4-(methoxycarbonyl)cyclohepta-2,4,6-trien-1-one | 108462-35-7

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 4-(methoxycarbonyl)cyclohepta-2,4,6-trien-1-one
• 英文别名: 4-methoxycarbonylcycloheptatrienone；5-oxo-cyclohepta-1,3,6-trienecarboxylic acid methyl ester；5-Oxo-cyclohepta-1,3,6-triencarbonsaeure-methylester；Methyl 5-oxocyclohepta-1,3,6-triene-1-carboxylate
• CAS: 108462-35-7
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: CMSFDKPNORLRFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 4-methoxy-4-<(trimethylsilyl)oxy>cyclohepta-1,5-diene-1-carboxylate 在 2,2-dichloroethanol,oxovanadium(2+) 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以54%的产率得到4-(methoxycarbonyl)cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Versatile synthesis of tropones by reaction of rhodium(II)-stabilized vinylcarbenoids with 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene

  摘要：

  Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene leads to [3 + 4] annulation products by a tandem cyclopropanation/Cope rearrangement sequence. The resulting cycloheptadienes are readily converted to cycloheptatrienones either by hydrolysis with mild acid followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or by treatment with dichloroethoxyoxovanadium. The efficiency of the general strategy was demonstrated through a short synthesis of nezukone.

  DOI：

  10.1021/jo00022a041

文献信息

• Diels-alder cycloaddition reactions of cyclopropenone ketals
  作者：Dale L. Boger、Christine E. Brotherton

  DOI：10.1016/s0040-4020(01)90567-8

  日期：1986.1

  Diels-Alder cycloadditions of the cyclopropenone ketal 1 with representative electron-deficient, electron-rich and neutral dienes are presented. The results observed are consistent with the potential for the strained olefin of the cyclopropenone ketal to exhibit accelerated participation in both inverse electron demand (LUMOdienecontrolled) and normal(HOMOdienecontrolled) Diels-Alder reactions. Approaches

  提出了具有代表性的缺电子，富电子和中性二烯的环丙烯酮缩酮1的Diels-Alder环加成反应。观察到的结果与环丙烯酮缩酮的应变烯烃在反电子需求（LUMO二烯控制）和正电子（HOMO二烯控制）Diels-Alder反应中显示出加速参与的潜力相一致。提出了基于环丙酮缩酮1的室温和压力促进的Diels-Alder反应引入环庚酮，对苯二酚的方法。
• Terrestrial heat flow in Junggar Basin, Northwest China
  作者：Shejiao Wang、Shengbiao Hu、Tiejun Li、Jiyang Wang、Wenzhi Zhao

  DOI：10.1007/bf02886273

  日期：2000.10

  Based on temperature logs of 117 boreholes and thermal conductivity of 119 rock samples, the first group of 35 heat flow data in the Junggar Basin are presented. The thermal gradients vary between 11.6 and 26.5 degreesC/km, and the thermal conductivity changes from 0.17 to 3.6 W/mK. Heat flow ranges from 23.4 to 53.7 mW/m(2) with a mean of (42.3+/-7.7) mW/m2. The heat flow pattern shows that heat flow is higher in the uplifts and lower in the depressions. The factors affecting the heat flow and its distribution include basin type, basement structure, sediment thickness, radioactive heat generation, etc. The overall low present-day heat flow in the Junggar Basin reflected its tectonothermal evolution characterized by lithospheric thickening, thrust and fault at shallow crust as well as consequently quick subsidence during the Late Cenozoic.