(±)-1-iodo-2-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene | 1398038-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (±)-1-iodo-2-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene
• 英文别名: 1-iodo-2-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene；1-Iodo-2-(3-methyl-1-phenylbut-3-enoxy)benzene
• CAS: 1398038-65-7
• 化学式: C₁₇H₁₇IO
• 分子量: 364.226
• InChiKey: RKBYGJKZPYRGSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (±)-1-iodo-2-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 双氧水 、 potassium acetate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 rac-[(2R,4S)-4-methyl-2-phenylchroman-4-yl]methanol
  参考文献：
  名称：

  Diastereoselective Pd-Catalyzed Domino Heck/Arylborylation Sequence Forming Borylated Chromans

  摘要：

  A diastereoselective palladium-catalyzed domino Heck/arylborylation of aryl iodides yielding an alkylboronate containing a chroman is reported. The generated alkylpalladium(II) intermediate is intercepted with bis(pinacolato)diboron (B(2)pin(2)) in good yield as a single diastereomer.

  DOI：

  10.1055/s-0035-1561567
• 作为产物：
  描述：

  苯甲醛 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.33h， 生成 (±)-1-iodo-2-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene
  参考文献：
  名称：

  Functionalized Chromans and Isochromans via a Diastereoselective Pd(0)-Catalyzed Carboiodination

  摘要：

  A diastereoselective approach to isochromans and chromans via Pd(0)-catalyzed carboiodination is reported. The transformations using this methodology display excellent yields and diastereoselectivities as well as broad functional group compatibility. The selectivity observed in these cyclizations, forming isochroman or chroman targets, is postulated to originate from the minimization of A(1,2) strain and axial axial interactions, respectively. This method has also been used to highlight the concept of reversible oxidative addition to carbon iodine bonds in polyiodinated substrates.

  DOI：

  10.1021/ol302111y

文献信息

• Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles
  作者：Marco Wollenburg、Jonathan Bajohr、Austin D. Marchese、Andrew Whyte、Frank Glorius、Mark Lautens

  DOI：10.1021/acs.orglett.0c01169

  日期：2020.5.1

  A method for the palladium-catalyzed disilylation and digermanylation of aryl halides bearing a tethered alkene has been developed. The mechanism is thought to proceed via Heck-type cyclization, followed by C-H activation, resulting in a reactive fused-palladacycle. A wide variety of disilylated and digermanylated heterocycles are obtained from readily available aryl halides in high yields with various

  已经开发了钯催化带有链状烯烃的芳基卤化物的二甲硅烷基化和二锗烷基化的方法。据认为，该机制是通过Heck型环化进行的，然后是CH活化，从而导致反应性稠合Palladacycle。从容易获得的具有各种官能团的芳基卤化物中获得了各种各样的二甲硅烷基化和二锗烷基化的杂环。此外，开发的协议被证明是高度非对映选择性的。