4-Pyrimidyldiphenylmethanol | 164738-49-2

• 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-Pyrimidyldiphenylmethanol
• 英文别名: diphenyl(pyrimidin-4-yl)methanol；I+/-,I+/--Diphenyl-4-pyrimidinemethanol
• CAS: 164738-49-2
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: CMDRMZSWNASLMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-Benzhydryl-pyrimidine 在 potassium tert-butylate 、 二甲基亚砜 作用下， 反应 1.0h， 以88%的产率得到4-Pyrimidyldiphenylmethanol
  参考文献：
  名称：

  Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation–Deuteration of Heterobenzylic Methylenes

  摘要：

  We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

  DOI：

  10.1021/acs.orglett.0c03108

文献信息

• Diazines 13: Metalation without Ortho-Directing Group - Functionalization of Diazines via Direct Metalation
  作者：Nelly Ple、Alain Turck、Karine Couture、Guy Queguiner

  DOI：10.1021/jo00117a033

  日期：1995.6

  The successful metalation of diazines without an ortho-directing group is described. In some cases, dimers were obtained. The metalation was optimal with LTMP if a 4-fold excess of metalating agent was used, with a very short metalation reaction time at -75 degrees C. This procedure was applied to pyrimidine, 2-substituted pyrimidines, pyridazine, and pyrazine, allowing for the synthesis of various monosubstituted diazines.
• Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation–Deuteration of Heterobenzylic Methylenes
  作者：Yonghai Liu、Yang Yu、Chengyu Sun、Yiwei Fu、Zhiguo Mang、Lei Shi、Hao Li

  DOI：10.1021/acs.orglett.0c03108

  日期：2020.10.16

  We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.