(S,R)-3-methyl-2-(1-phenethyl-2-phenyl-but-3-enylamino)-phenol | 1000026-17-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (S,R)-3-methyl-2-(1-phenethyl-2-phenyl-but-3-enylamino)-phenol
• 英文别名: 2-[[(3S,4R)-1,4-diphenylhex-5-en-3-yl]amino]-3-methylphenol
• CAS: 1000026-17-4
• 化学式: C₂₅H₂₇NO
• 分子量: 357.495
• InChiKey: AJUXJUWWTCGPMB-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4S,5S)-2-chloro-3,4-dimethyl-5-phenyl-2-[(E)-3-phenylprop-2-enyl]-1,3,2-oxazasilolidine 、 以 二氯甲烷 为溶剂， 反应 36.0h， 以53%的产率得到(S,R)-3-methyl-2-(1-phenethyl-2-phenyl-but-3-enylamino)-phenol
  参考文献：
  名称：

  Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch

  摘要：

  The first general method for the enantioselective cinnamylation of aldimines is reported. The method utilizes a simple chiral cinnamylsilane reagent and is characterized by experimental simplicity and extraordinarily high levels of enantioselectivity. Further, a remarkable and unprecedented diastereochemical reversal has been realized whereby either diastereomer may be accessed from the same trans-cinnamylsilane based upon a subtle change to the imine, thus obviating the usual requirement for both the trans- and cis-cinnamylsilanes.

  DOI：

  10.1021/ja076035h

文献信息

• Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch
  作者：John D. Huber、James L. Leighton

  DOI：10.1021/ja076035h

  日期：2007.11.28

  The first general method for the enantioselective cinnamylation of aldimines is reported. The method utilizes a simple chiral cinnamylsilane reagent and is characterized by experimental simplicity and extraordinarily high levels of enantioselectivity. Further, a remarkable and unprecedented diastereochemical reversal has been realized whereby either diastereomer may be accessed from the same trans-cinnamylsilane based upon a subtle change to the imine, thus obviating the usual requirement for both the trans- and cis-cinnamylsilanes.