1,1-二苯基-1-庚烯 | 1530-20-7

• 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: 1,1-二苯基-1-庚烯
• 英文名称: 1,1-diphenyl-1-heptene
• 英文别名: hept-1-ene-1,1-diyldibenzene；1,1-Diphenyl-1-hepten；1,1-Diphenyl-hept-1-en；1,1-Diphenyl-hepten-1；1-phenylhept-1-enylbenzene
• CAS: 1530-20-7
• 化学式: C₁₉H₂₂
• 分子量: 250.384
• InChiKey: SRMGQBFDRIIXAH-UHFFFAOYSA-N

物化性质

• 沸点：
  353.51°C (estimate)
• 密度：
  0.9591

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  1,1-二苯基-1-庚烯 在 臭氧 作用下， 以 四氯化碳 为溶剂， 生成 1,1-diphenylheptene 1-ozonide
  参考文献：
  名称：

  Reaction of ozonide with antimony pentachloride or chlorosulfuric acid. Participation of antimony pentachloride-complexed or protonated carbonyl oxide

  摘要：

  DOI：

  10.1021/ja00521a045
• 作为产物：
  描述：

  7,7-diphenyl-2-methyl-6-heptenoic acid 2-thioxo-2H-pyridin-1-yl ester 在 苯硒酚 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到1,1-二苯基-1-庚烯
  参考文献：
  名称：

  Adjusting the Top End of the Alkyl Radical Kinetic Scale. Laser Flash Photolysis Calibrations of Fast Radical Clocks and Rate Constants for Reactions of Benzeneselenol

  摘要：

  Rate constants for 5-exo cyclizations of the 6,6-diphenyl-5-hexenyl radical (la), the 1-methyl-6,6-diphenyl-5-hexenyl radical (Ib), and the 1,1-dimethyl-6,6-diphenyl-5-hexenyl radical (Ic) were measured by laser flash photolysis methods, and Arrhenius parameters for these cyclizations were determined. Relative rate constants for cyclizations of radicals 1 and reactions with benzeneselenol were determined by indirect kinetic methods, and the relative Arrhenius parameters for the competing reactions were combined with the parameters for the cyclization reactions to give absolute Arrhenius parameters for the PhSeH reactions. At 20 degrees C, PhSeH reacts with the 1 degrees, 2 degrees, and 3 degrees radicals 1 with nearly the same rate constants, (1.2 +/- 0.1) x 10(9) M-1 s(-1). Absolute Arrhenius parameters for reactions of PhSH and t-BuSH with the primary alkyl radical la were calculated using literature values for the competition between cyclization of la and reactions with the appropriate thiol and the absolute values for cyclization of la determined in this work. The results suggest that rate constants for reactions of primary alkyl radicals with t-BuSH are about 20% smaller than those previously reported. In the case of PhSH, the results are in good agreement with one previously reported set of rate constants but about 35% smaller than another set of rate constants that was subsequently incorporated into fast alkyl radical kinetics. The rate constants for alkyl radical reactions calibrated by competition against reaction with PhSeH and PhSH apparently are 30-40% smaller than those previously reported, and the derived rate constants for the fast radical reactions should be adjusted. An especially noteworthy example is ring opening of the cyclopropylcarbinyl radical, the Arrhenius function for which was determined in part from PI ISH trapping results. Using the adjusted rate constants for PhSH and recalculating the Arrhenius parameters for the cyclopropylcarbinyl radical ring opening gives log(k/s(-1)) = (13.04(5) +/- 0.10) - (6.99 +/- 0.09)/theta (kcal/mol, errors at 2 sigma); the rate constant at 20 degrees C of 6.7 x 10(7) s(-1) is about 13% smaller than that previously calculated.

  DOI：

  10.1021/jo981930s

文献信息

• Alkene homologation <i>via</i> visible light promoted hydrophosphination using triphenylphosphonium triflate
  作者：Vitalij V. Levin、Alexander D. Dilman

  DOI：10.1039/d0cc07025d

  日期：——

  A hydrophosphination reaction of alkenes with triphenylphosphonium triflate under photocatalytic conditions is described. The reaction is promoted by naphthalene-fused N-acylbenzimidazole and is believed to proceed through intermediate formation of a phosphinyl radical cation. The resulting phosphonium salts are directly involved in the Wittig reaction leading to homologated alkenes.

