((3,3-difluorocycloprop-1-en-1-yl)methyl)benzene | 1443207-45-1

• 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: ((3,3-difluorocycloprop-1-en-1-yl)methyl)benzene
• 英文别名: (3,3-Difluorocyclopropen-1-yl)methylbenzene；(3,3-difluorocyclopropen-1-yl)methylbenzene
• CAS: 1443207-45-1
• 化学式: C₁₀H₈F₂
• 分子量: 166.17
• InChiKey: CIMZMQYPWRUVDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((3,3-difluorocycloprop-1-en-1-yl)methyl)benzene 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以88%的产率得到2-benzylcycloprop-2-enone
  参考文献：
  名称：

  DBU-mediated transformation of arylmethylenecyclopropenes to alkylidenecyclopropanes

  摘要：

  An interesting DBU-mediated intramolecular isomerization of arylmethylenecyclopropenes 1 to alkylidenecyclopropanes (ACPs) has been described in this context. A variety of ACPs were obtained through a base-assisted manner in moderate to good yields under mild conditions with good stereoselectivities in most cases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.076
• 作为产物：
  描述：

  3-苯-1-丙炔 、 (三氟甲基)三甲基硅烷 在 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以62%的产率得到((3,3-difluorocycloprop-1-en-1-yl)methyl)benzene
  参考文献：
  名称：

  DBU-mediated transformation of arylmethylenecyclopropenes to alkylidenecyclopropanes

  摘要：

  An interesting DBU-mediated intramolecular isomerization of arylmethylenecyclopropenes 1 to alkylidenecyclopropanes (ACPs) has been described in this context. A variety of ACPs were obtained through a base-assisted manner in moderate to good yields under mild conditions with good stereoselectivities in most cases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.076

文献信息

• Modular, Concise, and Efficient Synthesis of Highly Functionalized 5-Fluoropyridazines by a [2 + 1]/[3 + 2]-Cycloaddition Sequence
  作者：Gaël Tran、Domingo Gomez Pardo、Tomoki Tsuchiya、Stefan Hillebrand、Jean-Pierre Vors、Janine Cossy

  DOI：10.1021/acs.orglett.5b01370

  日期：2015.7.17

  An easy access to 5-fluoropyridazines by a [2 + 1]/[3 + 2]-cycloaddition sequence between terminal alkynes, a difluorocarbene, and a diazo compound is reported. This approach does not necessitate the isolation of any intermediates, and a wide range of novel 5-fluoropyridazines was synthesized from readily available starting materials. Additionally, these compounds were used as a platform to access

  据报道，通过末端炔烃，二氟卡宾和重氮化合物之间的[2 +1] / [3 + 2]-环加成序列可轻松获得5-氟哒嗪。这种方法不需要分离任何中间体，并且从容易获得的起始原料合成了多种新型的5-氟哒嗪。此外，这些化合物还用作获取新型且高度多样化的哒嗪的平台。
• <i>Gem</i>-Difluorocyclopropenes as Versatile β-Monofluorinated Three-sp² Carbon Sources for Cp*Rh(III)-Catalyzed [4 + 3] Annulation: Experimental Development and Mechanistic Insight
  作者：Huiying Xu、Weijie Chen、Mengyao Bian、Hongtao Xu、Hui Gao、Ting Wang、Zhi Zhou、Wei Yi

  DOI：10.1021/acscatal.1c04508

  日期：2021.12.3

  oxidative addition/reductive elimination/C–F bond cleavage-enabled ring-scission involving the unprecedented olefinic C(sp2)–C(sp2) bond cleavage, has been deduced based on experimental and computational mechanistic studies. Taken together, our findings not only identified gem-difluorocyclopropenes as potent and efficient coupling partners for C–H activation development but also provided a sound basis

  Cp*Rh(III)-催化的N-甲氧基酰胺的[4 + 3] 环化，用于直接组装 7 编号的 2 H -azepin-2-one 骨架已经实现，gem-二氟环丙烯作为创新的 β-单氟化三sp 2碳源。发现嵌入各种官能团（包括 DNA 标记底物）的环状芳基酰胺或线性丙烯酰胺与已建立的 [4 + 3] 反应模式兼容。氧化还原中性的 Rh(III)-Rh(V)-Rh(III) 催化循环，特别是通过 HOAc 辅助的串联位点-/区域选择性氧化加成/还原消除/C-F 键断裂使环断裂，涉及前所未有的烯烃 C(sp 2 )–C(sp 2) 键断裂，是根据实验和计算力学研究推导出来的。综上所述，我们的研究结果不仅确定了gem-二氟环丙烯是 C-H 活化发展的有效偶联伙伴，而且还为过渡金属催化的 C-H 官能化与环丙烯和氟化学物质的有机整合提供了良好的基础。