(R)-2-((4-(methoxymethoxy)phenyl)(piperidin-1-yl)methyl)phenol | 1357005-81-2

• 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: (R)-2-((4-(methoxymethoxy)phenyl)(piperidin-1-yl)methyl)phenol
• 英文别名: 2-[(R)-[4-(methoxymethoxy)phenyl]-piperidin-1-ylmethyl]phenol
• CAS: 1357005-81-2
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: BVVKSYJYKJVSNP-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌啶 、 4-(甲氧基甲氧基)苯硼酸 、 水杨醛 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(((R)-2,2'-dihydroxy-1,1'-binaphthyl-3-yl)methylamino)cyclohexyl)thiourea 作用下， 以 甲基叔丁基醚 为溶剂， 反应 120.0h， 以65%的产率得到(R)-2-((4-(methoxymethoxy)phenyl)(piperidin-1-yl)methyl)phenol
  参考文献：
  名称：

  Enantioselective Organocatalytic Three-Component Petasis Reaction among Salicylaldehydes, Amines, and Organoboronic Acids

  摘要：

  The catalytic enantioselective three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids with a newly designed thiourea-binol catalyst is presented. A broad range of alkylaminophenols can be obtained in good yield (up to 92%) and good to high enantioselectivity (up to 95% ee). A possible reaction pathway for this catalytic enantioselective Petasis reaction is tentatively proposed.

  DOI：

  10.1021/ol203109a

文献信息

• Enantioselective Petasis reaction among salicylaldehydes, amines, and organoboronic acids catalyzed by BINOL
  作者：Wen-Yong Han、Jian Zuo、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2012.11.043

  日期：2013.1

  The catalytic enantioselective three-component Petasis reaction among salicylaldehydes, amines, and organoboronic acids has been developed with readily available chiral BINOL as catalyst. Various salicylaldehydes, secondary amines, and organoboronic acids were found to be suitable substrates for the reaction. A broad range of desired alkylaminophenol products were obtained in good yields (up to 87%) and moderate to good enantioselectivities (up to 86% ee). (c) 2012 Elsevier Ltd. All rights reserved.