2-allyl-4,4,5-trimethoxycyclohexa-2,5-dienone | 89067-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-allyl-4,4,5-trimethoxycyclohexa-2,5-dienone
• 英文别名: 2,5-Cyclohexadien-1-one, 4,4,5-trimethoxy-2-(2-propenyl)-；4,4,5-trimethoxy-2-prop-2-enylcyclohexa-2,5-dien-1-one
• CAS: 89067-49-2
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: DWMBJTGPUZIAHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-allyl-4,4,5-trimethoxycyclohexa-2,5-dienone 在 四丁基氟化铵 、 四氯化钛 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 (+/-)-(2α,4α,5β,5aα)-4-(4-hydroxy-3-methoxyphenyl)-2,5a-methano-7-methoxy-5-methyl-8H-2,3,4,5-tetrahydro-1-benzoxepin-8-one
  参考文献：
  名称：

  Synthesis of neolignans via a proposed biosynthetic intermediate. Total synthesis of (.+-.)-futoenone

  摘要：

  The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. The results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo[3.2.1]octenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (+/-)-futoenone via a benzylic cation intermediate related to quinone methide 3 is reported. The results provide support for Gottlieb's proposal that several different neolignans arise from a common biosynthetic precursor. The efficient synthesis of (+/-)-futoenone and related spiro[5.5]undecanoids using a Buchi quinone ketal cycloaddition is also described.

  DOI：

  10.1021/jo00072a017
• 作为产物：
  描述：

  4,5-二甲氧基-2-(2-丙烯基)苯酚 在 lithium perchlorate 作用下， 以 甲醇 为溶剂， 以87%的产率得到2-allyl-4,4,5-trimethoxycyclohexa-2,5-dienone
  参考文献：
  名称：

  Shizuri, Yoshikazu; Yamamura, Shosuke, Tetrahedron Letters, 1983, vol. 24, # 45, p. 5011 - 5012

  摘要：

  DOI：

文献信息

• Cationic [5+2] cycloaddition reactions promoted by trimethylsilyl triflate in highly polar media
  作者：Jon L. Collins、Paul A. Grieco、John K. Walker

  DOI：10.1016/s0040-4039(97)00030-0

  日期：1997.2

  Trimethylsilyl triflate is an effective reagent in 3.0 M lithium perchlorate-ethyl acetate for promoting cationic [5+2] cycloaddition reactions.

  三氟甲磺酸三甲基甲硅烷基酯是3.0 M高氯酸锂-乙酸乙酯中用于促进阳离子[5 + 2]环加成反应的有效试剂。
• Development of an Automated Microfluidic Reaction Platform for Multidimensional Screening: Reaction Discovery Employing Bicyclo[3.2.1]octanoid Scaffolds
  作者：John R. Goodell、Jonathan P. McMullen、Nikolay Zaborenko、Jason R. Maloney、Chuan-Xing Ho、Klavs F. Jensen、John A. Porco、Aaron B. Beeler

  DOI：10.1021/jo901073v

  日期：2009.8.21

  All automated, silicon-based microreactor system has been developed for rapid, low-volume, multidimensional reaction screening. Use of the microfluidic platform to identify transformations of densely functionalized bicyclo[3.2.1]octanoid scaffolds will be described.
• Shizuri, Yoshikazu; Yamamura, Shosuke, Tetrahedron Letters, 1983, vol. 24, # 45, p. 5011 - 5012
  作者：Shizuri, Yoshikazu、Yamamura, Shosuke

  DOI：——

  日期：——
• Synthesis of neolignans via a proposed biosynthetic intermediate. Total synthesis of (.+-.)-futoenone
  作者：Steven R. Angle、Kenneth D. Turnbull

  DOI：10.1021/jo00072a017

  日期：1993.9

  The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. The results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo[3.2.1]octenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (+/-)-futoenone via a benzylic cation intermediate related to quinone methide 3 is reported. The results provide support for Gottlieb's proposal that several different neolignans arise from a common biosynthetic precursor. The efficient synthesis of (+/-)-futoenone and related spiro[5.5]undecanoids using a Buchi quinone ketal cycloaddition is also described.