1-(methoxycarbonyl)-3-methylene-1-cyclobutanol | 83249-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(methoxycarbonyl)-3-methylene-1-cyclobutanol
• 英文别名: 1-carbomethoxy-3-methylenecyclobutanol；Methyl 1-hydroxy-3-methylidenecyclobutane-1-carboxylate
• CAS: 83249-15-4
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: PTIFEIBLJSONOJ-UHFFFAOYSA-N

物化性质

• 熔点：
  38.5-39.5 °C
• 沸点：
  183.0±30.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 3-phenyl-2,2-dichlorobicyclo<1.1.1>pentanecarboxylate 在 ruthenium(IV) oxide 、 sodium hydroxide 、 sodium hypochlorite 、 偶氮二异丁腈 、 溴 、 三正丁基氢锡 、 silver nitrate 、 mercury(II) oxide 作用下， 以 四氯化碳 、 乙醚 、 水 、 1,2-二溴乙烷 为溶剂， 反应 132.0h， 生成 1-(methoxycarbonyl)-3-methylene-1-cyclobutanol
  参考文献：
  名称：

  Polar substituent effects in 1,3-disubstituted bicyclo[1.1.1]pentanes

  摘要：

  DOI：

  10.1021/jo00146a031

文献信息

• Inductive charge dispersal in the solvolysis of 3-substituted bicyclo[1.1.1] pentyl bromides
  作者：Cyril A. Grob、Cheng Xi Yang、Ernest W. Della、Dennis K. Taylor

  DOI：10.1016/s0040-4039(00)79433-0

  日期：1991.10

  Solvolysis rates and products of 3-substituted bicyclo[1.1.1]pentyl bromides indicate extremely strong inductive charge dispersal in the ionization to bicyclo[1.1.1]pentyl-1-cations, the precursors of 3-methylenecyclobutanols.

  3-取代的双环[1.1.1]戊基溴化物的溶剂分解速率和产物表明，在离子化为双环[1.1.1]戊基-1-阳离子（3-亚甲基环丁醇的前体）的过程中，极强的感应电荷分散。
• Bridgehead Carbocations: A Solvolytic Study of 1-Bromobicyclo[1.1.1]pentane and Its Bridgehead-Substituted Derivatives
  作者：Ernest W. Della、Cyril A. Grob、Dennis K. Taylor

  DOI：10.1021/ja00093a014

  日期：1994.7

  The rate constants (k) for solvolysis of a range of 3-X-substituted bicyclo[1.1.1]pentyl bromides in 80% aqueous ethanol have been measured and a linear relationship found to exist between log k and the inductive/field constant sigma(I). These observations, together with the results of isotope and solvent effect studies described below, have been interpreted as evidence for the formation of 1-bicyclo[1.1.1]pentyl cations in the ionization step in preference to mechanisms in which either ring-opening is concerted with ionization to give 3-methylenecyclobutyl cations or ionization is accompanied by ring-contraction to give bicyclo[1.1.0]butyl-1-carbinyl cations. The latter mechanisms would have been expected to show the effects of strong pi-donor substituent participation, a phenomenon which was not observed. A comparison of the rates of solvolysis of the parent bromide and its 3-deuterated analog is characterized by a large deuterium-isotope effect (k(H)/k(D) = 1.30) which, combined with the observation that 1-bromobicyclo[1.1.1]pentane solvolyses with enhanced rates in solvents which are strong hydrogen bonding accepters, lends support to the view that the 1-bicyclo[1.1.1]pentyl cation derives substantial stabilization from sigma-hyperconjugative interactions.
• APPLEQUIST, D. E.;RENKEN, T. L.;WHEELER, J. W., J. ORG. CHEM., 1982, 47, N 25, 4985-4995
  作者：APPLEQUIST, D. E.、RENKEN, T. L.、WHEELER, J. W.

  DOI：——

  日期：——