羟基-环戊基-二苯基-甲烷 | 4479-29-2

• 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: 羟基-环戊基-二苯基-甲烷
• 英文名称: Hydroxy-cyclopentyl-diphenyl-methan
• 英文别名: Cyclopentyl-diphenyl-methanol；Cyclopentyl-diphenyl-carbinol；Cyclopentyl(diphenyl)methanol
• CAS: 4479-29-2
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: RDZWIDDIURRCNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  羟基-环戊基-二苯基-甲烷 在 硫酸 作用下， 生成 (cyclopentyl-diphenyl-methyl)-methyl ether
  参考文献：
  名称：

  Ziegler et al., Justus Liebigs Annalen der Chemie, 1942, vol. 551, p. 150,186

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊基甲酰氯 、 苯基溴化镁 以 乙醚 为溶剂， 生成 羟基-环戊基-二苯基-甲烷
  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

• A Method for Synthesis of Homoallylic Bromide
  作者：Wenke Qi、Peipei Wang、Liyuan Fan、Songlin Zhang

  DOI：10.1021/jo400580n

  日期：2013.6.21

  Cyclopropyl Grignard reagents react with carbonyl compounds in the presence of diethyl phosphite to give homoallylic bromides. The reaction is effectively carried out under mild conditions in a one-pot fashion with moderate to good yields.

  环丙基格氏试剂在亚磷酸二乙酯的存在下与羰基化合物反应生成均烯丙基溴化物。该反应在温和条件下以一锅法有效地进行，产率中等至良好。
• Hydrocarbon Activation. Synthesis of β-Cycloalkyl (Di)nitriles through Photosensitized Conjugate Radical Addition
  作者：Anna Maria Cardarelli、Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1021/jo010400k

  日期：2001.11.1

  Photoinduced hydrogen abstraction from aliphatic cyclic hydrocarbons (C(5) to C(7), C(12), as well as adamantane) by triplet aromatic ketones in the presence of alpha,beta-unsaturated (di)nitriles offers a straightforward entry to the corresponding alkylated (di)nitriles via the alkyl radicals. Yields are moderate to good depending on the olefins structure (substitution in beta slows down the addition

  在存在α，β-不饱和（di）腈的情况下通过三重芳族酮从脂肪族环状烃（C（5）到C（7），C（12）以及金刚烷）的光诱导氢提取提供了直接的途径经由烷基的相应的烷基化的（二）腈。取决于烯烃的结构，产率中等至良好（β取代会减慢单腈的加成，但对于α，α-二腈，电子活化也可使β，β-二取代底物有效烷基化）。用（1-甲基戊-4-烯叉）丙二腈获得了串联烷基化-环化方法。
• NBS-Promoted Rearrangement of 1,1-Diarylmethylenecyclopentane
  作者：Meng-Yang Chang、Chung-Han Lin

  DOI：10.1002/jccs.201190135

  日期：2011.12

  AbstractThe 1‐aroyl‐1‐aryl‐2‐bromocyclopentanes 3a, 3b, 3c and 3d (Ar = C6H5, 2‐FC6H4, 3‐FC6H4, 4‐FC6H4) were prepared from N‐bromosuccinimide (NBS)‐promoted rearrangement of 1,1‐diarylmethylenecyclopentane 2. The possible mechanism was proposed. Two 1‐phenyl‐cyclopentane carbamides 5a and 5b with the anti‐influenza effect were also accomplished from compound 3a.
• Kasansski; Tatewossjan, Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1428,1433
  作者：Kasansski、Tatewossjan

  DOI：——

  日期：——
• Nametkin; Wolodina, Zhurnal Obshchei Khimii, 1948, vol. 18, p. 2033,2034
  作者：Nametkin、Wolodina

  DOI：——

  日期：——