1,6-dicarbomethoxybicyclo<4.1.0>heptane | 103478-30-4

• 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: 1,6-dicarbomethoxybicyclo<4.1.0>heptane
• 英文别名: dimethyl bicyclo<4.1.0>heptane-1,6-dicarboxylate；bicyclo(4.1.0)heptane-1,6-dicarboxylic acid dimethyl ester；Dimethyl bicyclo[4.1.0]heptane-1,6-dicarboxylate
• CAS: 103478-30-4
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: HCTGXWMMAAGTSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-dicarbomethoxybicyclo<4.1.0>heptane 在 氢氧化钾 、 溴 、 magnesium sulfate 、 mercury(II) oxide 作用下， 以 甲醇 为溶剂， 反应 3.83h， 生成 6-叔丁基双环[4.1.0]庚烷-1-羧酸
  参考文献：
  名称：

  1,2-Bridged cyclopropenes

  摘要：

  The dehalogenations of 1,5-dihalobicyclo[3.1.0]hexanes and 1,6-dihalobicyclo[4.1.0]heptanes have been studied in solution and in the gas phase. The solution reactions led to the formation of bicyclo[3.1.0]hex-1(5)-ene and bicyclo[4.1.0]hept-1(6)-ene, respectively, but this was followed by rapid ene reactions forming dimers, which then coupled to form tetramers. The cyclopropenes could be trapped as Diels-Alder adducts. In the gas phase, with use of either potassium atoms or solid methyllithium, the products of thermal ring opening, methylenecyclopentene and methylenecyclohexene, were formed. A set of theoretical calculations was carried out dealing with the strain energies, inversion barriers, bond properties, and atom properties of bicyclo[1.1.0]but-1(3)-ene, bicyclo[2.1.0]pent-1(4)-ene, and the cyclopropenes from the experimental study. Whereas bicyclohexene and bicycloheptene appear to be fairly normal compounds except for their high strain energies, bicyclopentene may be a transition state for the carbon scrambling of methylenecyclobutylidene, and bicyclobutene has an unusual structure and charge-density distribution.

  DOI：

  10.1021/ja00021a024
• 作为产物：
  描述：

  1-(氯甲基)环己烷-1,2-二甲酸二甲酯 在 sodium methylate 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 1,6-dicarbomethoxybicyclo<4.1.0>heptane
  参考文献：
  名称：

  1,2-Bridged cyclopropenes

  摘要：

  The dehalogenations of 1,5-dihalobicyclo[3.1.0]hexanes and 1,6-dihalobicyclo[4.1.0]heptanes have been studied in solution and in the gas phase. The solution reactions led to the formation of bicyclo[3.1.0]hex-1(5)-ene and bicyclo[4.1.0]hept-1(6)-ene, respectively, but this was followed by rapid ene reactions forming dimers, which then coupled to form tetramers. The cyclopropenes could be trapped as Diels-Alder adducts. In the gas phase, with use of either potassium atoms or solid methyllithium, the products of thermal ring opening, methylenecyclopentene and methylenecyclohexene, were formed. A set of theoretical calculations was carried out dealing with the strain energies, inversion barriers, bond properties, and atom properties of bicyclo[1.1.0]but-1(3)-ene, bicyclo[2.1.0]pent-1(4)-ene, and the cyclopropenes from the experimental study. Whereas bicyclohexene and bicycloheptene appear to be fairly normal compounds except for their high strain energies, bicyclopentene may be a transition state for the carbon scrambling of methylenecyclobutylidene, and bicyclobutene has an unusual structure and charge-density distribution.

  DOI：

  10.1021/ja00021a024

文献信息

• Synthesis of meso bridgehead dienes [3.3] sigmatropic rearrangements of 1,n-divinyl bicyclo [n,m,o] alkanes
  作者：K.J. Shea、A.C. Greeley、S. Nguyen、P.D. Beauchmap、S. Wise

  DOI：10.1016/s0040-4039(00)88291-x

  日期：——

  [3.3]Sigmatropic rearrangement of 1,n-divinyl bicyclo[n,m,o]alkanes results in formation of meso bridgehead dienes that contain a ,-1,5-cycloalkadiene linkage

  [3.3] 1，n-二乙烯基双环[n，m，o]烷烃的向亲性重排导致形成包含，-1,5-环链二烯键的内消旋桥头二烯
• SHEA K. J.; GREELEY A. C.; NGUYEN S.; BEAUCHAMP P. D.; AUE D. H.; WITZEMA+, J. AMER. CHEM. SOC., 108,(1986) N 19, 5901-5908
  作者：SHEA K. J.、 GREELEY A. C.、 NGUYEN S.、 BEAUCHAMP P. D.、 AUE D. H.、 WITZEMA+

  DOI：——

  日期：——
• GARRATT P. J.; PORTER J. R., J. CHEM. RES. SYNOP.,(1987) N 4, 108-109
  作者：GARRATT P. J.、 PORTER J. R.

  DOI：——

  日期：——