M-1-(2'-benzyloxy-4',6'-dimethylphenyl)-2-(N-methylaminomethyl)naphthalene | 210490-10-1

• 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-(N-methylaminomethyl)naphthalene
• CAS: 210490-10-1
• 化学式: C₂₇H₂₇NO
• 分子量: 381.517
• InChiKey: VIGULGWAOIYTCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  M-1-(2'-benzyloxy-4',6'-dimethylphenyl)-2-(N-methylaminomethyl)naphthalene 在 三氯化硼 作用下， 以 正己烷 为溶剂， 反应 0.67h， 以99%的产率得到M-1-(2'-hydroxy-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 、 1,2-二溴四氯乙烷 、 caesium carbonate 、 三苯基膦 、 甲胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 14.5h， 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

文献信息

• Synthesis of Enantiopure Axially Chiral <i>C</i>₃-Symmetric Tripodal Ligands and Their Application as Catalysts in the Asymmetric Addition of Dialkylzinc to Aldehydes
  作者：Gerhard Bringmann、Robert-Michael Pfeifer、Christian Rummey、Kristina Hartner、Matthias Breuning

  DOI：10.1021/jo034697t

  日期：2003.9.1

  The enantioselective synthesis of a novel-type C(3)-symmetric tripodal ligand that is composed of a central mesitylene-derived core and three functionalized, axially chiral biaryl subunits is described. The triol (M,M,M)-3 is a suitable catalyst for the enantioselective addition of dialkylzinc to various aromatic aldehydes with asymmetric inductions of up to 98% ee.

  描述了对映体选择性的新型C（3）对称三脚架配体的组成，该配体由中央均三甲苯基衍生的核心和三个功能化的轴向手性联芳基亚基组成。三醇（M，M，M）-3是用于将二烷基锌对映选择性加成到各种芳香醛中的合适催化剂，不对称诱导率最高为98％ee。
• 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.