(2-butylcyclopropane-1,1-diyl)dibenzene | 133636-48-3

• 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: (2-butylcyclopropane-1,1-diyl)dibenzene
• 英文别名: 1-n-butyl-2,2-diphenylcyclopropane；1,1-diphenyl-2-butylcyclopropane；(2-Butyl-1-phenylcyclopropyl)benzene
• CAS: 133636-48-3
• 化学式: C₁₉H₂₂
• 分子量: 250.384
• InChiKey: UGPCZNLKEYANIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  348.6±12.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  二苯基重氮甲烷 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 (2-butylcyclopropane-1,1-diyl)dibenzene
  参考文献：
  名称：

  双（N-杂环卡宾）负载的二苯基重氮甲烷和镍的1-叠氮金刚烷配合物的合成，结构和催化反应性

  摘要：

  用Ni（NHC）二苯基重氮甲烷进行反应2（1，NHC =  Ñ -杂环卡宾），得到式（NHC）的复合物2的Ni（κ 1 -N 2器CPh 2）（3），其中配体重氮烷结合到金属在最终上κ 1的方式。另外，1-IMES（IMES = 1,3-双（2,4,6-三甲基苯基）咪唑-2-亚基）与1- azidoadamantane发生反应（N 3 AD）以产生（IMES）2的Ni（η 2 -N 3 AD）（4），其中所述叠氮化物配体结合到所述金属中的一侧结合的η 2-时尚。虽然热解的3和4不诱导Ñ 2损失，以形成终端卡宾和imidos分别（IMES）2的Ni（κ 1 -N 2器CPh 2）（3-IMES）反应与烯烃在升高的温度下，得到的环丙烷的产品高产。或者3-IMES或1-IMES二苯基重氮甲烷与烯烃比为1：也可以与1进行催化该反应。提出了烯烃活化机理来解释环丙烷化反应。

  DOI：

  10.1016/j.jorganchem.2016.03.031

文献信息

• Copper(I)-Catalyzed Carbometalation of Nonfunctionalized Cyclopropenes Using Organozinc and Grignard Reagents
  作者：Kohei Endo、Takeo Nakano、Yutaka Ukaji

  DOI：10.1055/s-0034-1379959

  日期：——

  A highly efficient method was developed for the copper(I)-catalyzed carbometalation of various nonfunctionalized and functionalized cyclopropenes. Electrophilic trapping of the cyclopropylmetal intermediates gave multifunctionalized cyclopropanes.

  开发了一种高效的方法，用于铜 (I) 催化的各种非官能化和官能化环丙烯的碳金属化。环丙基金属中间体的亲电捕获得到多功能环丙烷。
• Oxiranylidene intermediate in the reaction of trans-2-chloro-3- tert-butyloxirane with sodium phenoxide.
  作者：Harlan L. Goering、Steven D. Paisley

  DOI：10.1016/s0040-4039(00)84962-x

  日期：1986.1

  The reaction of trans-2-chloro-3-(t-butyl)oxirane with sodium phenoxide in acetonitrile to give trans-2-phenoxy-3-(t-butyl)oxirane involves α-elimination to give an oxiranylidene which undergoes a stereoselective stepwise addition of phenol to give product.

  的反应反式-2-氯-3-（叔丁基）环氧乙烷与苯酚钠的乙腈溶液，得到反式-2-苯氧基-3-（叔丁基）环氧乙烷涉及α-消除，得到经历立体选择性的oxiranylidene逐步加入苯酚得到产物。
• Palladium carbene cluster: synthesis, structure and reactivity
  作者：Tatyana A Stromnova、Irina N. Busygina、Dmitry I Kochubey、Ilya I. Moiseev

  DOI：10.1016/0022-328x(91)80173-h

  日期：1991.10

  inner-sphere oxidation of carbene or carbonyl ligands during which an oxygen atom is transferred from the carboxylate group to the carbene or carbonyl ligand. Thermolysis of carbonyl clusters in benzene or toluene solutions gives rise to the products of CO2 insertion into the CH bond of the solvent forming benzoic acid from benzene and a mixture of phenylacetic and tolyl acids from toluene.

