exo-2-(trichloromethyl)-endo-3-chlorobicyclo[2.2.1]heptane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: exo-2-(trichloromethyl)-endo-3-chlorobicyclo[2.2.1]heptane
• 英文别名: (1S,2S,3S,4R)-2-chloro-3-(trichloromethyl)bicyclo[2.2.1]heptane
• 化学式: C₈H₁₀Cl₄
• 分子量: 247.979
• InChiKey: UBXTVVBTCPESJI-BWBBJGPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  四氯化碳 、 norbornene 在 ruthenium(II) bis(triphenylphosphine) dichloride 作用下， 以 苯 为溶剂， 反应 24.0h， 以61%的产率得到exo-2-(trichloromethyl)-endo-3-chlorobicyclo[2.2.1]heptane
  参考文献：
  名称：

  Exploring the Substrate Scope of the Ru(II)-Catalyzed Kharasch Reaction

  摘要：

  Kharasch反应，或者说卤代烷烃与烯烃的原子转移加成反应，已知可以由多种Ru(II)配合物催化。易于制备的[RuCl₂(PPh₃)₃]被用来研究反应的范围。许多卤代烷烃被加到一系列烯烃中，具有良好到优秀的区域选择性。

  DOI：

  10.1135/cccc20071005

文献信息

• Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts
  作者：Carl-Johan Wallentin、John D. Nguyen、Peter Finkbeiner、Corey R. J. Stephenson

  DOI：10.1021/ja300798k

  日期：2012.5.30

  visible light-mediated atom transfer radical addition (ATRA) of haloalkanes onto alkenes and alkynes using the reductive and oxidative quenching of [IrdF(CF(3))ppy}(2)(dtbbpy)]PF(6) and [Ru(bpy)(3)]Cl(2) is presented. Initial investigations indicated that the oxidative quenching of photocatalysts could effectively be utilized for ATRA, and since that report, the protocol has been expanded by broadening

  在此，使用 [IrdF(CF(3))ppy}(2)(dtbbpy)]PF( 6) 和 [Ru(bpy)(3)]Cl(2)。初步调查表明，光催化剂的氧化猝灭可以有效地用于 ATRA，自该报告以来，该协议通过扩大光催化剂、底物和溶剂方面的反应范围进行了扩展。此外，进一步修改反应条件允许使用 [Ru(bpy)(3)]Cl(2) 和抗坏血酸钠作为牺牲电子供体的还原淬火循环，将全氟烷基碘化物有效地 ATRA 转化为烯烃和炔烃。
• Ruthenium(<scp>II</scp>)- and rhenium(<scp>III</scp>)-catalysed addition of tetrahalogenomethanes to alkenes and 1,ω-dienes. Stereoselective formation of cis-1,2-disubstituted cyclopentanes from 1,6-dienes
  作者：Ronald Grigg、John Devlin、Ashok Ramasubbu、Ronald M. Scott、Paul Stevenson

  DOI：10.1039/p19870001515

  日期：——

  Acetonitrile(trichloro)bis(triphenylphosphine)rhenium(III) is found to act as an initiator for the addition of carbon tetrachloride and bromotrichloromethane to terminal alkenes and dienes. Moderate to good yields of mono- and bis-adducts are obtained. 1,6-Dienes undergo a stereoselective addition-cyclization process with both the ReIII catalyst and with dichlorotris(triphenylphosphine)ruthenium (II) to give mixtures

  发现乙腈（三氯）双（三苯基膦）r（III）充当引发剂，用于将四氯化碳和溴三氯甲烷添加到末端烯烃和二烯中。获得了中等至良好的单加合物和双加合物的收率。1,6-二烯与Re III催化剂和二氯三（三苯基膦）钌（II）一起经历立体选择性加成环化过程，得到顺式和反式-3-卤代甲基-4（2,2,2-三氯乙基）的混合物顺式异构体占主导地位的环戊烷。讨论了立体选择性，并提供了有关Re III复合物作为简单引发剂的证据。
• Application of copper(I) halides to modifying reactivity of polyhalomethanes and arenesulfonyl chlorides in free-radical addition. “Cross-halogenation” reaction
  作者：A. S. Dneprovskii、A. N. Kasatochkin、V. P. Boyarskii、A. A. Ermoshkin、A. A. Yakovlev

  DOI：10.1134/s1070428006080033

  日期：2006.8

  In the free-radical addition of a number of organohalogen reagents to cyclic alkenes and dienes in the presence of copper(I) halides the composition of the reaction products is governed by the stage of a fast halogen transfer from the copper derivative to the alkyl radical. Under these conditions in contrast to the free-radical addition reactions initiated by UV light or peroxide initiators the intramolecular rearrangements are suppressed, the stereoselectivity of the reaction changes, and also some adducts contain halogen atoms different from those present in the organohalogen reagent employed.
• Khusnutdinov; Shchadneva; Baiguzina, Petroleum Chemistry, 2004, vol. 44, # 5, p. 350 - 357
  作者：Khusnutdinov、Shchadneva、Baiguzina、Lavrent'eva、Burangulova、Atnabaeva、Dzhemilev

  DOI：——

  日期：——
• Transition Metal-Catalyzed Hydroboration of and CCl₄ Addition to Alkenes
  作者：Schubert Pereira、Morris Srebnik

  DOI：10.1021/ja952653z

  日期：1996.1.1