(+)-(1R,2R)-1,2-Dimethylethylene monoketal of p-benzoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(1R,2R)-1,2-Dimethylethylene monoketal of p-benzoquinone
• 英文别名: (2R,3R)-2,3-dimethyl-1,4-dioxaspiro[4.5]deca-6,9-dien-8-one
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: PKEIDHDAQJKTAS-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,3,4,5-四氢吡啶1-氧化物 、 (+)-(1R,2R)-1,2-Dimethylethylene monoketal of p-benzoquinone 以 氯仿 、 甲苯 为溶剂， 反应 0.17h， 以83%的产率得到(4aRS,10aSR,10bSR)-4,4-[(trans-1,2-dimethylethylene)dioxy]-4,4a,7,8,9,10,10a,10b-octahydro-1H-pyrido[1,2-b][1,2]benzisoxazol-1-one
  参考文献：
  名称：

  Asymmetric Induction in the Cycloaddition of a Masked p-Benzoquinone to Cyclic Nitrones

  摘要：

  1,3-Dipolar cycloadditions of cyclic nitrones to achiral and chiral p-benzoquinone monoketals have shown poor chemo-and stereoselectivity. To overcome these problems, a highly efficient strategy has been set up on the basis of the temporary conjugate addition of thiophenol to the dipolarophile. The phenylthio derivative 10b, available in both enantiopure forms, has demonstrated to be effective as a masked chiral synthetic equivalent of p-benzoquinone in the model reaction.

  DOI：

  10.1021/jo971035t
• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 、 2,3-丁二醇 在 三氟化硼乙醚 作用下， 以 乙二醇二甲醚 为溶剂， 以68%的产率得到(+)-(1R,2R)-1,2-Dimethylethylene monoketal of p-benzoquinone
  参考文献：
  名称：

  Synthesis of quinone monoketals by diol exchange

  摘要：

  A new procedure for the synthesis of quinone monoketals derived from a variety of diols has been developed involving treatment of the readily available dimethyl ketals with diols and BF3.etherate in DME.

  DOI：

  10.1016/s0040-4039(00)60993-0

文献信息

• 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：——
• First Preparation of Optically Pure Ketals of p-Benzoquinone
  作者：Pedro de March、Maria Escoda、Marta Figueredo、Josep Font、Angel Alvarez-Larena、Juan F. Piniella

  DOI：10.1021/jo00117a048

  日期：1995.6
• Synthesis of quinone monoketals by diol exchange
  作者：Michael C. Pirrung、David S. Nunn

  DOI：10.1016/s0040-4039(00)60993-0

  日期：1992.10

  A new procedure for the synthesis of quinone monoketals derived from a variety of diols has been developed involving treatment of the readily available dimethyl ketals with diols and BF3.etherate in DME.
• Asymmetric Induction in the Cycloaddition of a Masked <i>p</i>-Benzoquinone to Cyclic Nitrones
  作者：Pedro de March、Maria Escoda、Marta Figueredo、Josep Font、Angel Alvarez-Larena、Juan F. Piniella

  DOI：10.1021/jo971035t

  日期：1997.10.1

  1,3-Dipolar cycloadditions of cyclic nitrones to achiral and chiral p-benzoquinone monoketals have shown poor chemo-and stereoselectivity. To overcome these problems, a highly efficient strategy has been set up on the basis of the temporary conjugate addition of thiophenol to the dipolarophile. The phenylthio derivative 10b, available in both enantiopure forms, has demonstrated to be effective as a masked chiral synthetic equivalent of p-benzoquinone in the model reaction.