1,1-diphenyl-1-hydroxy<2,2,2-2H3>ethane | 142868-82-4

• 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: 1,1-diphenyl-1-hydroxy<2,2,2-2H3>ethane
• 英文别名: 1,1-diphenyl[2,2,2-²H3]ethanol；2,2,2-trideuterio-1,1-diphenyl-ethanol；1,2-Diphenyl-(2,2,2-D3)-aethanol；2,2,2-Trideuterio-1,1-diphenylethanol
• CAS: 142868-82-4
• 化学式: C₁₄H₁₄O
• 分子量: 201.241
• InChiKey: GIMDPFBLSKQRNP-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1,1-diphenyl-1-hydroxy<2,2,2-2H3>ethane 在 高氯酸 作用下， 以 水 、 乙腈 为溶剂， 生成 (ethene-1,1-diyl-2,2-d2)dibenzene
  参考文献：
  名称：

  动力学氘同位素效应作为 1,1-二苯乙基氯的溶剂分解和取代反应中常见离子对中间体的证据

  摘要：

  1,1-二苯基-1-氯乙烷 (1-Cl) 在 25 o C 下在乙腈中的溶剂分解提供消除产物 1,1-二苯基乙烯 (3)。向乙腈中加入水或甲醇可提高消除速率并产生第二个产物 1,1-二苯基-1-羟基乙烷 (1-OH) 或 1,1-二苯基-1-甲氧基乙烷 (1-OMe) . 氘代类似物 1,1-二苯基-1-氯[2,2,2-2 H3]乙烷 (d-1-Cl) 反应较慢

  DOI：

  10.1021/ja00045a010
• 作为产物：
  描述：

  苯乙酮 在 重水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 1,1-diphenyl-1-hydroxy<2,2,2-2H3>ethane
  参考文献：
  名称：

  在中性条件下由酮和有机硼试剂在镍催化下直接合成芳基烯烃

  摘要：

  镍催化的芳基硼试剂与酮的加成直接产生芳基烯烃。中性条件允许存在醇类、酚类和丙二酸酯的酸性质子，并且还可以容忍脆弱的结构。

  DOI：

  10.1021/jacs.7b02742

文献信息

• Deuterium kinetic isotope effects in homogeneous decatungstate catalyzed photooxygenation of 1,1-diphenylethane and 9-methyl-9H-fluorene: evidence for a hydrogen abstraction mechanism
  作者：Ioannis N. Lykakis、Michael Orfanopoulos

  DOI：10.1016/j.tetlet.2005.09.017

  日期：2005.11

  decatungstate W10O324- catalyzed photooxygenation of 1,1-diphenylethane and 9-methyl-9H-fluorene has been studied mechanistically. The primary and β-secondary kinetic isotope effects provide strong evidence for a stepwise mechanism, with a hydrogen atom abstraction in the rate-determining step.

  机理上已经研究了均相的分解钨酸盐W100O324催化的1,1-二苯乙烷和9-甲基-9 H-芴的光氧化。一级和二级动力学同位素效应为逐步机理提供了有力的证据，在速率确定步骤中具有氢原子的提取。
• Vinyl azide chemistry. Thermally induced reactions
  作者：Gerald Smolinsky、Coralie A. Pryde

  DOI：10.1021/jo01270a053

  日期：1968.6
• Characterization, via ESR Spectroscopy, of Radical Intermediates in the Photooxidation of Arylcarbinols by Ceric Ammonium Nitrate
  作者：Loris Grossi、Samantha Strazzari

  DOI：10.1021/jo991856t

  日期：2000.5.1

  The photooxidation by eerie ammonium nitrate (CAN) of several aryl and naphthylcarbinols has been studied by means of ESR spectroscopy. For all the investigated arylcarbinols, but not for the naphthyl derivatives, it has been possible to detect radical intermediates deriving from the parent alkoxyl radicals. In particular, in the photooxidation of 1,1-diphenylethanol, a bridged-radical intermediate has been detected. The assignment has been validated through experiments with two different labeled compounds: the 1,1-[2', 3', 4', 5', 6', 2", 3", 4", 5", 6"-H-2(10)]diphenylethanol and the 1,1-diphenyl[2, 2, 2-H-2(3)]ethanol. A similar bridged radical has been found to be formed in the photooxidation of triphenylmethanol, while, for the 1,1-diphenylpropanol, the only detectable species has been the ethyl radical deriving from a competitive beta-scission process. Finally, for the 2-phenylpropan-2-ol (cumyl alcohol), two radical species have been identified: the methyl, deriving from the beta-scission process, and the cyanomethylene, deriving from H-abstraction of the cumyloxyl radical from the solvent. A kinetic study on the competition of the two processes has also been conducted and the parameter a of the Arrhenius equation for the latter process have been estimated.
• Nickel-Catalyzed Direct Synthesis of Aryl Olefins from Ketones and Organoboron Reagents under Neutral Conditions
  作者：Chuanhu Lei、Yong Jie Yip、Jianrong Steve Zhou

  DOI：10.1021/jacs.7b02742

  日期：2017.5.3

  Nickel-catalyzed addition of arylboron reagents to ketones results in aryl olefins directly. The neutral condition allows acidic protons of alcohols, phenols, and malonates to be present, and fragile structures are also tolerated.

  镍催化的芳基硼试剂与酮的加成直接产生芳基烯烃。中性条件允许存在醇类、酚类和丙二酸酯的酸性质子，并且还可以容忍脆弱的结构。
• Kinetic deuterium isotope effects as evidence for a common ion-pair intermediate in solvolytic elimination and substitution reactions of 1,1-diphenylethyl chloride
  作者：Alf Thibblin、Harvinder Sidhu

  DOI：10.1021/ja00045a010

  日期：1992.9

  Solvolysis of 1,1-diphenyl-1-chloroethane (1-Cl) in acetonitrile at 25 o C provides the elimination product 1,1-diphenylethene (3). Addition of water or methanol to the acetonitrile increases the rate of elimination and gives rise to a second product, 1,1-diphenyl-1-hydroxyethane (1-OH) or 1,1-diphenyl-1-methoxyethane (1-OMe). The deuteriated analogue, 1,1-diphenyl-1-chloro[2,2,2- 2 H3]ethane (d-1-Cl)

  1,1-二苯基-1-氯乙烷 (1-Cl) 在 25 o C 下在乙腈中的溶剂分解提供消除产物 1,1-二苯基乙烯 (3)。向乙腈中加入水或甲醇可提高消除速率并产生第二个产物 1,1-二苯基-1-羟基乙烷 (1-OH) 或 1,1-二苯基-1-甲氧基乙烷 (1-OMe) . 氘代类似物 1,1-二苯基-1-氯[2,2,2-2 H3]乙烷 (d-1-Cl) 反应较慢