  第一钯碳烯簇，μ -四（diphenylmethyliden）-μ-tetraacetato的Quadro-tetrapalladium（4PD-PD）的Pd 4（μ-器CPh 2）4（μ-OAC）4（I），已被取代合成μ-四（羰基）-μ-四乙酰基-四氢四钯（4Pd-Pd）Pd 4（μ-CO）4（μ-OAc）4中的CO基二苯卡宾配体（II）并具有EXAFS数据的特征。讨论了I，II和相关簇的反应性。已经发现簇的热解涉及卡宾或羰基配体的内球氧化，在此期间，氧原子从羧酸根基团转移至卡宾或羰基配体。苯或甲苯溶液中羰基簇的热解产生了CO 2插入到溶剂的CH键中的产物，该溶剂由苯形成苯甲酸，由苯乙酸和甲苯酸的混合物从甲苯中形成。
• Discrete Bridging and Terminal Copper Carbenes in Copper-Catalyzed Cyclopropanation
  作者：Xuliang Dai、Timothy H. Warren

  DOI：10.1021/ja047935q

  日期：2004.8.1

  The Cu(I) beta-diketiminate [Me2NN]Cu(eta(2)-ethylene) (2) catalyzes the cyclopropanation of styrene with N2CPh2 to give 1,1,2-triphenylcyclopropane in 67% yield. Addition of N2CPh2 to 2 equiv of 2 allows for the isolation of the dicopper carbene [Me2NN]Cu}(2)(mu-CPh2) (3) in which the diphenylcarbene moiety is symmetrically bound between two [Me2NN]Cu fragments (Cu-C = 1.922(4) and 1.930(4) Angstrom) with a Cu-Cu separation of 2.4635(7) Angstrom. In toluene-d(8) solution, 3 reversibly dissociates a [Me2NN]Cu fragment to give [Me2NN]Cu(toluene) and the terminal carbene [Me2NN]Cu=CPh2. Dicopper carbene 3 reacts with 3 equiv of styrene to give 1,1,2-triphenylcyclopropane and 2 equiv of [Me2NN]Cu(eta(2)-styrene) within minutes. DFT studies with simplified ligands indicate a stronger Cu-C pi-back-bonding interaction from two Cu(I) centers to the carbene acceptor orbital in a dicopper carbene than that present in a monocopper carbene. Nonetheless, the terminal carbene [Me3NN]Cu=CPh2 (8) that possesses a p-methyl group on each beta-diketiminato N-aryl ring may be isolated and exhibits a shortened Cu-C distance of 1.834(3) Angstrom. The stoichiometric cyclopropanation of styrene by 8 in 1,4-dioxane is first-order in both copper carbene 8 and styrene with activation parameters DeltaH(not similar or equal to) = 10.4(3) kcal/mol and DeltaS(not similar or equal to) = -32.3(9) cal/mol-K. In 1,4-dioxane, 8 decomposes to Ph2C=CPh2 via first-order kinetics with activation parameters DeltaH(not similar or equal to) = 21(1) kcal/mol and DeltaS(not similar or equal to) = -8(3) cal/mol-K. Arene solutions of thermally sensitive terminal carbene 8 decompose to [Me3NN]-Cu(arene), which reacts with 8 still present in solution to give the more thermally stable [Me3NN]Cu}(2)-(mu-CPh2).
• Synthesis, structures, and catalytic reactivity of bis(N-heterocyclic carbene) supported diphenyldiazomethane and 1-azidoadamantane complexes of nickel
  作者：Nicole D. Harrold、Amanda R. Corcos、Gregory L. Hillhouse

  DOI：10.1016/j.jorganchem.2016.03.031

  日期：2016.7

  the metal in a side-bound η2-fashion. While thermolysis of 3 and 4 does not induce N2 loss to form terminal carbenes and imidos, respectively, (IMes)2Ni(κ1-N2CPh2) (3-IMes) reacts with olefins at elevated temperatures to give cyclopropane products in excellent yields. Either 3-IMes or 1-IMes can also perform this reaction catalytically with a 1:1 ratio of diphenyldiazomethane to olefin. An olefin activation

  用Ni（NHC）二苯基重氮甲烷进行反应2（1，NHC =  Ñ -杂环卡宾），得到式（NHC）的复合物2的Ni（κ 1 -N 2器CPh 2）（3），其中配体重氮烷结合到金属在最终上κ 1的方式。另外，1-IMES（IMES = 1,3-双（2,4,6-三甲基苯基）咪唑-2-亚基）与1- azidoadamantane发生反应（N 3 AD）以产生（IMES）2的Ni（η 2 -N 3 AD）（4），其中所述叠氮化物配体结合到所述金属中的一侧结合的η 2-时尚。虽然热解的3和4不诱导Ñ 2损失，以形成终端卡宾和imidos分别（IMES）2的Ni（κ 1 -N 2器CPh 2）（3-IMES）反应与烯烃在升高的温度下，得到的环丙烷的产品高产。或者3-IMES或1-IMES二苯基重氮甲烷与烯烃比为1：也可以与1进行催化该反应。提出了烯烃活化机理来解释环丙烷化反应。