1-benzyl-3-(dimethylanoethyl)-5-methoxyindole | 330851-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-benzyl-3-(dimethylanoethyl)-5-methoxyindole
• 英文别名: 2-(1-benzyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethylamine；1-Benzyl-5-methoxy-3-(β-dimethylamino-ethyl)-indol；MES 9191；[2-(1-benzyl-5-methoxy-indol-3-yl)-ethyl]-dimethyl-amine；[2-(1-Benzyl-5-methoxy-1H-indol-3-yl)-ethyl]-dimethyl-amine；2-(1-benzyl-5-methoxyindol-3-yl)-N,N-dimethylethanamine
• CAS: 330851-38-2
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: LTGLAVOFBOVUDU-UHFFFAOYSA-N

物化性质

• 沸点：
  476.4±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(dimethylanoethyl)-5-methoxyindole 在 sodium 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 为溶剂， 反应 1.5h， 生成 蟾毒色胺
  参考文献：
  名称：

  Aromatization of 1,6,7,7a-Tetrahydro-2H-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1H-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin

  摘要：

  Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

  DOI：

  10.1021/jo0110597
• 作为产物：
  描述：

  1-苄基-5-甲氧基-1H-吲哚-3-乙酸甲酯 在 lithium aluminium tetrahydride 、 氰化钠 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 144.0h， 生成 1-benzyl-3-(dimethylanoethyl)-5-methoxyindole
  参考文献：
  名称：

  Aromatization of 1,6,7,7a-Tetrahydro-2H-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1H-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin

  摘要：

  Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

  DOI：

  10.1021/jo0110597

文献信息

• Agents useful for reducing amyloid precursor protein and treating demantia and methods of use thereof
  申请人：——

  公开号：US20040138282A1

  公开（公告）日：2004-07-15

  The present invention provides compounds and methods of administering compounds to a subject taht can reduce &bgr;APP production and that is not toxic in a wide range of dosages. The present invention also provides non-carbamate compounds and methods of administering such compounds to a subject that can reduce &bgr;APP production and that is not tocix in a wide range of dosages. It has been discovered that either the racemic or enantiomerically pure non-carbamate compounds can be used to decrease &bgr;APP production.

  本发明提供了化合物和给予这些化合物给受试者的方法，可以减少βAPP的产生，并且在广泛剂量范围内不具有毒性。本发明还提供了非碳酸酯化合物和给予这些化合物给受试者的方法，可以减少βAPP的产生，并且在广泛剂量范围内不具有毒性。已经发现无论是混合物还是对映纯的非碳酸酯化合物都可以用于降低βAPP的产生。
• Lee; Rangisetty; Dukat, Medicinal Chemistry Research, 2000, vol. 10, # 4, p. 230 - 242
  作者：Lee、Rangisetty、Dukat、Slassi、Maclean、Lee、Glennon

  DOI：——

  日期：——
• AGENTS USEFUL FOR REDUCING AMYLOID PRECURSOR PROTEIN AND TREATING DEMANTIA AND METHODS OF USE THEREOF
  申请人：GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1349858B1

  公开（公告）日：2008-08-27
• Agents useful for reducing amylioid precursor protein and treating dementia and methods of use thereof
  申请人：Greig H. Nigel

  公开号：US20060270729A1

  公开（公告）日：2006-11-30

  The present invention provides compounds and methods of administering compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. The present invention also provides non-carbamate compounds and methods of administering such compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. It has been discovered that either the racemic or enantiomerically pure non-carbamate compounds can be used to decrease βAPP production.
• Agents Useful for Reducing Amyloid Precursor Protein and Treating Dementia and Methods of Use Thereof
  申请人：Greig Nigel H.

  公开号：US20090131501A1

  公开（公告）日：2009-05-21

  The present invention provides compounds and methods of administering compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. The present invention also provides non-carbamate compounds and methods of administering such compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. It has been discovered that either the racemic or enantiomerically pure non-carbamate compounds can be used to decrease βAPP production.