syn-Dimethyl tetracyclo<5.5.0.03,5.09,11>dodec-1(7)-ene-4,10-dicarboxylate | 160497-61-0

• 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: syn-Dimethyl tetracyclo<5.5.0.03,5.09,11>dodec-1(7)-ene-4,10-dicarboxylate
• 英文别名: syn-Dimethyl tetracyclo<5.5.0.0^3,5.0^9,11>dodec-1(7)-ene-4,10-dicarboxylate
• CAS: 160497-61-0
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: TYBBQALKTFORPG-KXSLGULGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  syn-Dimethyl tetracyclo<5.5.0.03,5.09,11>dodec-1(7)-ene-4,10-dicarboxylate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以98%的产率得到
  参考文献：
  名称：

  Synthesis of a New System Containing a Pyramidalized Double Bond: cis-Dicarbomethoxydihydroheptalene and Its Reaction with Benzyne

  摘要：

  The strained system syn-1 was the object of synthetic and structural studies because of its double bond pyramidalization. The starting material, cis-3, 8-dicarbomethoxy-3,8-dihydroheptalene, was synthesized by two different approaches. Addition of ethyl diazoacetate then gave syn-addition product 2. Transesterification and NBS-bromination followed by Zn-AcOH elimination resulted in the formation of cis-dihydroheptalene 5, which was also synthesized by silica gel catalyzed isomerization of the trans-5 isomer. Addition of benzyne to cis-5 gave the target compound syn-1, whose structure was investigated by X-ray diffraction. These data show its pyramidalization angle to be 16.8 degrees.

  DOI：

  10.1021/jo00109a012
• 作为产物：
  描述：

  甲醇 、 syn-Diethyl tetracyclo<5.5.0.0^3,5.0^9,11>dodec-1(7)-ene-4,10-dicarboxylate 在 对甲苯磺酸 作用下， 反应 72.0h， 以95%的产率得到syn-Dimethyl tetracyclo<5.5.0.03,5.09,11>dodec-1(7)-ene-4,10-dicarboxylate
  参考文献：
  名称：

  Synthesis of a New System Containing a Pyramidalized Double Bond: cis-Dicarbomethoxydihydroheptalene and Its Reaction with Benzyne

  摘要：

  The strained system syn-1 was the object of synthetic and structural studies because of its double bond pyramidalization. The starting material, cis-3, 8-dicarbomethoxy-3,8-dihydroheptalene, was synthesized by two different approaches. Addition of ethyl diazoacetate then gave syn-addition product 2. Transesterification and NBS-bromination followed by Zn-AcOH elimination resulted in the formation of cis-dihydroheptalene 5, which was also synthesized by silica gel catalyzed isomerization of the trans-5 isomer. Addition of benzyne to cis-5 gave the target compound syn-1, whose structure was investigated by X-ray diffraction. These data show its pyramidalization angle to be 16.8 degrees.

  DOI：

  10.1021/jo00109a012

文献信息

• Bromination of Decalin and Its Derivatives. 9. High Temperature Bromination
  作者：Arif Dastan、M. Nawaz Tahir、Dinçer Ülkü、Philip B. Shevlin、Metin Balci

  DOI：10.1021/jo9700843

  日期：1997.6.13

  Thermal and photobromination of decalin, 1, was studied, trans,cis,trans-2,5,7,9-tetrabromooctalin 2, was obtained as the major product along with smaller amounts of bromonaphthalene derivatives. The structures of the products were determined by H-1- and C-13-NMR data and single X-ray structural analysis. Bromination of the two decalin derivatives 9 and 10 results in the formation of single isomers 11 and 12, respectively. The three tetrabromides 2, 11, and 12 were shown by molecular mechanics calculations to be the most stable stereoisomer in each case. The formation of these tetrabromides under thermodynamic control is postulated.