4-(2-bromoethynyl)-1-fluoro-2-methylbenzene | 1211318-55-6

• 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: 4-(2-bromoethynyl)-1-fluoro-2-methylbenzene
• CAS: 1211318-55-6
• 化学式: C₉H₆BrF
• 分子量: 213.049
• InChiKey: SIGQSRPRVNIPPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2-bromoethynyl)-1-fluoro-2-methylbenzene 在 potassium phosphate 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 叔丁基锂 作用下， 以 乙醚 、 甲苯 、 正戊烷 为溶剂， 反应 38.0h， 生成 N-tert-butoxycarbonyl-3-(3-methyl-4-fluorophenyl)indole
  参考文献：
  名称：

  Intramolecular Carbocupration of N-Aryl-ynamides: A Modular Indole Synthesis

  摘要：

  A modular indole synthesis based on an intramolecular 5-endo-dig carbocupration starting from readily available N-aryl-ynamides Is reported. A variety of ynamides are converted to indoles in moderate to good yields and with varying substitution pattern on the indole ring. This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions.

  DOI：

  10.1021/ol4013298
• 作为产物：
  描述：

  4-乙炔基-1-氟-2-甲苯 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 生成 4-(2-bromoethynyl)-1-fluoro-2-methylbenzene
  参考文献：
  名称：

  Intramolecular Carbocupration of N-Aryl-ynamides: A Modular Indole Synthesis

  摘要：

  A modular indole synthesis based on an intramolecular 5-endo-dig carbocupration starting from readily available N-aryl-ynamides Is reported. A variety of ynamides are converted to indoles in moderate to good yields and with varying substitution pattern on the indole ring. This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions.

  DOI：

  10.1021/ol4013298

文献信息

• Copper-catalysed bromoalkynylation of arynes
  作者：Takami Morishita、Hiroto Yoshida、Joji Ohshita

  DOI：10.1039/b919301d

  日期：——

  Arynes were found to be inserted into a C(sp)–Br σ-bond of bromoalkynes in the presence of a copper catalyst, giving (alkynyl)bromoarenes in a straightforward manner.

  发现是在铜催化剂存在下，炔基化合物可以插入溴烷烃中的C(sp)–Br σ键，从而简单地合成(炔基)溴芳烃。
• Enantioconvergent Reductive C(sp)−C(sp ³ ) Cross‐Coupling to Access Chiral α‐Alkynyl Phosphonates Under Dual Nickel/Photoredox Catalysis
  作者：Hepan Wang、Xiaoqiang Wu、Tao XU

  DOI：10.1002/anie.202218299

  日期：——

  carbon-carbon bond formation to forge phosphonates with an α-chiral carbon center through C(sp3)−C(sp3) and C(sp2)−C(sp3) couplings has been successful. However, the enantioselective C(sp)−C(sp3) coupling has not yet been disclosed. Reported herein is an unprecedented enantioconvergent cross-coupling of alkynyl bromides and α-bromo phosphonates to deliver chiral α-alkynyl phosphonates.

  过渡金属催化的不对称碳-碳键形成通过 C(sp 3 )−C(sp 3 ) 和 C(sp 2 )−C(sp 3 ) 偶联形成具有 α-手性碳中心的膦酸酯已取得成功。然而，尚未公开对映选择性C(sp)-C(sp 3 )偶联。本文报道了炔基溴化物和 α-溴膦酸酯前所未有的对映收敛交叉偶联，以提供手性 α-炔基膦酸酯。
• Intramolecular Carbocupration of <i>N</i>-Aryl-ynamides: A Modular Indole Synthesis
  作者：Wafa Gati、François Couty、Taoufik Boubaker、Mohamed M. Rammah、Mohamed B. Rammah、Gwilherm Evano

  DOI：10.1021/ol4013298

  日期：2013.6.21

  A modular indole synthesis based on an intramolecular 5-endo-dig carbocupration starting from readily available N-aryl-ynamides Is reported. A variety of ynamides are converted to indoles in moderate to good yields and with varying substitution pattern on the indole ring. This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions.