(1-溴-3,3,3-三氯丙基)苯 | 34372-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1-溴-3,3,3-三氯丙基)苯
• 英文名称: (1-bromo-3,3,3-trichloropropyl)benzene
• 英文别名: 1-bromo-1-phenyl-3,3,3-trichloropropane；3-bromo-1,1,1-trichloro-3-phenylpropane；3-bromo-3-phenyl-1,1,1-trichloropropane；(1-bromo-3,3,3-trichloro-propyl)-benzene；(1-Brom-3,3,3-trichlor-propyl)-benzol；<3-Trichlor-1-brom-propyl>-benzol
• CAS: 34372-27-5
• 化学式: C₉H₈BrCl₃
• 分子量: 302.426
• InChiKey: GYXDKVQPLSJHKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  54.5-55 °C
• 沸点：
  92 °C(Press: 0.2 Torr)
• 密度：
  1.618±0.06 g/cm3(Predicted)
• 保留指数：
  1618

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 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-溴-3,3,3-三氯丙基)苯 在 三乙胺 作用下， 反应 8.0h， 以28%的产率得到1,1,3-trichloro-3-phenylprop-1-ene
  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：

  苯乙烯 、 三氯溴甲烷 在 [{RhCl(η⁴-cod)}2(μ-THDP)] 十一烷 、 三乙胺 作用下， 以 水 为溶剂， 反应 44.0h， 以88%的产率得到(1-溴-3,3,3-三氯丙基)苯
  参考文献：
  名称：

  在水性介质中开发 Kharasch 反应：包含桥笼配体三（1,2-二甲基肼）二膦的双核第 8 和第 9 族催化剂

  摘要：

  双核配合物 [{RuCl2(η6-p-cymene)}2(μ-THDP)] (4) 和 [{MCl(η4-cod)}2(μ-THDP)] [M = Rh (5), Ir (6)] 含有桥笼型配体三（1,2-二甲基肼基）二膦（THDP），通过处理二聚体 [{RuCl(μ-Cl)( η6-p-cymene)}2] (1) 和 [{M(μ-Cl)(η4-cod)}2] [M = Rh (2), Ir (3)] 与一当量的 THDP。(η6-芳烃)钌(II)衍生物4的结构已经通过X射线衍射方法明确证实。已发现所有这些配合物都是在温和条件（室温）下，在非均相水性介质中，溴三氯甲烷与烯烃的原子转移自由基加成反应（Kharasch 反应）的活性催化剂。（© Wiley-VCH Verlag GmbH & Co. KGaA， 69451 魏因海姆，德国，2008）

  DOI：

  10.1002/ejic.200701132

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。
• Development of an indicator for the direct visualization of radical intermediates in organic reactions
  作者：Qiuli Yao、Chao-Jun Li

  DOI：10.1039/c7cc05977a

  日期：——

  A color-indicator based on a derivative of rhodamine amide was developed for the detection of radical intermediates in organic reactions. This derivative showed sensitive color changes for various radical intermediates initiated by chemical reagents or UV light.

  开发了基于若丹明酰胺衍生物的颜色指示剂，用于检测有机反应中的自由基中间体。对于由化学试剂或紫外线引发的各种自由基中间体，该衍生物显示出敏感的颜色变化。
• Dinuclear Palladium(III) Complexes with a Single Unsupported Bridging Halide Ligand: Reversible Formation from Mononuclear Palladium(II) or Palladium(IV) Precursors
  作者：Julia R. Khusnutdinova、Nigam P. Rath、Liviu M. Mirica

  DOI：10.1002/anie.201100928

  日期：2011.6.6

  Stable PdIII: Dinuclear PdIII complexes of the tridentate ligand trimethyltriazacyclononane (Me3tacn) were obtained by one‐electron oxidation of mononuclear PdII precursors. Further oxidation led reversibly to mononuclear PdIV species. The PdII and PdIII complexes are shown to be involved in the catalytic Kharasch addition of polyhaloalkanes to alkenes.

  稳定的Pd III：通过单核Pd II前体的单电子氧化获得三齿配体三甲基三氮杂环壬烷（Me 3 tacn）的双核Pd III配合物。进一步的氧化可逆地导致了单核Pd IV物种。Pd II和Pd III络合物显示参与多卤代烷烃向烯烃的催化Kharasch加成反应。
• Alkynylhalocarbenes
  作者：K. N. Shavrin、V. D. Gvozdev、O. M. Nefedov

  DOI：10.1007/bf02503489

  日期：1998.6

  (Alk-1-ynyl)chlorocarbenes (3), generated from 1,1-dihaloalk-2-ynes and 3-substituted 3-bromo-1,1,1-trichloropropanes under the action of (BuOK)-O-t in THF at 20 degrees C, react with excess alkali metal alkoxide 4 to give 3-substituted 2-(alk-1-ynyl)oxiranes (6) in 26-78%; yields, most likely as a result of insertion of carbene 3 into the alpha C-H bond of alkoxides 4 and subsequent cyclization of the resulting 1-substituted 2-chloro-2-(alk-1-ynyl)etoxides. The yields of oxiranes 6 depend on the nature of the alkali metal used to prepare alkoxides 4 and on the method employed for the preparation of the latter.

  (丙-1-炔基)氯卡宾(3)由1,1-二卤代丙-2-炔与3-取代的3-溴-1,1,1-三氯丙烷，通过在四氢呋喃中用丁基氧化钾-O-t加热至20℃，与过量的碱金属烷基氧化物4反应，得到的产率为26-78%的3-取代的2-(丙-1-炔基)环氧乙烷(6)。产率的变化很可能是由于氯卡宾3插入到烷基氧化物4的α-C-H键，随后发生环化反应生成1-取代的2-氯-2-(丙-1-炔基)乙基氧化物所致。环氧乙烷6的产率依赖于制备烷基氧化物4时所用的碱金属种类以及制备方法。
• On the Reaction of α-Chlorocarbenium Ions with Sulfinylamines
  作者：André Voges、Atef Hamed、Amal Ahmed El-Badry、Abdel-Hamid Ismail、Johannes C. Jochims

  DOI：10.1055/s-1995-3902

  日期：1995.3

  Aryl-, and vinyltrichloromethanes 1 are transformed with antimony pentachloride to α,α-dichlorocarbenium salts 2, which react with sulfinylamines 3 to afford nitrilium salts 4 in good yields. In contrast to this preparatively useful reaction, the reaction of α-monochlorocarbenium ions 8 (obtained from diaryldichloromethanes 7) with sulfinylamines 3 affords mixtures of iminium salts 10, isoindolium salts 13, and 2-azoniaallene salts 14.

  芳基三氯甲烷和乙烯基三氯甲烷 1 用五氯化锑转化为 α,α-二氯碳鎓盐 2，其与亚磺酰胺 3 反应，以良好的产率提供硝基鎓盐 4。与此制备有用的反应相反，α-一氯碳鎓离子 8（从二芳基二氯甲烷 7 获得）与亚磺胺 3 的反应提供亚胺盐 10、异吲哚盐 13 和 2-azoniaallen 盐 14 的混合物。