1,5-dicarbomethoxybicyclo<3.1.0>hexane | 3037-78-3

• 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: 1,5-dicarbomethoxybicyclo<3.1.0>hexane
• 英文别名: dimethyl bicyclo<3.1.0>hexane-1,5-dicarboxylate；Dimethyl bicyclo<3.1.0>hexan-1.5-dicarboxylat；Bicyclo<3.1.0>hexan-dicarbonsaeure-1,5-dimethylester；Dimethyl bicyclo[3.1.0]hexane-1,5-dicarboxylate
• CAS: 3037-78-3
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: FSXDBKXAZPSCIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1,5-dicarbomethoxybicyclo<3.1.0>hexane 在 氢氧化钾 、 碘苯二乙酸 、 碘 作用下， 以 甲醇 、 环己烷 为溶剂， 反应 2.0h， 生成 1,5-diiodobicyclo<3.1.0>hexane
  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：

  1,2-环戊烷二羧二甲酯 以54%的产率得到
  参考文献：
  名称：

  GARRATT P. J.; PORTER J. R., J. CHEM. RES. SYNOP.,(1987) N 4, 108-109

  摘要：

  DOI：

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：——
• Vinylcyclopropyl TMM diyls: access to eight-membered rings
  作者：Peter Jay Mikesell、R.Daniel Little

  DOI：10.1016/s0040-4039(01)00669-4

  日期：2001.6

  Vinylcyclopropyl substituted diazenes (e.g. 1 and 15) rearrange when healed. The chemistry takes place via the formation of a trimethylenemethane (TMM) diyl and provides access to eight-membered rings. When the cyclopropane is fused to a five-membered ring (e.g. 15) rearrangement leads to a structure resembling the taxotere framework. (C) 2001 Elsevier Science Ltd. All rights reserved.