1-cyclopropyl-4-vinylbenzene | 19824-39-6

• 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-4-vinylbenzene
• 英文别名: 4-Cyclopropyl-styrol；1-Cyclopropyl-4-ethenylbenzene；1-cyclopropyl-4-ethenylbenzene
• CAS: 19824-39-6
• 化学式: C₁₁H₁₂
• 分子量: 144.216
• InChiKey: HDYQUNRICCEOOP-UHFFFAOYSA-N

物化性质

• 沸点：
  105-106 °C(Press: 12 Torr)
• 密度：
  0.9628 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-cyclopropyl-4-vinylbenzene 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 4-环丙基苯甲酸
  参考文献：
  名称：

  Discovery of Potent 3,5-Diphenyl-1,2,4-oxadiazole Sphingosine-1-phosphate-1 (S1P₁) Receptor Agonists with Exceptional Selectivity against S1P₂ and S1P₃

  摘要：

  A class of 3,5-diphenyl-1,2,4-oxadiazole based compounds have been identified as potent sphingosine-1-phosphate-1 (S1P(1)) receptor agonists with minimal affinity for the S1P(2) and S1P3 receptor subtypes. Analogue 26 (S1P(1) IC50 = 0.6 nM) has an excellent pharmacokinetics profile in the rat and dog and is efficacious in a rat skin transplant model, indicating that S1P(3) receptor agonism is not a component of inummosuppressive efficacy.

  DOI：

  10.1021/jm0503244
• 作为产物：
  描述：

  1-(4-环丙基苯基)乙酮 生成 1-cyclopropyl-4-vinylbenzene
  参考文献：
  名称：

  Levina,R.Ya. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 358 - 363

  摘要：

  DOI：

文献信息

• Copper‐Catalyzed Chemo‐ and Enantioselective Radical 1,2‐Carbophosphonylation of Styrenes
  作者：Huan Zhou、Li‐Wen Fan、Yang‐Qing Ren、Li‐Lei Wang、Chang‐Jiang Yang、Qiang‐Shuai Gu、Zhong‐Liang Li、Xin‐Yuan Liu

  DOI：10.1002/anie.202218523

  日期：2023.3.20

  Copper-catalyzed chemo- and enantioselective radical 1,2-carbophosphonylation of styrenes from readily available alkyl halides and dialkyl phosphites is developed. The key to the success of the strategy lies in not only the proper choice of phosphorus reagents to suppress the reverse chemoselectivity but also the utilization of a chiral N,N,N-ligand to forge chiral C(sp3)−P bond.

  开发了铜催化的化学选择性和对映选择性自由基 1,2-碳膦酰基化苯乙烯从容易获得的烷基卤化物和亚磷酸二烷基酯。该策略成功的关键不仅在于正确选择磷试剂以抑制反向化学选择性，还在于利用手性N,N,N-配体形成手性 C(sp 3 )−P 键。
• Rhodium‐Catalyzed Regio‐ and Diastereoselective [3+2] Cycloaddition of <i>gem</i>‐Difluorinated Cyclopropanes with Internal Olefins
  作者：Yaxin Zeng、Ying Xia

  DOI：10.1002/anie.202307129

  日期：2023.8.7

  A rhodium-catalyzed [3+2] cycloaddition reaction between readily available gem-difluorinated cyclopropanes and internal olefins has been developed, providing a wide range of multisubstituted gem-difluorinated cyclopentanes. This reaction shows an example where the “CF2” motif can be kept upon ring extension. The process is atom-economic and allows to reach numerous gem-difluorinated cyclopentanes with

  已经开发了易于获得的偕二氟化环丙烷和内烯烃之间的铑催化[3+2]环加成反应，提供了多种多取代偕二氟化环戊烷。该反应显示了“CF 2 ”基序可以在环延伸时保留的例子。该方法是原子经济的，并且可以得到许多具有良好区域选择性和非对映选择性的偕二氟化环戊烷。
• Rhodium‐Catalyzed Enantio‐ and Regioselective Allylation of Indoles with gem‐Difluorinated Cyclopropanes
  作者：Hui Yang、Yaxin Zeng、Xiangyu Song、Lin Che、Zhong‐Tao Jiang、Gang Lu、Ying Xia

  DOI：10.1002/anie.202403602

  日期：2024.5.27

  The first enantioselective allylation of indoles with gem-difluorinated cyclopropanes is developed under rhodium catalysis. The reaction shows exceptional branched regioselectivity and excellent enantioselectivity with a bulky ligand, which provides an efficient route to enantioenriched C2 and C3 fluoroallylated indoles with wide substrate scope and good functional group tolerance.

  在铑催化下开发了吲哚与偕二氟化环丙烷的第一个对映选择性烯丙基化反应。该反应显示出优异的支链区域选择性和对大配体的优异对映选择性，这为获得对映体富集的 C2 和 C3 氟烯丙基化吲哚提供了一条有效的途径，具有广泛的底物范围和良好的官能团耐受性。