(±)-2,4-diiodo-1-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene | 1398038-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (±)-2,4-diiodo-1-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene
• CAS: 1398038-77-1
• 化学式: C₁₇H₁₆I₂O
• 分子量: 490.122
• InChiKey: VVTGWVWOXLSRKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (±)-2,4-diiodo-1-((3-methyl-1-phenylbut-3-en-1-yl)oxy)benzene 在 二(三叔丁基膦)钯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以82%的产率得到
  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
• 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 (±)-2,4-diiodo-1-((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

• Harnessing Reversible Oxidative Addition: Application of Diiodinated Aromatic Compounds in the Carboiodination Process
  作者：David A. Petrone、Matthias Lischka、Mark Lautens

  DOI：10.1002/anie.201304923

  日期：2013.9.27

  simultaneous convergent intramolecular carboiodination/intermolecular Heck reaction of various diiodoarenes were developed. The ability of the Pd0/QPhos catalyst/ligand combination to undergo reversible oxidative addition allows these reactions to proceed well, thus increasing both the appeal and utility of this class of substrates in site‐selective cross‐coupling reactions.

  I为I：开发了各种二碘代芳烃的分子内碳碘化和同时收敛的分子内碳碘化/分子间Heck反应的条件。Pd 0 / QPhos催化剂/配体组合进行可逆氧化加成的能力使这些反应顺利进行，从而提高了这类底物在定点交叉偶联反应中的吸引力和实用性。