  描述了在光催化条件下烯烃与三氟甲磺酸三苯基phosph的氢磷酸化反应。该反应由萘稠合的N-酰基苯并咪唑促进，并且据信通过膦酰基自由基阳离子的中间形成而进行。生成的phospho盐直接参与Wittig反应，从而生成同构的烯烃。
• Et₂Zn-Mediated Rearrangement of Bromohydrins
  作者：Lezhen Li、Peijie Cai、Qingxiang Guo、Song Xue

  DOI：10.1021/jo800231s

  日期：2008.5.1

  and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins

  描述了一种简单高效的方法，用于重排由Et 2 Zn介导的溴代醇以合成羰基化合物。用0.6当量的Et 2 Zn处理各种β-溴代醇，在CH 2 Cl 2中形成锌络合物在室温下反应2小时，然后进行1，2-迁移，得到相应的羰基化合物。对于无环和环状的溴代醇，这种显着且清洁的重排是普遍的，并且根据起始的溴代醇的特征，以良好或优异的收率获得了各种环膨胀和收缩的羰基化合物。该反应中有机锌试剂的官能团耐受性将用于有机合成中。还研究了这种重排过程的范围和局限性。
• Application of indium ate complexes to synthetic chemistry. Selective conjugate addition to enones and coupling with allylic halides
  作者：Shuki Araki、Toshio Shimizu、Shun-Ji Jin、Yasuo Butsugan

  DOI：10.1039/c39910000824

  日期：——

  Tetraorganoindium ate complexes, prepared by the addition of organolithium reagents to trialkylindium, reacted with α,β-unsaturated ketones in a 1,4-addition fashion; allylic indates derived from allylic indium sesquihalides coupled with allylic halides regio- and stereo-specifically to give high yields of head-to-tail 1,5-dienes.

  通过向三烷基铟中添加有机锂试剂制备的四有机铟盐配合物，与α，β-不饱和酮以1,4-加成方式反应；衍生自烯丙基倍半卤化铟与烯丙基卤化物在区域和立体上偶合的烯丙基吲哚，可产生高产率的头尾1，5-二烯。
• Nickel-Catalyzed Alkylative Cross-Coupling of Anisoles with Grignard Reagents via C–O Bond Activation
  作者：Mamoru Tobisu、Tsuyoshi Takahira、Toshifumi Morioka、Naoto Chatani

  DOI：10.1021/jacs.6b03253

  日期：2016.6.1

  We report nickel-catalyzed cross-coupling of methoxyarenes with alkylmagnesium halides, in which a methoxy group is eliminated. A wide range of alkyl groups, including those bearing β-hydrogens, can be introduced directly at the ipso position of anisole derivatives. We demonstrate that the robustness of a methoxy group allows this alkylation protocol to be used to synthesize elaborate molecules by

  我们报告了镍催化的甲氧基芳烃与烷基卤化镁的交叉偶联，其中甲氧基被消除。广泛的烷基，包括那些带有 β-氢的烷基，可以直接在苯甲醚衍生物的 ipso 位置引入。我们证明甲氧基的稳健性允许该烷基化方案通过将其与传统的交叉偶联反应或氧化转化相结合来合成复杂的分子。这种方法的成功取决于使用烷基碘化镁，而不是氯化物或溴化物，这突出了卤化物在使用格氏试剂进行催化反应中的重要性。
• Synthetic Radical Reactions Using Dibutylchlorogermane and ­Dibutylethoxygermane as Radical Mediators
  作者：Katsukiyo Miura、Akira Hosomi、Kazunori Ootsuka

  DOI：10.1055/s-2005-921927

  日期：——

  In the presence of Et3B as radical initiator, dibutylchlorogermane (1a) and dibutylethoxygermane (1b) reacted with bromo- and iodoalkanes at room temperature to give the corresponding alkanes in high yields. Hydrogermane 1a was more reactive than 1b. However, 1b worked as a better radical mediator in intermolecular radical addition of haloalkanes to electron-deficient alkenes.

  在三乙基硼作为自由基引发剂的存在下，二丁基氯锗烷（1a）和二丁基乙氧基锗烷（1b）在室温下与溴代和碘代烷烃反应，以高产率生成相应的烷烃。氢锗烷1a比1b更具反应活性。然而，1b在卤代烷烃与缺电子烯烃的分子间自由基加成反应中表现更佳的自由基媒介作用。