methyl cyclohepta-1,6-diene-1-carboxylate | 42403-33-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl cyclohepta-1,6-diene-1-carboxylate
• 英文别名: 2-(methoxycarbonyl)cyclohepta-1,3-diene；Cycloheptadiencarbonsaeure-methylester；2-Methoxycarbonyl-1.3-cycloheptadien；2-Carbomethoxy-1.3-cycloheptadien
• CAS: 42403-33-8
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: KGEJMNQZHPFAOB-UHFFFAOYSA-N

物化性质

• 沸点：
  30-35 °C(Press: 0.35 Torr)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl cyclohepta-1,6-diene-1-carboxylate 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 1,7-epoxybicyclo<5.1.0>cyclohept-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis of disodium 3-[(1-carboxylatoethenyl)oxy]cyclohepta-1,6-diene-1-carboxylate: a seven-membered ring analog of chorismate

  摘要：

  DOI：

  10.1021/jo00252a033
• 作为产物：
  描述：

  1-hydroxy-cycloheptanecarbonitrile 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 硫酸 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 sodium iodide 作用下， 以 四氯化碳 、 丙酮 、 苯 为溶剂， 反应 89.5h， 生成 methyl cyclohepta-1,6-diene-1-carboxylate
  参考文献：
  名称：

  Synthesis of disodium 3-[(1-carboxylatoethenyl)oxy]cyclohepta-1,6-diene-1-carboxylate: a seven-membered ring analog of chorismate

  摘要：

  DOI：

  10.1021/jo00252a033

文献信息

• Preparation and reactions of methoxycarbonyl-substituted cycloheptadienyliron tricarbonyl cations: unusual regiochemistry during the addition of stabilized enolate nucleophiles
  作者：Anthony J. Pearson、Marco P. Burello

  DOI：10.1039/c39890001332

  日期：——

  Tricarbonyl(1-methoxycarbonylcycloheptadienyl)iron hexafluorophosphate (9) and tricarbonyl(3-methoxycarbonylcycloheptadienyl)iron hexafluorophosphate (12) were prepared and thier reactions with a range of nucleophiles were examined. Cyanide, borohydride, and malonate enolate all added exclusively to C-2 of (9) and predominantly to C-2 of (12), while Me2CuLi, hydroxide, and potassium phthalimide all

  制备了三羰基（1-甲氧基羰基环庚二烯基）六氟磷酸铁（9）和三羰基（3-甲氧基羰基环庚二烯基）六氟磷酸铁（12），并研究了与一系列亲核试剂的反应。氰化物，硼氢化物和丙二酸烯醇盐都专门添加到（9）的C-2中，主要添加到（12）的C-2中，而Me 2 CuLi，氢氧化物和邻苯二甲酰亚胺钾都在两种配合物的C-1处反应。在添加NaCH（CO 2 Me）2的过程中，区域选择性异常，反映了酯取代基对二烯基-铁系统的显着扰动。
• Preparation and reactions of tricarbonyliron complexes of methyl cycloheptadienecarboxylates and methylcycloheptadienes
  作者：Anthony J. Pearson、Marco P. Burello

  DOI：10.1021/om00037a072

  日期：1992.1

  The preparation and reactions with nucleophiles of tricarbonyl[1-(methoxycarbonyl)cycloheptadienylium]iron hexafluorophosphate (7) and tricarbonyl[3-(methoxycarbonyl)cycloheptadienylium]iron hexafluorophosphate (12) were studied. Unusual regioselectivity was observed for the addition of dimethyl malonate enolate to these complexes, viz., exclusively C(2) addition to 7 and predominantly C(2) addition to 12, giving enediyl complexes. Replacement of CO ligand with triphenylphosphine does not affect this regioselectivity. Attempts to rationalize these observations using C-13 NMR spectroscopy and extended Huckel calculations met with limited success. The preparation and reactions of tricarbonyl(1-methylcycloheptadienylium)iron hexafluorophosphate (31) are described. Addition of malonate to 31 proceeds with exclusive formation of the substituted cycloheptadiene complex, thus confirming the marked effect of the ester substituent on the reactivity of complexes 7 and 12.
• Pikulik,I.; Childs,R.F., Canadian Journal of Chemistry, 1977, vol. 55, p. 251 - 258
  作者：Pikulik,I.、Childs,R.F.

  DOI：——

  日期：——
• Silver(I) ion-catalyzed rearrangements of strained .sigma. bonds. XXII. Kinetic deuterium isotope and electronic effects in the silver(I) promoted type .gamma. isomerization of 1-alkyltricyclo[4.1.0.0.2,7]heptanes. Mechanistic analysis of the formation of bicyclo[3.2.0]hept-6-enes
  作者：Leo A. Paquette、Gerald Zon

  DOI：10.1021/ja00808a036

  日期：1974.1
• PEARSON, ANTHONY J.;BURELLO, MARCO P., J. CHEM. SOC. CHEM. COMMUN.,(1989) N8, C. 1332-1333
  作者：PEARSON, ANTHONY J.、BURELLO, MARCO P.

  DOI：——

  日期：——