4,4-<(1R,2R)-1,2-(diphenyl)ethylenedioxi>-2,5-cyclohexadienone | 169267-16-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,4-<(1R,2R)-1,2-(diphenyl)ethylenedioxi>-2,5-cyclohexadienone
• 英文别名: (+)-(1R,2R)-1,2-Diphenylethylene monoketal of p-benzoquinone；(2R,3R)-2,3-diphenyl-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
• CAS: 169267-16-7
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: VZKIYGGLHUVOMC-RTBURBONSA-N

物化性质

• 沸点：
  477.5±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-<(1R,2R)-1,2-(diphenyl)ethylenedioxi>-2,5-cyclohexadienone 在 吡啶 、 indium 、 氢氧化钾 、 氯化亚砜 、 montmorillonite K-10 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 203.08h， 生成 联苯乙醛
  参考文献：
  名称：

  From p-benzoquinone to cyclohexane chirons: first asymmetric synthesis of (+)-rengyolone and (+)- and (−)-menisdaurilide

  摘要：

  Starting from a common, easily available, enantiopure monoketal of p-benzoquinone, the synthesis of a large number of cyclohexane chirons has been achieved. The first synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide has been performed from one of these new building blocks. The wide variety of functional groups of this series of chirons makes them useful for subsequent synthetic processes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00357-4
• 作为产物：
  描述：

  4,4-bis-<(1R,2R)-1,2-(diphenyl)ethylenedioxy>-2,5-cyclohexadiene 在 盐酸 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 1.0h， 以85%的产率得到4,4-<(1R,2R)-1,2-(diphenyl)ethylenedioxi>-2,5-cyclohexadienone
  参考文献：
  名称：

  First Preparation of Optically Pure Ketals of p-Benzoquinone

  摘要：

  DOI：

  10.1021/jo00117a048

文献信息

• Diels–Alder Reactions of Masked p-Benzoquinones
  作者：Pedro de March、Marta Figueredo、Josep Font、Sonia Rodrı́guez

  DOI：10.1016/s0040-4020(00)00276-3

  日期：2000.5

  Phenylthiomonoketal 3 works effectively as masked p-benzoquinone in Diels–Alder reactions. These cycloadditions may be performed with certain Lewis acid catalysts and give rise exclusively to endo adducts with a good to excellent anti-facial selectivity.

  Phenylthiomonoketal 3作品有效地掩盖p中的Diels-Alder反应对苯醌。这些环加成可以用某些路易斯酸催化剂进行，并且仅以良好或优异的抗表面选择性产生内加合物。
• Toward the Synthesis of (‒)-Codeine by Chiral Auxiliary-Mediated Nitrone Cycloaddition
  作者：Peter Metz、Julia Rautschek

  DOI：10.3987/com-16-s(s)82

  日期：——

  Application of a C-2-symmetric dioxolane moiety as chiral auxiliary for an asymmetric intramolecular nitrone cycloaddition was studied as a possible key step for the enantioselective synthesis of (-)-codeine. A cycloaddition precursor bearing a 1,2-diphenylethylene acetal was selected that was readily accessible in ten steps from isovanillin. It underwent nitrone cycloaddition and after a consecutive transformation, an isoxazolidine intermediate with the absolute and relative configuration required for (-)-codeine was obtained.
• New, highly efficient syntheses of rac-, (R)- and (S)-4-hydroxy-2-cyclohexenone
  作者：Pedro de March、Maria Escoda、Marta Figueredo、Josep Font、Elena Garcı́a-Garcı́a、Sonia Rodrı́guez

  DOI：10.1016/s0957-4166(00)00451-1

  日期：2000.11

  Both enantiomers of 4-hydroxy-2-cyclohexenone have been synthesised from chiral p-benzoquinone equivalents through very short and simple sequences in good overall yields. (C) 2000 Published by Elsevier Science Ltd.
• De March; Escoda; Figueredo, Anales de Quimica, 1997, vol. 93, # 2, p. 81 - 87
  作者：De March、Escoda、Figueredo、Font、Mcdrano

  DOI：——

  日期：——
• From p-benzoquinone to useful chiral cyclohexane building blocks
  作者：Félix Busqué、Pedro de March、Marta Figueredo、Josep Font、Sonia Rodrı́guez

  DOI：10.1016/s0957-4166(01)00557-2

  日期：2001.12

  A straightforward and efficient access to 12 new cyclohexane chirons from an easily available enantiopure monoketal of p-benzoquinone is described. These chirons possess a variety of functional groups which render them useful for further synthetic elaboration. (C) 2002 Elsevier Science Ltd. All rights reserved.