protosinomenine | 30883-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: protosinomenine
• 英文别名: (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-6-ol
• CAS: 30883-59-1
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: HZRFPHXHCRIHFX-HNNXBMFYSA-N

物化性质

• 沸点：
  504.9±50.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  protosinomenine 在 berberine bridge enzyme 、 氧气 作用下， 生成 (-)-discretamine 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  The berberine bridge forming enzyme in tetrahydroprotoberberine biosynthesis

  摘要：

  DOI：

  10.1016/s0040-4039(01)80070-8
• 作为产物：
  描述：

  聚合甲醛 、 (+-)-Norprotosinomenin 在 sodium acetate 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 protosinomenine 、 1-(3-hydroxy-4-methoxybenzyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol
  参考文献：
  名称：

  Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

  摘要：

  A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethyl-amines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

  DOI：

  10.1021/acs.joc.5b00509

文献信息

• The berberine bridge forming enzyme in tetrahydroprotoberberine biosynthesis
  作者：P. Steffens、N. Nagakura、M.H. Zenk

  DOI：10.1016/s0040-4039(01)80070-8

  日期：1984.1
• Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids
  作者：Andrea Ruiz-Olalla、Martien A. Würdemann、Martin J. Wanner、Steen Ingemann、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1021/acs.joc.5b00509

  日期：2015.5.15

  A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethyl-amines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.