 3型烷基卤化物仍然是用于选择性一碳同系物的难以捉摸的材料。我们的策略是利用羰基化合物作为起始原料，从而能够均匀地实现高收率和化学控制。该策略是灵活的，不仅限于类胡萝卜素。而且，各种类似碳负离子的物种可以充当亲核试剂，因此使其具有普遍的适用性。
• Synthese einiger auxochromhaltiger ?,?-Diaryl�thylene und Stilbene
  作者：Yousef Al-Attar、Robert Wizinger

  DOI：10.1002/hlca.19630460423

  日期：——

  guter Ausbeute erhalten werden. Die auxochromhaltigen α, α-Diaryl-β-halogenäthane, in höher siedenden Lösungsmitteln bei Abwesenheit von Alkali erhitzt, spalten Halogenwasserstoff unter Umlagerung in Stilbene ab; die Ausbeuten sind vielfach praktisch quantitativ.

  茴香醇，对苯二酚，硫代苯甲醚，对-Kresolmethylather，Veratrol，2,5-二甲氧基甲苯，邻苯三酚三甲基醚，α-萘甲酰三甲基醚氯化物。溴乙醛zu，β-二芳基-β-卤代酮kondensiert，aus denen durch Abspal-tung von Halogenwasserstoff类似醇α，α-二芳基-ä在湿润的Ausbeute erhalten werden中。Dieauxochromhaltigenα，α-二芳基-β-卤代ä烷，位于Stilbene ab的Uhlagerung的HöhersiedendenLösungsmitteln中，位于alumerung的Salten Halogenwasserstoff。死于奥斯丁·辛德·维弗拉赫·定量论。
• Preparation of 4,4-dioxy-substituted stilbenes
  申请人：Monsanto Company

  公开号：US04189610A1

  公开（公告）日：1980-02-19

  Dehydrohalogenation-rearrangement of 1,1-bis(4-oxy-substituted aryl)-2-haloethanes to yield 4,4'-dioxysubstituted stilbenes is effected by heating an acidic reaction medium comprising the 1,1-bis(4-oxy-substituted aryl)-2-haloethane dissolved in a solution of an aliphatic carboxylic acid and a carboxylic acid salt. The process is particularly directed to the preparation of 4,4'-dihydroxystilbene from 1,1-bis(4-hydroxyphenyl)-2-chloroethane.

  将1,1-双(4-氧基取代芳基)-2-卤代乙烷进行脱卤-重排反应，得到4,4'-二氧基取代的苯乙烯，方法是在酸性反应介质中加热，该介质含有1,1-双(4-氧基取代芳基)-2-卤代乙烷、脂肪族羧酸和羧酸盐的溶液。该方法特别适用于从1,1-双(4-羟基苯基)-2-氯乙烷制备4,4'-二羟基苯乙烯。
• Preparation of 4,4'-dihydroxy stilbenes or derivatives thereof
  申请人：MONSANTO COMPANY

  公开号：EP0001910A1

  公开（公告）日：1979-05-16

  Dehydrohalogenation-rearrangement of 1,1-bis (4-oxy-substituted aryl)-2- haloethanes to yield 4,4'-dioxy- substituted stiibenes is effected by heating an acidic reaction medium comprising the 1,1-bis (4-oxy- substituted aryl)-2- haloethana dissolved in a solution of an aliphatic carboxylic acid and a carboxylic acid salt The process is particularly directed to the preparation of 4,4'-dihydroxystilbene from 1,1-bis (4-hydroxyphenyl)- 2-chloroethane. The 4,4'-dihydroxystilbene may further be acylated to the diacyloxy derivative.

  1，1-双（4-氧代芳基）-2-卤代乙烷的脱氢卤化重排生成 4，4'-二氧代链烷烃的方法是加热酸性反应介质，该介质包括溶解在脂肪族羧酸和羧酸盐溶液中的 1、该工艺特别适用于从 1,1-双（4-羟基苯基）-2-氯乙烷制备 4,4'-二羟基二苯乙烯。4,4'-二羟基二苯乙烯可进一步酰化为二乙酰氧基衍生物。
• Direct Electrochemical Reduction of 4,4^′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide
  作者：Caitlyn M. McGuire、Dennis G. Peters

  DOI：10.1149/2.0921605jes

  日期：——

  Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the electrochemical reduction of 4,4'-(2,2,2-trichloroethane-1,1-diyl)bis(methoxybenzene), commonly known as the pesticide methoxychlor, at glassy carbon and silver cathodes in dimethylformamide (DMF) containing 0.050 M tetra-n-butylammonium tetrafluoroborate (TBABF(4)). Reduction of methoxychlor at both glassy carbon and silver shows four voltammetric peaks, the first three of which are associated with cleavage of carbon-chlorine bonds; the fourth peak is assigned to reduction of 4,4'-(ethene-1,1-diyl)bis(methoxybenzene). Bulk electrolyses of methoxychlor at reticulated vitreous carbon and silver mesh cathodes at potentials corresponding to each of the first three voltammetric peaks were conducted; coulometric n values and product distributions (determined by means of GC and GC-MS techniques) depend on potential. In particular, two completely dechlorinated products, namely 4,4'-(ethane-1,1-diyl)bis(methoxybenzene) and 4,4'-(ethene-1,1-diyl)bis(methoxybenzene) have been identified and quantitated. A mechanistic scheme is proposed to account for the formation of the various products. (C) The Author(s) 2016. Published by ECS. All rights reserved.