1-(1-bromo-3,3,3-trichloro-propyl)-4-chloro-benzene | 511533-74-7

• 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-(1-bromo-3,3,3-trichloro-propyl)-4-chloro-benzene
• 英文别名: 1-(1-Brom-3,3,3-trichlor-propyl)-4-chlor-benzol；1-(1-Bromo-3,3,3-trichloropropyl)-4-chlorobenzene
• CAS: 511533-74-7
• 化学式: C₉H₇BrCl₄
• 分子量: 336.871
• InChiKey: VHLCNMKMQQVDED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-(1-bromo-3,3,3-trichloro-propyl)-4-chloro-benzene 、 异丁烯 在 potassium tert-butylate 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以42%的产率得到1-Chloro-4-(1-chloro-2,2-dimethyl-cyclopropylethynyl)-benzene
  参考文献：
  名称：

  摘要：

  When treated with KOH under phase-transfer catalysis or with (BuOK)-O-t, 3-substituted (alkyl or phenyl) 1, 1, 3-tribromo-1-fluoropropanes 1a-c exclusively generate previously unknown (alk-1-ynyl)fluorocarbenes 5a-c, which react with olefins to give 1-(alk-1-ynyl)-1-fluorocyclopropanes 6a-h in 12-69% yields. Under analogous conditions, 3-alkyl- and 3-aryl-3-bromo-1, 1, 1-trichloropropanes 2a-c selectively afford (alk-1-ynyl)chlorocarbenes 7a-c, which are trapped by olefins to form the corresponding 1-(alk-1-ynyl)-1-chlorocyclopropanes 8a-k in 35-70% yields. (Phenylethynyl)chlorocarbene 7a is also selectively generated from 1, 1, 1, 3-tetrachloro-3-phenylpropane (3a) upon its treatment with (BuOK)-O-t. With an excess of 2,3-dimethylbut-2-ene or 2-methylpropene, carbene 7a yields 1-chloro-1-(phenylethynyl)cyclopropanes 8a or 8c, respectively. In contrast, 1, 1, 1, 3-tetrachloroheptane 3b and 3-alkyl- and 3-phenyl-1, 1, 1, 3-tetrabromopropanes 4a,c,f react with bases in the presence of olefins to give, along with the corresponding 1-(alk-1-ynyl)-1-halocyclopropanes 8a,c,d and 11a-f, vinylidenecyclopropanes 12a,c-g, which suggests the generation, under these conditions; both (alk-1-ynyl)halocarbenes 7b and 9a-c and vinylidenecarbenes 10 and 11a-c. The composition and structures of intermediate products in the reactions of tetrahalides 1b, 2a, 2b, 3a, and 3b with (BuOK)-O-t were determined and the mechanisms for carbene generation in these reactions were proposed.

  DOI：

  10.1023/a:1020952513679
• 作为产物：
  描述：

  4-氯苯乙烯 、 三氯溴甲烷 在 偶氮二异丁腈 作用下， 生成 1-(1-bromo-3,3,3-trichloro-propyl)-4-chloro-benzene
  参考文献：
  名称：

  摘要：

  When treated with KOH under phase-transfer catalysis or with (BuOK)-O-t, 3-substituted (alkyl or phenyl) 1, 1, 3-tribromo-1-fluoropropanes 1a-c exclusively generate previously unknown (alk-1-ynyl)fluorocarbenes 5a-c, which react with olefins to give 1-(alk-1-ynyl)-1-fluorocyclopropanes 6a-h in 12-69% yields. Under analogous conditions, 3-alkyl- and 3-aryl-3-bromo-1, 1, 1-trichloropropanes 2a-c selectively afford (alk-1-ynyl)chlorocarbenes 7a-c, which are trapped by olefins to form the corresponding 1-(alk-1-ynyl)-1-chlorocyclopropanes 8a-k in 35-70% yields. (Phenylethynyl)chlorocarbene 7a is also selectively generated from 1, 1, 1, 3-tetrachloro-3-phenylpropane (3a) upon its treatment with (BuOK)-O-t. With an excess of 2,3-dimethylbut-2-ene or 2-methylpropene, carbene 7a yields 1-chloro-1-(phenylethynyl)cyclopropanes 8a or 8c, respectively. In contrast, 1, 1, 1, 3-tetrachloroheptane 3b and 3-alkyl- and 3-phenyl-1, 1, 1, 3-tetrabromopropanes 4a,c,f react with bases in the presence of olefins to give, along with the corresponding 1-(alk-1-ynyl)-1-halocyclopropanes 8a,c,d and 11a-f, vinylidenecyclopropanes 12a,c-g, which suggests the generation, under these conditions; both (alk-1-ynyl)halocarbenes 7b and 9a-c and vinylidenecarbenes 10 and 11a-c. The composition and structures of intermediate products in the reactions of tetrahalides 1b, 2a, 2b, 3a, and 3b with (BuOK)-O-t were determined and the mechanisms for carbene generation in these reactions were proposed.

  DOI：

  10.1023/a:1020952513679

文献信息

• Effect of sodium acetate in atom transfer radical addition of polyhaloalkanes to olefins
  作者：Yoshinari Sawama、Ryosuke Nakatani、Takahiro Imanishi、Yuta Fujiwara、Yasunari Monguchi、Hironao Sajiki

  DOI：10.1039/c3ra47457g

  日期：——

  The atom transfer radical addition of polyhaloalkanes, such as bromotrichloromethane and polyfluoroalkyl iodine, to olefins smoothly proceeds in the presence of sodium acetate as an efficient auxiliary agent in dimethoxyethane. The present transition metal- and peroxide-free methodology is applicable to a broad scope of substrates.

  在作为二甲氧基乙烷中有效助剂的乙酸钠的存在下，将多卤代烷烃如溴代三氯甲烷和多氟烷基碘的原子转移自由基加成至烯烃。当前的无过渡金属和无过氧化物的方法学适用于广泛的基材。
• THE CHEMISTRY OF HYDROPEROXIDES. XII. THE GENERATION AND PROPERTIES OF FREE RO₂. RADICALS
  作者：M. S. KHARASCH、PETER PAUSON、WALTER NUDENBERG

  DOI：10.1021/jo01131a016

  日期：1953.3