N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-methoxyphenyl)ethylamine | 1620818-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-methoxyphenyl)ethylamine
• 英文别名: 2-Methoxy-5-[2-[(2-nitrophenyl)sulfanylamino]ethyl]phenol；2-methoxy-5-[2-[(2-nitrophenyl)sulfanylamino]ethyl]phenol
• CAS: 1620818-54-3
• 化学式: C₁₅H₁₆N₂O₄S
• 分子量: 320.369
• InChiKey: JSBPUGJKVIIEPX-UHFFFAOYSA-N

物化性质

• 沸点：
  513.9±60.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-methoxyphenyl)ethylamine 在 盐酸 、 1,1’-bi-2-naphthol 、 (R)-3,3′-bis(2,4,6-triisopropylphenyl)-BINOL-phosphoric acid 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 1.42h， 生成 (R)-7-methoxy-1-(4-methoxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-6-ol
  参考文献：
  名称：

  Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines

  摘要：

  A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.

  DOI：

  10.1021/jo501099h
• 作为产物：
  描述：

  2-(3-(苄氧基)-4-甲氧基苯基)乙胺 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 19.08h， 生成 N-(2-nitrophenylsulfenyl)-β-(3-hydroxy-4-methoxyphenyl)ethylamine
  参考文献：
  名称：

  Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines

  摘要：

  A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.

  DOI：

  10.1021/jo501099h

文献信息

• Consecutive Pictet-Spengler Condensations toward Bioactive 8-Benzylprotoberberines: Highly Selective Total Syntheses of (+)-Javaberine A, (+)-Javaberine B, and (-)-Latifolian A
  作者：Jenifer Kayhan、Martin J. Wanner、Steen Ingemann、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1002/ejoc.201600764

  日期：2016.8

  solvent: 99: 1 para selectivity was obtained in trifluoroethanol leading to (+)javaberine A; 81: 19 ortho selectivity was reached in apolar aprotic solvents for the synthesis of (+)-javaberine B. Complete, natural diastereoselectivity was observed in the second PS. Through selective catechol oxidation the spirocyclic alkaloid (-)-latifolian A was prepared from protected (+)-javaberine A.

  Enantiopure 8-苄基原小檗碱是通过两个连续的 Pictet-Spengler (PS) 缩合与受保护的 3,4-二羟基苯乙醛合成的。(+)-(R)-去甲原青藤碱的第一个 PS 用 5 mol-% 的 (R)-TRIP 作为手性布朗斯台德酸优化至 90% ee（研磨后 > 99% ee）。第二个 PS 不需要任何催化剂，其区域选择性强烈依赖于溶剂：在三氟乙醇中获得 99:1 的对位选择性，生成 (+)javaberine A；81: 19 在非质子惰性溶剂中达到了合成 (+)-javaberine B 的邻位选择性。在第二个 PS 中观察到完全的天然非对映选择性。通过选择性儿茶酚氧化，从受保护的 (+)-javaberine A 制备了螺环生物碱 (-)-latifolian A。
• 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.
• ANTI-ALS COMPOUNDS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20230037538A1

  公开（公告）日：2023-02-09

  The present invention relates to compounds expected to be useful in the prevention and/or treatment of diseases such as amyotrophic lateral sclerosis, frontotemporal dementia, chronic traumatic encephalopathy, Alzheimer's disease, frontotemporal lobar degeneration, multisystem proteinopathy and the like, a method for preventing or treating such diseases, and the like.
• Organocatalytic Enantioselective Pictet–Spengler Reactions for the Syntheses of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines
  作者：Elma Mons、Martin J. Wanner、Steen Ingemann、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1021/jo501099h

  日期：2014.8.15

  A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-Spengler reactions. The sulfenamide moiety is crucial for the rate and enantioselectivity of the iminium ion cyclization and the products are readily recrystallized to high enantiomeric purity. Using this methodology we synthesized the natural products (R)-crispine A, (R)-calycotomine and (R)-colchietine, the synthetic drug (R)-almorexant and the (S)-enantiomer of a biologically active (R)-AMPA-antagonist.