4-(Diphenylmethyl)quinoline | 5632-20-2

• 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-(Diphenylmethyl)quinoline
• 英文别名: 4-benzhydryl-quinoline；4-Benzhydryl-chinolin；4-benzhydrylquinoline
• CAS: 5632-20-2
• 化学式: C₂₂H₁₇N
• 分子量: 295.384
• InChiKey: FNCQDPQBFBTXNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(Diphenylmethyl)quinoline 在 potassium tert-butylate 、 二甲基亚砜 作用下， 反应 0.5h， 以83%的产率得到diphenyl(quinolin-4-yl)methanol
  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
• 作为产物：
  描述：

  4-甲基喹啉 、 氯苯 在 氨 、 potassium amide 作用下， 生成 4-(Diphenylmethyl)quinoline
  参考文献：
  名称：

  液氨中一些酰胺化的钾活化的苯基化反应。

  摘要：

  DOI：

  10.1021/jo01171a008

文献信息

• The Superacid Induced Condensation of Quinolinecarboxaldehydes with Arenes
  作者：Douglas A. Klumpp、Andre Jones、Siufu Lau、Sarah de Leon、Manuel Garza

  DOI：10.1055/s-2000-6322

  日期：——

  A variety of quinolinecarboxaldehydes have been reacted with arenes in the Brönsted superacid, CF3SO3H (triflic acid) to give condensation products in good to excellent yields (52-99%). The quinolinecarboxaldehydes are significantly more reactive than 2-naphthalenecarboxaldehyde. It is proposed that the increased reactivity is due to the formation of dicationic, electrophilic intermediates.

  多种喹啉羧醛与芳烃在Brönsted超酸CF3SO3H（氟烷酸）中反应，得到的缩合产物产率良好至优秀（52-99%）。与2-萘甲醛相比，喹啉羧醛的反应性显著更强。提出增加的反应性是由于形成了二阳离子电性中间体。
• 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.
• SOME POTASSIUM AMIDE-ACTIVATED PHENYLATIONS IN LIQUID AMMONIA (1)
  作者：PHILIP H. DIRSTINE、F. W. BERGSTROM

  DOI：10.1021/jo01171a008

  日期：1946.1