2-bromo-4-methoxy-1-(2-methylallyloxy)benzene | 1333120-09-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-4-methoxy-1-(2-methylallyloxy)benzene
• 英文别名: 2-Bromo-4-methoxy-1-(2-methylprop-2-enoxy)benzene；2-bromo-4-methoxy-1-(2-methylprop-2-enoxy)benzene
• CAS: 1333120-09-4
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: MSOPVIRTUQIUNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4-methoxy-1-(2-methylallyloxy)benzene 在 Pd(Q-Phos)2 、 potassium iodide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以92%的产率得到3-iodomethyl-5-methoxy-3-methyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes

  摘要：

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.

  DOI：

  10.1021/ja206099t
• 作为产物：
  描述：

  2-溴-4-甲氧基苯酚 、 3-氯-2-甲基丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-4-methoxy-1-(2-methylallyloxy)benzene
  参考文献：
  名称：

  基于钯的能动重排实现烯烃的表观 6-内触发碳氟化

  摘要：

  逆转本征环化模式。在 Selectfluor 2存在下，Pd 催化的 2-(2-烷基烯丙氧基) 苯基硼酸衍生物环化提供苯并三氢呋喃3，同时生成叔烷基氟化物功能。5 - exo -trig carbopalladation 提供 Pd II中间体A，其氧化为 Pd IV，然后进行 1,2-芳基/Pd IV变色重排和 C−F 键形成还原消除，得到苯并三氢呋喃3。

  DOI：

  10.1002/anie.202211470

文献信息

• Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes
  作者：Stephen G. Newman、Jennifer K. Howell、Norman Nicolaus、Mark Lautens

  DOI：10.1021/ja206099t

  日期：2011.9.28

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.
• Apparent 6‐ <i>endo‐</i> trig Carbofluorination of Alkenes Enabled by Palladium‐Based Dyotropic Rearrangement
  作者：Jing Gong、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202211470

  日期：2022.12.12

  cyclization mode. Pd-catalyzed cyclization of 2-(2-alkylallyloxy)phenyl boronic acid derivatives in the presence of Selectfluor 2 provides chromanes 3 with concurrent generation of a tertiary alkyl fluoride function. A 5-exo-trig carbopalladation affords PdII intermediate A whose oxidation to PdIV followed by 1,2-aryl/PdIV dyotropic rearrangement and C−F bond-forming reductive elimination affords chromane

  逆转本征环化模式。在 Selectfluor 2存在下，Pd 催化的 2-(2-烷基烯丙氧基) 苯基硼酸衍生物环化提供苯并三氢呋喃3，同时生成叔烷基氟化物功能。5 - exo -trig carbopalladation 提供 Pd II中间体A，其氧化为 Pd IV，然后进行 1,2-芳基/Pd IV变色重排和 C−F 键形成还原消除，得到苯并三氢呋喃3。