M-1-(2'-benzyloxy-4',6'-dimethylphenyl)-2-hydroxymethylnaphthalene | 155998-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: M-1-(2'-benzyloxy-4',6'-dimethylphenyl)-2-hydroxymethylnaphthalene
• 英文别名: [1-(2,4-Dimethyl-6-phenylmethoxyphenyl)naphthalen-2-yl]methanol；[1-(2,4-dimethyl-6-phenylmethoxyphenyl)naphthalen-2-yl]methanol
• CAS: 155998-20-2
• 化学式: C₂₆H₂₄O₂
• 分子量: 368.475
• InChiKey: YRFGUNWCQXUPJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  M-1-(2'-benzyloxy-4',6'-dimethylphenyl)-2-hydroxymethylnaphthalene 在 1,2-二溴四氯乙烷 、 三苯基膦 、 甲胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 M-1-(2'-benzyloxy-4',6'-dimethylphenyl)-2-(N-methylaminomethyl)naphthalene
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts [1]

  摘要：

  The synthesis of atropo-enantiomerically pure aminomethyl and hydroxymethyl substituted biaryls derivatives M-2 and M-3 (and, optionally, their enantiomers), by dynamic kinetic resolution of a racemic lactone precursor, is described. Their application as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes leads to excellent enantiomeric ratios of up to 99:1 and high chemical yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00020-2
• 作为产物：
  描述：

  2-(2-(hydroxymethyl)naphthalen-1-yl)-3,5-dimethylphenol 在 lithium aluminium tetrahydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 13.0h， 生成 M-1-(2'-benzyloxy-4',6'-dimethylphenyl)-2-hydroxymethylnaphthalene
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts [1]

  摘要：

  The synthesis of atropo-enantiomerically pure aminomethyl and hydroxymethyl substituted biaryls derivatives M-2 and M-3 (and, optionally, their enantiomers), by dynamic kinetic resolution of a racemic lactone precursor, is described. Their application as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes leads to excellent enantiomeric ratios of up to 99:1 and high chemical yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00020-2

文献信息

• Bringmann, Gerhard; Hartung, Thomas, Liebigs Annalen der Chemie, 1994, # 3, p. 313 - 316
  作者：Bringmann, Gerhard、Hartung, Thomas

  DOI：——

  日期：——
• Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts [1]
  作者：Gerhard Bringmann、Matthias Breuning

  DOI：10.1016/s0957-4166(98)00020-2

  日期：1998.2

  The synthesis of atropo-enantiomerically pure aminomethyl and hydroxymethyl substituted biaryls derivatives M-2 and M-3 (and, optionally, their enantiomers), by dynamic kinetic resolution of a racemic lactone precursor, is described. Their application as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes leads to excellent enantiomeric ratios of up to 99:1 and high chemical yields. (C) 1998 Elsevier Science Ltd. All rights reserved.