1-(2,2-dibromo-1,1-dimethoxyethyl)benzene | 33604-58-9

• 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-dibromo-1,1-dimethoxyethyl)benzene
• 英文别名: (2,2-Dibromo-1,1-dimethoxyethyl)benzene
• CAS: 33604-58-9
• 化学式: C₁₀H₁₂Br₂O₂
• 分子量: 324.012
• InChiKey: WPOLJTXVJCRRKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,2-dibromo-1,1-dimethoxyethyl)benzene 反应 12.0h， 以98%的产率得到2,2-二溴-1-苯乙酮
  参考文献：
  名称：

  Iron(III) catalyzed halo-functionalization of alkynes

  摘要：

  Aromatic and aliphatic alkynes can be halo-functionalized to alpha,alpha-dihalodimethyl ketals catalyzed by FeCl3 in excellent yields. MeOH is used as a nucleophilic solvent and N-halosuccinimide as the halogen source for this efficient transformation. The resulting alpha,alpha-dibromodimethyl ketals can be converted to the corresponding alpha,alpha-dibromoketones by treatment with 8% FeCl3 in silica gel. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.039
• 作为产物：
  描述：

  苯乙炔 以79%的产率得到
  参考文献：
  名称：

  UEMURA S.; OKAZAKI H.; OKANO M.; SAWADA S.; OKADA A.; KUWABARA K., BULL. CHEM. SOC. JAP., 1978, 51, NO 6, 1911-1912

  摘要：

  DOI：

文献信息

• Nucleophilic substitution at an acetylenic carbon
  作者：R. Tanaka、M. Rodgers、R. Simonaitis、S.I. Miller

  DOI：10.1016/s0040-4020(01)98055-x

  日期：1971.1

  detectable products, phenylacetylene, phenylmethoxyacetylene (2), (E)-β-bromo-β-methoxy- styrene, and (Z)-β-bromo-α-methoxystyrene lie on discrete mechanistic paths and are not interconvertible under the reaction conditions. Comparable amounts of alkynyl and alkenyl ethers are formed by attack on carbon 1. The element effects for attack on halogen, K(Cl)/k(Br) ⋍ 0·4, and on carbon 1, k(Cl)/L(Br) ⋍ 1·6 are

  苯卤代乙炔对甲醇中的甲醇离子是三亲的。在苯氯乙炔（1 '）的作用下，甲醇盐对氯的侵蚀程度约为0·2％，对碳1的侵蚀程度约为99％，对于碳2的侵蚀程度约为1％；与苯基溴乙炔（1）一起，甲醇盐对溴的攻击约为5％，对碳1的干扰为〜83％，对碳2的攻击为约11％。第一种可检测的产物为苯乙炔，苯甲氧基乙炔（2），（E）-β-溴-β -甲氧基-苯乙烯和（Z）-β-溴-α-甲氧基苯乙烯位于不连续的机理路径上，并且在反应条件下不可相互转化。相当数量的炔基和烯基醚是通过碳1的进攻而形成的。元素对卤素，K（Cl）/ k（Br）⋍0·4和对碳1的进攻。k（Cl）/ L（Br）⋍1·6与独立竞争过程的概念一致。苯甲氧基乙炔是短寿命的瞬态。它的形成和衰变（含甲醇盐）的速率常数，在78°弧时k 1'2（Cl）0·6×10 -4 *或k 12（Br）0·5×10 -4和K j 1·7×10 -3 M -1秒-1。以前，
• Solvent Incorporation in Bromination of Acetylenes in Alcohols
  作者：Sakae Uemura、Hajime Okazaki、Masaya Okano、Seiji Sawada、Atsuko Okada、Kimiko Kuwabara

  DOI：10.1246/bcsj.51.1911

  日期：1978.6

  The reactions of acetylenes with bromine in alcohols at 20–25 °C afford dibromodialkoxyalkanes in good yields together with variable amounts of dibromoalkenes. Similar treatment of phenylacetylene with copper(II) bromide gives only bromophenylacetylene and 2-phenyl-1,1,2-tribromoethylene, the latter being formed by dibromination of the former with copper(II) bromide.

  乙炔与溴在 20-25 °C 的醇中反应以良好的收率提供二溴二烷氧基烷烃和不同数量的二溴烯烃。用溴化铜 (II) 对苯乙炔进行类似处理，仅得到溴苯乙炔和 2-苯基-1,1,2-三溴乙烯，后者通过前者与溴化铜 (II) 的二溴化反应形成。
• Facile generation of α,α-dibromodimethyl ketals from alkynes using TsNBr2
  作者：Kamal Krishna Rajbongshi、Prodeep Phukan

  DOI：10.1016/j.tetlet.2014.01.123

  日期：2014.3

  TsNBr2 reacts with alkyne in the presence of methanol to form alpha,alpha-dibromodimethyl ketals instantaneously. The reaction proceeds smoothly at room temperature without using any other catalyst. The one step reaction can be carried out with both aromatic and aliphatic alkynes in excellent yield. (C) 2014 Elsevier Ltd. All rights reserved.
• Solvent Incorporation in Bromination of Alkynes With Tetrabutylammonium Tribromide in Methanol
  作者：Berthelot, Jacques、Benammar, Yamina、Desmazieres, Bernard

  DOI：10.1080/00397919708004163

  日期：1997.8

  The reaction of tetrabutylammonium tribromide (TBABr(3)) with mono and disubstituted alkynes in methanol at 20 degrees C leads to the formation of mainly the corresponding alpha,alpha-dibromo, beta,beta-dimethoxyalkane and the E-(alpha,beta)-dibromoalkene. The additions are faster using sonication.
• Facile formations of ketals of α, α-dihaloacetophenones
  作者：Pakorn Bovonsombat、Edward McNelis

  DOI：10.1016/s0040-4039(00)74668-5

  日期：1992.7

  Ketals of alpha, alpha-dihaloacetophenones are prepared in high yields from phenylethyne and N-halosuccinimide with catalytic quantities of p-toluenesulfonic acid.