N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-methoxy-3-phenylmethoxyphenyl)-N-[(1S)-1-phenylethyl]acetamide | 1206614-01-8

• 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: N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-methoxy-3-phenylmethoxyphenyl)-N-[(1S)-1-phenylethyl]acetamide
• CAS: 1206614-01-8
• 化学式: C₃₄H₃₇NO₅
• 分子量: 539.671
• InChiKey: PIOGORHFCMUFCZ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-methoxy-3-phenylmethoxyphenyl)-N-[(1S)-1-phenylethyl]acetamide 在 三氯氧磷 、 sodium tetrahydroborate 作用下， 以 苯 、 甲醇 为溶剂， 以89%的产率得到(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-[[4-methoxy-3-(phenylmethoxy)phenyl]methyl]-2-[(1S)-1-phenylethyl]isoquinoline
  参考文献：
  名称：

  Enantioselective Total Synthesis and X-ray Structures of the Tetrahydroprotoberberine Alkaloids (−)-(S)-Tetrahydropalmatrubine and (−)-(S)-Corytenchine

  摘要：

  Enantioselective total syntheses and X-ray structures of both (S)-tetrahydropalmatrubine (2) and (S)-corytenchine (3) are reported for the first time. They were both derived from (S)-N-norlaudanidine, a benzyltetrahydroisoquinoline that was synthesized with high (>95% ee) enantioselectivity using a chiral auxiliary-assisted Bischler-Napieralski cyclization/reduction approach.

  DOI：

  10.1021/np1001169
• 作为产物：
  描述：

  (S)-(-)-[2-(3,4-二甲氧基苯基)乙基](1-苯基乙基)胺 、 2-(3-(苄氧基)-4-甲氧基苯基)乙酰氯 在 水 、 sodium hydroxide 作用下， 反应 1.0h， 以72%的产率得到N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-methoxy-3-phenylmethoxyphenyl)-N-[(1S)-1-phenylethyl]acetamide
  参考文献：
  名称：

  （S）-和（R）-N-去甲罗丹定的对映选择性合成和X射线结构：微量鸦片成分

  摘要：

  描述了N-去甲罗丹定的一种对映体的选择性合成，N-去甲罗丹宁是一种次要的罂粟罂粟苄基四氢异喹啉生物碱。这是通过使用手性辅助介导的Bischler-Napieralski环化-硼氢化钠还原策略来实现的。报告了这些仲胺各自的X射线晶体结构。

  DOI：

  10.1016/j.tetlet.2009.10.114

文献信息

• Enantioselective syntheses and X-ray structures of (S)- and (R)-N-norlaudanidine: trace opium constituents
  作者：Ahmed L. Zein、Otman O. Dakhil、Louise N. Dawe、Paris E. Georghiou

  DOI：10.1016/j.tetlet.2009.10.114

  日期：2010.1

  The enantioselective synthesis of each of the enantiomers of N-norlaudanidine, a minor Papaver somniferum opium benzyltetrahydoisoquinoline alkaloid is described. This was achieved using a chiral auxiliary-mediated Bischler–Napieralski cyclization-sodium borohydride reduction strategy. The X-ray crystal structures of each of these secondary amines are reported.

  描述了N-去甲罗丹定的一种对映体的选择性合成，N-去甲罗丹宁是一种次要的罂粟罂粟苄基四氢异喹啉生物碱。这是通过使用手性辅助介导的Bischler-Napieralski环化-硼氢化钠还原策略来实现的。报告了这些仲胺各自的X射线晶体结构。
• Enantioselective Total Synthesis and X-ray Structures of the Tetrahydroprotoberberine Alkaloids (−)-(<i>S</i>)-Tetrahydropalmatrubine and (−)-(<i>S</i>)-Corytenchine
  作者：Ahmed L. Zein、Louise N. Dawe、Paris E. Georghiou

  DOI：10.1021/np1001169

  日期：2010.8.27

  Enantioselective total syntheses and X-ray structures of both (S)-tetrahydropalmatrubine (2) and (S)-corytenchine (3) are reported for the first time. They were both derived from (S)-N-norlaudanidine, a benzyltetrahydroisoquinoline that was synthesized with high (>95% ee) enantioselectivity using a chiral auxiliary-assisted Bischler-Napieralski cyclization/reduction approach.