1-cyclopropyl-1-(3-trifluoromethylphenyl)ethene

• 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-cyclopropyl-1-(3-trifluoromethylphenyl)ethene
• 英文别名: 1-(1-Cyclopropylethenyl)-3-(trifluoromethyl)benzene
• 化学式: C₁₂H₁₁F₃
• 分子量: 212.215
• InChiKey: DDZJHTYLDRLQRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-1-(3-trifluoromethylphenyl)ethene 、 diiron nonacarbonyl 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 叔丁醇 、 二氯甲烷 为溶剂， 反应 12.5h， 以70%的产率得到3-(3-(trifluoromethyl)phenyl)cyclohex-2-enone
  参考文献：
  名称：

  Fe 2（CO）9介导的乙烯基环丙烷与CO的[5 + 1]环加成反应，合成α，β-环己烯酮

  摘要：

  已经开发出Fe 2（CO）9介导的乙烯基环丙烷（VCP）和CO与α，β-环己烯酮的[5 + 1]环加成反应。该反应可以耐受VCPsα位的芳基和脂族基团，而带有乙烯基或炔基取代基的VCP底物不是合适的。另外，如果芳基连接至底物的乙烯基部分，则该反应也可用于合成双环。与Fe（CO）5介导的[5 + 1]反应相比，便宜，安全的Fe 2（CO）9的使用和放弃光辐照条件是本方法的两个主要优点。

  DOI：

  10.1016/j.tet.2016.01.046
• 作为产物：
  描述：

  1-(cyclopropyl)vinyl diphenyl phosphate 、 3-(三氟甲基)苯硼酸 在 bis(1,5-cyclooctadiene)nickel (0) potassium phosphate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以56%的产率得到1-cyclopropyl-1-(3-trifluoromethylphenyl)ethene
  参考文献：
  名称：

  Investigations on the Suzuki−Miyaura and Negishi Couplings with Alkenyl Phosphates:  Application to the Synthesis of 1,1-Disubstituted Alkenes

  摘要：

  The development of versatile Suzuki-Miyaura and Negishi cross-couplings with nonactivated alkenyl phosphates and aromatic boronic acids or organozinc reagents was achieved in acceptable to good yields. A series of 1,1-disubstituted alkenes were synthesized using a combination of either Ni(COD)(2)/Cy3P/ K3PO4 or Pd(2)dba(3)/DPPF in THF. When working with alkenyl electrophiles in metal-catalyzed cross-couplings, this method lends itself as a less costly and more stable alternative to the corresponding triflate or nonaflate derivatives. In addition, initial studies are presented regarding an efficient 1,2-migration under Negishi coupling conditions.

  DOI：

  10.1021/jo070912k

文献信息

• Br-radical-mediated [3+2] annulation: synthesis of 2-bromomethyl-substituted alkenylcyclopentanes by the reaction of alkenylcyclopropanes with allyl bromides under photo irradiation
  作者：Takahide Fukuyama、Takashi Kippo、Kanako Hamaoka、Ilhyong Ryu

  DOI：10.1007/s11426-019-9595-0

  日期：2019.11

  A radical chain addition of allyl bromides 2 to alkenylcyclopropanes 1 resulted in [3+2] annulation to give 2-bromomethyl-alkenylcyclopentanes 3 in good yields (16 examples). In this reaction, two kinetically fast radical reactions, cyclopropylcarbinyl radical-ring-opening and 5-exo-radical cyclization, preceded the β-fragmentation of a bromine radical to make the formal cycloaddition possible.

  烯丙基溴2在链烯基环丙烷1上的自由基链加成导致[3 + 2]环化，以高收率得到2-溴甲基-烯基环戊烷3（16个实例）。在该反应中，先进行了两个动力学上快速的自由基反应，即环丙基羰基自由基的开环和5-外自由基的环化反应，然后再进行溴自由基的β片段化反应，从而使正式的环加成反应成为可能。
• Investigations on the Suzuki−Miyaura and Negishi Couplings with Alkenyl Phosphates:  Application to the Synthesis of 1,1-Disubstituted Alkenes
  作者：Anders L. Hansen、Jean-Philippe Ebran、Thomas M. Gøgsig、Troels Skrydstrup

  DOI：10.1021/jo070912k

  日期：2007.8.1

  The development of versatile Suzuki-Miyaura and Negishi cross-couplings with nonactivated alkenyl phosphates and aromatic boronic acids or organozinc reagents was achieved in acceptable to good yields. A series of 1,1-disubstituted alkenes were synthesized using a combination of either Ni(COD)(2)/Cy3P/ K3PO4 or Pd(2)dba(3)/DPPF in THF. When working with alkenyl electrophiles in metal-catalyzed cross-couplings, this method lends itself as a less costly and more stable alternative to the corresponding triflate or nonaflate derivatives. In addition, initial studies are presented regarding an efficient 1,2-migration under Negishi coupling conditions.
• Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α, β-cyclohexenones
  作者：Cheng-Hang Liu、Zhe Zhuang、Sritama Bose、Zhi-Xiang Yu

  DOI：10.1016/j.tet.2016.01.046

  日期：2016.6

  A Fe2(CO)9-mediated [5+1] cycloaddition of vinylcyclopropanes (VCPs) and CO to α, β-cyclohexenones has been developed. The reaction can tolerate aryl and aliphatic groups at the α-position of VCPs, while VCP substrates with vinyl or alkynyl substitutions are not suitable ones. In addition, this reaction can also be used to synthesize bicyclic rings if an aryl group is attached to the vinyl moiety of

  已经开发出Fe 2（CO）9介导的乙烯基环丙烷（VCP）和CO与α，β-环己烯酮的[5 + 1]环加成反应。该反应可以耐受VCPsα位的芳基和脂族基团，而带有乙烯基或炔基取代基的VCP底物不是合适的。另外，如果芳基连接至底物的乙烯基部分，则该反应也可用于合成双环。与Fe（CO）5介导的[5 + 1]反应相比，便宜，安全的Fe 2（CO）9的使用和放弃光辐照条件是本方法的两个主要优点。