2,5-dimethyl-(1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.1^2,5]dodec-3-en-11-one | 1191092-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2,5-dimethyl-(1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.1^2,5]dodec-3-en-11-one
• 英文别名: (1R,2R,5S,6S)-2,5-dimethyl-12-oxatricyclo[4.4.1.12,5]dodec-3-en-11-one
• CAS: 1191092-66-6
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: NKVVKLFUVVYMEY-QZHINBJYSA-N

物化性质

• 沸点：
  294.6±40.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  2,5-dimethyl-(1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.1^2,5]dodec-3-en-11-one 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到(1R,2S,3S,6R,7R,8S)-2,7-dimethyl-4,5,14,15-tetraoxatetracyclo[6.4.1.12,7.13,6]pentadecan-13-one
  参考文献：
  名称：

  具有改善植物生长调节活性的新型臭氧的合成与生物学评价

  摘要：

  诱导从2,7-二溴环庚酮生成的氧氧基烯丙基碳正离子与各种呋喃进行[4 + 3]环加成反应，得到一系列的12-氧三环-[4.4.1.1 2,5 ] -dodec-3-en-11 -一个加合物。使用类似的方法，使用薄荷醇和两个同源的脂族二溴酮制备另外两个环加合物。臭氧与加合物的偶极环加成以可变的收率提供了相应的仲臭氧化物（即1,2,4-三氧戊环）。通过在B3LYP / 6-31 + G *水平上的量子力学研究了臭氧，研究了包括紧密接触的结构特征，这些紧密接触可能有助于增强臭氧的稳定性。这些臭氧化物及其相应的前体环加合物对双色高粱根系生长的影响和黄瓜在5.0×10评价-4摩尔大号-1。还评估了最活跃的环加合物和臭氧化物对杂草物种大叶番薯（Ipomoea grandifolia）和臂状臂锈菌（Brachiaria decumbens）的影响，并对结果进行了讨论。与先前在我们实验室中合成的臭氧化物相

  DOI：

  10.1021/jf902540z
• 作为产物：
  描述：

  2,5-二甲基呋喃 、 2,7-dibromocycloheptanone 在 diiron nonacarbonyl 作用下， 以 甲苯 为溶剂， 生成 2,5-dimethyl-(1α,6α,2β,5β)-12-oxatricyclo-[4.4.1.1^2,5]dodec-3-en-11-one
  参考文献：
  名称：

  Structural characterization of unusually stable polycyclic ozonides

  摘要：

  The single crystal structure of seven tri- and tetracyclic ozonides derived from 8-oxabicycle[3.2.1]oct-6-en-3-ones have been characterized by X-ray diffraction method. Five ozonides (4, 5, 6,7 and 8) crystallize in the monoclinic crystal system with P2(1)/c space group. Compound 3 crystallize in the unusual centro-symmetric space group R (3) over barm, which represents similar to 0.04% of the total number of structures know. The supramolecular structure of 3 forms infinite channels in a hexagram fashion, resulting in a honeycomb-like structure. Semi-empirical (PM6) and density functional theory methods (DFT) with the B3LYP functional and the 6-31G(d) basis set were used to optimize the geometries and compute structural parameters (bond lengths, angles and dihedral angles) that could be compared to the refined crystal structure. The theoretical results show good agreements with the experimental structure. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.10.082

文献信息

• Structural characterization of unusually stable polycyclic ozonides
  作者：R.C. Cusati、U.A. Pereira、L.C.A. Barbosa、C.R.A. Maltha、José W.M. Carneiro、R.S. Corrêa、A.C. Doriguetto

  DOI：10.1016/j.molstruc.2014.10.082

  日期：2015.2

  The single crystal structure of seven tri- and tetracyclic ozonides derived from 8-oxabicycle[3.2.1]oct-6-en-3-ones have been characterized by X-ray diffraction method. Five ozonides (4, 5, 6,7 and 8) crystallize in the monoclinic crystal system with P2(1)/c space group. Compound 3 crystallize in the unusual centro-symmetric space group R (3) over barm, which represents similar to 0.04% of the total number of structures know. The supramolecular structure of 3 forms infinite channels in a hexagram fashion, resulting in a honeycomb-like structure. Semi-empirical (PM6) and density functional theory methods (DFT) with the B3LYP functional and the 6-31G(d) basis set were used to optimize the geometries and compute structural parameters (bond lengths, angles and dihedral angles) that could be compared to the refined crystal structure. The theoretical results show good agreements with the experimental structure. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis and Biological Evaluation of New Ozonides with Improved Plant Growth Regulatory Activity
  作者：Luiz C. A. Barbosa、Célia R. A. Maltha、Raphael C. Cusati、Róbson R. Teixeira、Filipe F. Rodrigues、Antônio A. Silva、Michael G. B. Drew、Fyaz M. D. Ismail

  DOI：10.1021/jf902540z

  日期：2009.11.11

  The iron oxyallyl carbocation generated from 2,7-dibromocycloheptanone was induced to undergo [4 + 3] cycloaddition reactions with various furans, affording a series of 12-oxatricyclo-[4.4.1.12,5]-dodec-3-en-11-one adducts. Similar methodology was used to prepare two additional cycloadducts using menthofuran and two homologous aliphatic dibromoketones. Dipolar cycloaddition of ozone to the adducts

  诱导从2,7-二溴环庚酮生成的氧氧基烯丙基碳正离子与各种呋喃进行[4 + 3]环加成反应，得到一系列的12-氧三环-[4.4.1.1 2,5 ] -dodec-3-en-11 -一个加合物。使用类似的方法，使用薄荷醇和两个同源的脂族二溴酮制备另外两个环加合物。臭氧与加合物的偶极环加成以可变的收率提供了相应的仲臭氧化物（即1,2,4-三氧戊环）。通过在B3LYP / 6-31 + G *水平上的量子力学研究了臭氧，研究了包括紧密接触的结构特征，这些紧密接触可能有助于增强臭氧的稳定性。这些臭氧化物及其相应的前体环加合物对双色高粱根系生长的影响和黄瓜在5.0×10评价-4摩尔大号-1。还评估了最活跃的环加合物和臭氧化物对杂草物种大叶番薯（Ipomoea grandifolia）和臂状臂锈菌（Brachiaria decumbens）的影响，并对结果进行了讨论。与先前在我们实验室中合成的臭氧化物相