1-methyl-2-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene | 1028333-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-2-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene
• CAS: 1028333-64-3
• 化学式: C₂₂H₂₄
• 分子量: 288.433
• InChiKey: PIGZRBFETRKXQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  氧杂蒽 、 1-methyl-2-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以31%的产率得到9-(4-methyl-1-phenyl-3-(prop-1-en-2-yl)-1-(o-tolyl)penta-1,3-dien-2-yl)-9H-xanthene
  参考文献：
  名称：

  Reactions of vinylidenecyclopropanes with xanthydrol and xanthene

  摘要：

  Vinylidenecyclopropanes undergo ring-opening reactions with xanthydrol in the presence of BF(3)center dot OEt(2) or with xanthene in the presence of DDQ at 0 degrees C in 1,2-dichloroethane to give the corresponding conjugate triene derivatives in moderate to good yields. Plausible reaction mechanisms have been discussed on the basis of previous literature and the control experiments. The further transformation of these trienes has been disclosed in DCE in the presence of BF(3)center dot OEt(2) along with a plausible reaction mechanism. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.004
• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 1-(2,2-dibromo-1-phenylcyclopropyl)-2-methylbenzene 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-methyl-2-(1-phenyl-2-(2,2,3,3-tetramethylcyclopropylidene)vinyl)benzene
  参考文献：
  名称：

  Brønsted Acid TfOH-Mediated [3 + 2] Cycloaddition Reactions of Diarylvinylidenecyclopropanes with Nitriles

  摘要：

  Diarylvinylidenecyclopropanes undergo a [3 + 2] cycloaddition reaction with MeCN in the presence of Bronsted acid TfOH to give the corresponding 3,4-dihydro-2H-pyn-ole derivatives 2 in moderate to excellent yields under reflux within a short time. As for the diarylvinylidenecyclopropane substrate containing a strongly electron-donating methoxy group on the benzene ring, the reaction leads to the formation of a different type of 3,4-dihydro-2H-pyrrole derivatives 4 under the same conditions.

  DOI：

  10.1021/jo800390c

文献信息

• Nd(OTf)₃-Catalyzed Cascade Reactions of Vinylidenecyclopropanes with Enynol: A New Method for the Construction of the 5-7-6 Tricyclic Framework and Its Scope and Limitations
  作者：Liang-Feng Yao、Min Shi

  DOI：10.1002/ejoc.200900660

  日期：2009.8

  We report in this paper a Lewis acid [Nd(OTf)(3)]-catalyzed protocol to construct compounds containing a 5-7-6 tricyclic framework in good yield from readily accessible starting materials vinylidenecyclopropanes (VDCPs) 1 and enynols 2a-c under mild conditions. Upon examination of the scope and limitations of this reaction, it was found that the corresponding highly functionalized cyclopentane derivatives

  我们在本文中报告了一种路易斯酸 [Nd(OTf)(3)] 催化的协议，该协议可以从易于获得的起始材料亚乙烯基环丙烷 (VDCPs) 1 和烯醇 2a-c 中以良好的收率构建含有 5-7-6 三环骨架的化合物在温和的条件下。通过检查该反应的范围和局限性，发现在相同条件下，VDCPs 1 和烯醇 2e 或二烯醇 2c 的反应可以以良好的产率形成相应的高度官能化的环戊烷衍生物。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Addition of diphenylphosphinodithioic acid and thioacetic acid with vinylidenecyclopropanes: reversed regioselectivities
  作者：Wei Li、Min Shi

  DOI：10.1016/j.tet.2009.06.090

  日期：2009.8

  The reaction of vinylidenecyclopropanes 1 with diphenylphosphinodithioic acid produces the adducts 3 in good to high yields in toluene upon heating at 100 °C within 1 h, whereas adducts 5 are obtained in excellent yields in reversed regioselectivity from the reaction of 1 with thioacetic acid under identical conditions. The radical reaction processes have been discussed on the basis of deuterium labeling

  亚乙烯基环丙烷1与二苯基次膦二硫代酸的反应在100°C下加热1小时后，在甲苯中生成高至高收率的加合物3，而在相同条件下1与硫代乙酸的反应则以极高的收率获得了高收率的加合物5。情况。在氘标记实验和在自由基抑制剂（TEMPO和BHT）或质子清除剂（DTBMP）存在下的对照实验的基础上，对自由基反应过程进行了讨论。
• Manganese(III)-mediated oxidative annulation of vinylidenecyclopropanes with 1,3-dicarbonyl compounds
  作者：Wei Yuan、Yin Wei、Min Shi

  DOI：10.1016/j.tet.2011.06.109

  日期：2011.9

  Manganese(III)-mediated oxidative annulation of vinylidenecyclopropanes with 1,3-dicarbonyl compounds in acetonitrile/acetic acid produces the corresponding functionalized dihydrofuran derivatives in moderate to good yields under mild conditions. The substrate scope has been examined and a plausible reaction mechanism has been also proposed on the basis of experimental results and previous literature

  锰（III）介导的亚乙烯基环丙烷与1,3-二羰基化合物在乙腈/乙酸中的氧化环化反应在温和的条件下以中等至良好的产率生成相应的官能化二氢呋喃衍生物。在实验结果和现有文献的基础上，研究了底物范围，并提出了合理的反应机理。
• Reactions of vinylidenecyclopropanes with xanthydrol and xanthene
  作者：Wei Yuan、Min Shi

  DOI：10.1016/j.tet.2010.07.004

  日期：2010.8

  Vinylidenecyclopropanes undergo ring-opening reactions with xanthydrol in the presence of BF(3)center dot OEt(2) or with xanthene in the presence of DDQ at 0 degrees C in 1,2-dichloroethane to give the corresponding conjugate triene derivatives in moderate to good yields. Plausible reaction mechanisms have been discussed on the basis of previous literature and the control experiments. The further transformation of these trienes has been disclosed in DCE in the presence of BF(3)center dot OEt(2) along with a plausible reaction mechanism. (C) 2010 Elsevier Ltd. All rights reserved.
• Brønsted Acid TfOH-Mediated [3 + 2] Cycloaddition Reactions of Diarylvinylidenecyclopropanes with Nitriles
  作者：Wei Li、Min Shi

  DOI：10.1021/jo800390c

  日期：2008.6.1

  Diarylvinylidenecyclopropanes undergo a [3 + 2] cycloaddition reaction with MeCN in the presence of Bronsted acid TfOH to give the corresponding 3,4-dihydro-2H-pyn-ole derivatives 2 in moderate to excellent yields under reflux within a short time. As for the diarylvinylidenecyclopropane substrate containing a strongly electron-donating methoxy group on the benzene ring, the reaction leads to the formation of a different type of 3,4-dihydro-2H-pyrrole derivatives 4 under the same conditions.