1-(2-methyl-2-phenylvinylidene)-2,2,3,3-tetramethylcyclopropane | 137451-98-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(2-methyl-2-phenylvinylidene)-2,2,3,3-tetramethylcyclopropane
• CAS: 137451-98-0
• 化学式: C₁₆H₂₀
• 分子量: 212.335
• InChiKey: ONWBAGSXWKWMRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  1-(2-methyl-2-phenylvinylidene)-2,2,3,3-tetramethylcyclopropane 在 [Au(Cl)PPh₃] 、 silver trifluoromethanesulfonate 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 0.17h， 以60%的产率得到1,1,4-Trimethyl-2-propan-2-ylidenenaphthalene
  参考文献：
  名称：

  Gold(I)-Catalyzed Intramolecular Rearrangement of Vinylidenecyclopropanes

  摘要：

  Vinylidenecyclopropanes 1 can undergo intramolecular rearrangement to give the corresponding functionalized 1,2-dihydronaphthalenes in the presence of gold catalyst under mild conditions. A plausible rearrangement mechanism has been proposed on the basis of control experiments.

  DOI：

  10.1021/jo801579b
• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 、 (2,2-dibromo-1-methylcyclopropyl)benzene 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-(2-methyl-2-phenylvinylidene)-2,2,3,3-tetramethylcyclopropane
  参考文献：
  名称：

  制备多取代环戊烷的催化方法：[3 + 2]偏二酰亚胺催化的亚乙烯基环丙烷与活化烯烃的环加成反应

  摘要：

  [3 + 2]亚乙烯基环丙烷（VDCPs）与缺电子烯烃如甲基乙烯基酮（MVK）和丙烯醛的环加成反应在催化量的三氟甲基酰亚胺（Tf 2 NH）的存在下平稳进行，得到相应的官能团环戊烷的收率高到高。

  DOI：

  10.1021/jo802294s

文献信息

• Cyclopropanation of Vinylidenecyclopropanes. Synthesis of 1-(Dihalomethylene)spiropentanes
  作者：Hajime Maeda、Takayoshi Hirai、Akira Sugimoto、Kazuhiko Mizuno

  DOI：10.1021/jo0301595

  日期：2003.10.1

  amount of 1-(dihalomethylene)spiropentanes. The efficiency of the thermal rearrangement from the cyclopropylidenecyclopropanes to the 1-(dihalomethylene)spiropentane derivatives depended on the substituents and the reaction temperature. Reaction of diarylvinylidenecyclopropanes with diphenylcarbene and phenylthiocarbene gave the corresponding spiropentane derivatives. This type of thermal rearrangement

  描述了通过亚环戊烯通过亚乙烯基环丙烷的丙烷丙烷化而生成的环亚丙基环丙烷来合成1-（二卤代亚甲基）螺戊烷。二芳基亚乙烯基亚环丙烷与二溴卡宾和二氯卡宾的反应以高收率独家得到1-（二卤代亚甲基）螺戊烷。单芳基亚乙烯基环丙烷与二卤代卡宾的反应得到环丙叉基环丙烷为主要产物，并形成少量的1-（二卤代亚甲基）螺戊烷。从环亚丙基环丙烷到1-（二卤代亚甲基）螺戊烷衍生物的热重排效率取决于取代基和反应温度。二芳基亚乙烯基亚环丙烷与二苯基卡宾和苯硫代卡宾的反应得到相应的螺戊烷衍生物。
• 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。
• Lewis Acid Catalyzed Reactions of Vinylidenecyclopropanes with Activated Carbon−Oxygen Double Bond:  A Facile Synthetic Protocol for Functionalized Tetrahydrofuran and 3,6-Dihydropyran Derivatives
  作者：Jian-Mei Lu、Min Shi

  DOI：10.1021/jo702518u

  日期：2008.3.1

  A number of functionalized tetrahydrofuran and 3,6-dihydropyran derivatives are prepared selectively in moderate to good yields by the reactions of vinylidenecyclopropanes with activated carbonyl compounds in the presence of Lewis acid.

  在路易斯酸存在下，通过亚乙烯基环丙烷与活化的羰基化合物的反应，以中等至良好的产率选择性地制备许多官能化的四氢呋喃和3，6-二氢吡喃衍生物。
• Facile Synthesis of Tetrahydrofurans from Cycloadditions of Vinylidenecyclopropanes with Aldehydes and Further Tunable Transformations for the Construction of Furan, Indene, and Benzo[<i>c</i>]fluorene Derivatives
  作者：Chenliang Su、Xian Huang、Qingyang Liu、Xin Huang

  DOI：10.1021/jo901836v

  日期：2009.11.6

  The cycloadditions of vinylidenecyclopropanes with aldehydes for the synthesis of tetrahydrofurans are detailed in this paper. The obtained polysubstituted tetrahydrofurans could serve as versatile intermediates to selectively produce furan, indene, and benzo[c]fluorene derivatives depending on the substituents at the tetrahydrofurans’ rings and the varied reaction conditions, which clearly exhibit

  本文详细介绍了亚乙烯基亚环丙烷与醛的环加成反应，以合成四氢呋喃。取决于四氢呋喃环上的取代基和变化的反应条件，所获得的多取代四氢呋喃可作为通用中间体选择性地生产呋喃，茚和苯并[ c ]芴衍生物，这清楚地展示了对四氢呋喃合成应用的见识。已经详细讨论了这些转换的范围，局限性和机制。有吸引力的是，亚乙烯基亚环丙烷与醛的这些环加成反应以及环加合物的进一步转化为构建各种中型和大型环稠合四氢呋喃，呋喃和苯并[]提供了有效的方法。c ]芴衍生物。
• An efficient synthesis of polysubstituted tetrahydrofuran and indene derivatives via the Lewis acid-mediated cycloadditions of VCPs with aldehydes
  作者：Chenliang Su、QingYang Liu、Yong Ni、Xian Huang

  DOI：10.1016/j.tetlet.2009.05.038

  日期：2009.7

  A variety of polysubstituted tetrahydrofuran and indene derivatives were prepared in moderate to excellent yields via the cycloadditions of vinylidenecyclopropanes with common aldehydes in the presence of Lewis acid. The polysubstituted tetrahydrofuran 3 Could undergo further trans formations to the indene product 4 and furan derivatives 5. (C) 2009 Elsevier Ltd. All rights reserved.