2-phenylcyclohexanone dimethyl acetal | 143447-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenylcyclohexanone dimethyl acetal
• 英文别名: 1,1-dimethoxy-2-phenylcyclohexane；(2,2-dimethoxycyclohexyl)benzene；1,1-Dimethoxy-2-phenyl-cyclohexan
• CAS: 143447-66-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: YQNFAHQNTQMLLS-UHFFFAOYSA-N

物化性质

• 沸点：
  294.3±40.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenylcyclohexanone dimethyl acetal 在 三氟甲磺酸 、 水 作用下， 生成 2-苯基环己酮
  参考文献：
  名称：

  Novel electrophilic species equivalent to .alpha.-keto cations. Reactions of 0,0-diprotonated nitro olefins with benzenes yield arylmethyl ketones

  摘要：

  DOI：

  10.1021/jo00265a001
• 作为产物：
  描述：

  2-苯基环己酮 、 原甲酸三甲酯 在 Montmorillonite 作用下， 生成 2-phenylcyclohexanone dimethyl acetal
  参考文献：
  名称：

  构象受限的5-苯基戊-1-烯的分子内Meta光环加成。第一部分：双发色环己烷衍生物

  摘要：

  1-烯丙基-2-苯基环己烷和1-苄基-2-乙烯基环己烷的顺式异构体主要产生1：3加成，而反式异构体显示出2：6加成的高选择性，这可以通过空间相互作用来解释。在环己烷环的链烯基取代的碳上引入第三取代基OH或OCH 3几乎仅以1：3加成。可以用导致2：6加成的构象中更大的位阻来解释这一点。

  DOI：

  10.1016/0040-4020(95)00373-g

文献信息

• A generalized approach for iron catalyzed chemo- and regioselective formation of anti-Markovnikov acetals from styrene derivatives
  作者：Abhishek Dutta Chowdhury、Goutam Kumar Lahiri

  DOI：10.1039/c2cc17889c

  日期：——

  in the presence of pyridine-2,6-dicarboxylic acid and PhI(OAc)(2) can efficiently catalyze the formation of chemoselective dialkyl acetals from styrene derivatives with anti-Markovnikov regioselectivity in good to high yields under mild and benign reaction conditions.

  在吡啶2,6-二羧酸和PhI（OAc）（2）存在下的Fe（BF（4））（2）.6H（2）O可以有效地催化苯乙烯衍生物与抗氧化剂形成化学选择性二烷基乙缩醛-Markovnikov区域选择性在温和和良性反应条件下具有良好至高收率。
• Novel self-coupling reaction of cyclic ketones under a high-pressure mercury lamp
  作者：Shun-Jun Ji、Masatoshi Matsushita、T.Tomoyoshi Takahashi、C.Akira Horiuchi

  DOI：10.1016/s0040-4039(99)01357-x

  日期：1999.9

  A novel self-coupling reaction in alcohol or hexane-water of cycloalkanone (cycloheptanone, cyclooctanone, and cyclododecanone) with irradiation under a high-pressure mercury lamp yielded the corresponding pinacol-type compound in good yields. In the case of cyclohexanone, 2-methyl-, 2-phenyl-, 4-methylcyclohexanone, 5 alpha- and 5 beta-cholestan-3-one, the pinacol derivatives were not obtained and the dimethyl acetals were given. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Electrostatic modulation of hydroxyl group ionization in acidic media. Evidence for the competitive operation of intramolecular SN2 reactions
  作者：Joanna T. Negri、Leo A. Paquette

  DOI：10.1021/ja00049a014

  日期：1992.11

  The acid-catalyzed cyclodehydration of the cis and trans isomers of 2-substituted 1-(3-hydroxypropyl)cyclohexanols results in the formation of spirocyclic tetrahydrofurans. The stereochemical course of these reactions is highly varied, ranging from a dominant preference for retention when R = OCH3 to modestly favored inversion when R = CH3. Experiments with O-18-labeled diols show that in the methoxyl series most of the isotope is retained irrespective of relative stereochemistry. On the other hand, the pair of phenyl-substituted isomers responds by losing approximately 50% of the label. The isotopic level in the product erodes further when R = CH3. The stereochemical and isotopic labeling results are interpreted in terms of competing intramolecular S(N)2 and classical S(N)1 pathways. The extent to which cooperative nucleophilic attack with loss of the primary hydroxyl is facilitated reaches a maximum in the methoxyl-substituted diols, as a consequence of electrostatic inhibition of tertiary carbocation formation. As this effect is progressively lessened, the percentage of S(N)1 response rises. At no time, however, do the stereoisomeric carbocations interconvert conformationally prior to cyclization.
• Reactions of O,O-diprotonated nitro olefins with benzenes. Formations of phenylacetones, 4H-1,2-benzoxazines and biarylacetone oximes
  作者：Tomohiko Ohwada、Kazuaki Okabe、Toshiharu Ohta、Koichi Shudo

  DOI：10.1016/s0040-4020(01)89066-9

  日期：1990.1