3-(1-苄基-1H-吲哚-3-基)丙酸乙酯 | 850894-93-8

• 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
• 中文名称: 3-(1-苄基-1H-吲哚-3-基)丙酸乙酯
• 英文名称: ethyl 3-(1-benzyl-1H-indol-3-yl)propanoate
• 英文别名: ethyl 3-(1-benzyl-1H-3-indolyl)propanoate；Ethyl 3-(1-benzylindol-3-yl)propanoate
• CAS: 850894-93-8
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: SXHJSMJTLFJLRH-UHFFFAOYSA-N

物化性质

• 沸点：
  473.8±33.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-苄基-1H-吲哚-3-基)丙酸乙酯 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到3-(1-benzyl-1H-indol-3-yl)propanal
  参考文献：
  名称：

  Synthesis of 2-Alkyl-Substituted Chromone Derivatives Using Microwave Irradiation

  摘要：

  A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using diisopropylamine in EtOH at 170 degrees C for 1 h gave moderate to high yields (43-88%). The 4-chromanones could be further converted into highly functionalized 2,3,6,8-tetrasubstituted chromones in which a 3-substituent (acetate, amine, or bromine) was introduced via straightforward chemical transformations.

  DOI：

  10.1021/jo802783z
• 作为产物：
  描述：

  3-吲哚丙酸 在 盐酸 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 3-(1-苄基-1H-吲哚-3-基)丙酸乙酯
  参考文献：
  名称：

  New N-pyridinyl(methyl)-indolalkanamides acting as topical inflammation inhibitors

  摘要：

  The authors have described the synthetic way to new N-pyridinyl(methyl)indolylpropanamides acting as non acidic NSAIDs. Pharmacomodulation was carried out at N-1 and C-5 of the indole ring and at the level of the propanamide chain. N-(pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propanamide 32 represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.07.057

文献信息

• Synthetic N-pyridinyl(methyl)-indol-3-ylpropanamides as new potential immunosuppressive agents
  作者：Delphine Carbonnelle、Morgane Lardic、Alexandra Dassonville、Elise Verron、Jean-Yves Petit、Muriel Duflos、François Lang

  DOI：10.1016/j.ejmech.2006.12.013

  日期：2007.5

  Several N-pyridinyl(methyl)-indol-3-ylpropanamides were synthesized and pharmacological evaluations of their immumosuppressive potential were performed. Among thirteen compounds tested in vitro on murine T proliferation, three showed interesting inhibiting activity. For the most active compound (propanamide 18), immunosuppressive activity was documented both in vitro on human T lymphocytes proliferation and in vivo on mice delayed-type hypersensitivity. These experimental data demonstrated that these compounds hold potential as immunosuppressive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Poly(ethylene Glycol) (400) as Superior Solvent Medium against Ionic Liquids for Catalytic Hydrogenations with PtO₂
  作者：Srivari Chandrasekhar、Samala Jaya Prakash、Chennamaneni Lohitha Rao

  DOI：10.1021/jo052604x

  日期：2006.3.1

  Adams' catalyst in poly(ethylene glycol) (PEG) (400) has been found to be a superior solvent over the ionic liquids by severalfold in promoting the hydrogenation of various functional groups. Both the catalyst and PEG were recycled efficiently over 10 runs without loss of activity, and substrate cross contamination was not observed despite a change in the substrate four times.
• CN116478083
  申请人：——

  公开号：——

  公开（公告）日：——
• New N-pyridinyl(methyl)-indolalkanamides acting as topical inflammation inhibitors
  作者：Alexandra Dassonville、Anne Bretéché、Johan Evano、Muriel Duflos、Guillaume le Baut、Nicole Grimaud、Jean-Yves Petit

  DOI：10.1016/j.bmcl.2004.07.057

  日期：2004.11

  The authors have described the synthetic way to new N-pyridinyl(methyl)indolylpropanamides acting as non acidic NSAIDs. Pharmacomodulation was carried out at N-1 and C-5 of the indole ring and at the level of the propanamide chain. N-(pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propanamide 32 represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. (C) 2004 Published by Elsevier Ltd.
• Synthesis of 2-Alkyl-Substituted Chromone Derivatives Using Microwave Irradiation
  作者：Maria Fridén-Saxin、Nils Pemberton、Krystle da Silva Andersson、Christine Dyrager、Annika Friberg、Morten Grøtli、Kristina Luthman

  DOI：10.1021/jo802783z

  日期：2009.4.3

  A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using diisopropylamine in EtOH at 170 degrees C for 1 h gave moderate to high yields (43-88%). The 4-chromanones could be further converted into highly functionalized 2,3,6,8-tetrasubstituted chromones in which a 3-substituent (acetate, amine, or bromine) was introduced via straightforward chemical transformations.