(±)-2-methyl-1-(2-(trifluoromethyl)phenyl)prop-2-en-1-ol | 1398038-87-3

• 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: (±)-2-methyl-1-(2-(trifluoromethyl)phenyl)prop-2-en-1-ol
• 英文别名: 2-Methyl-1-[2-(trifluoromethyl)phenyl]prop-2-en-1-ol；2-methyl-1-[2-(trifluoromethyl)phenyl]prop-2-en-1-ol
• CAS: 1398038-87-3
• 化学式: C₁₁H₁₁F₃O
• 分子量: 216.203
• InChiKey: ZZHCZBXBEPLVLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-2-methyl-1-(2-(trifluoromethyl)phenyl)prop-2-en-1-ol 在 二(三叔丁基膦)钯 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 21.0h， 生成 (±)-4-(iodomethyl)-4-methyl-3-(2-(trifluoromethyl)phenyl)isochroman
  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：

  邻三氟甲基苯甲醛 、 异丙烯基溴化镁 以 四氢呋喃 为溶剂， 反应 0.33h， 以91%的产率得到(±)-2-methyl-1-(2-(trifluoromethyl)phenyl)prop-2-en-1-ol
  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

• Functionalized Chromans and Isochromans via a Diastereoselective Pd(0)-Catalyzed Carboiodination
  作者：David A. Petrone、Hasnain A. Malik、Antonin Clemenceau、Mark Lautens

  DOI：10.1021/ol302111y

  日期：2012.9.21

  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.