(S)-4-benzyl-3-(3-(3,4-dimethoxyphenyl)propionyl)-2-oxazolidinone | 1373333-25-5

• 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: (S)-4-benzyl-3-(3-(3,4-dimethoxyphenyl)propionyl)-2-oxazolidinone
• 英文别名: (S)-4-benzyl-3-(3-(3,4-dimethoxyphenyl)propanoyl)-oxazolidin-2-one；(4S)-4-benzyl-3-[3-(3,4-dimethoxyphenyl)propanoyl]-1,3-oxazolidin-2-one
• CAS: 1373333-25-5
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: RNZYEJXSPRJDKA-KRWDZBQOSA-N

物化性质

• 熔点：
  91.5-92 °C
• 沸点：
  552.5±40.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-(3-(3,4-dimethoxyphenyl)propionyl)-2-oxazolidinone 在 氯化亚砜 、 双氧水 、 碳酸氢钠 、 三氟乙酸 、 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 dichlorormethane 、 二氯甲烷 、 水 为溶剂， 反应 31.0h， 生成 (S)-7,8-dimethoxy-2,4-dimethyl-4,5-dihydro-1H-benzo[c]azepin-3(2H)-one
  参考文献：
  名称：

  Concise Synthesis of 2-Benzazepine Derivatives and Their Biological Activity

  摘要：

  2-Benzazepines, which are potentially good candidates for new drug therapies to treat skin wounds, were readily prepared from substituted cinnamylamide via an intramolecular Friedel Crafts reaction. With few steps and effective reactions, the procedure enables a rapid derivatization of 2-benzazepines. Moreover, optically active 4-substituted-2-benzazepines were prepared from chiral alpha-substituted cinnamylamides, which were readily prepared by asymmetric alpha-alkylation of chiral cinnamyl oxazolidinone amides. We have easily prepared a library of more than 20 derivatives and examined the biological activity of the compounds.

  DOI：

  10.1021/jo300380z
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 (S)-4-benzyl-3-(3-(3,4-dimethoxyphenyl)propionyl)-2-oxazolidinone
  参考文献：
  名称：

  Concise Synthesis of 2-Benzazepine Derivatives and Their Biological Activity

  摘要：

  2-Benzazepines, which are potentially good candidates for new drug therapies to treat skin wounds, were readily prepared from substituted cinnamylamide via an intramolecular Friedel Crafts reaction. With few steps and effective reactions, the procedure enables a rapid derivatization of 2-benzazepines. Moreover, optically active 4-substituted-2-benzazepines were prepared from chiral alpha-substituted cinnamylamides, which were readily prepared by asymmetric alpha-alkylation of chiral cinnamyl oxazolidinone amides. We have easily prepared a library of more than 20 derivatives and examined the biological activity of the compounds.

  DOI：

  10.1021/jo300380z

文献信息

• 一种高效合成具有特定构型的β-苄基丁内酯 的方法
  申请人：辽宁中医药大学

  公开号：CN105175365B

  公开（公告）日：2018-03-06

  本发明公开一种高效合成具有特定构型的β‑苄基丁内酯的方法，其特点是：以苯丙酸或其衍生物为起始原料，与噁唑烷酮类手性辅基缩合，在大位阻有机碱的作用下，卤乙酸酯进攻苯丙酸羰基邻位碳，成功构建特定手性中心后，水解并回收辅基，相应产物通过分子内酯交换反应生成具有特定构型的β‑苄基丁内酯。利用本发明制备的β‑苄基丁内酯可以应用于大量具有潜在药用价值的二苄基型木脂素的化学合成，具有原料廉价易得，步骤短，收率高，光学纯度高的特点。
• 木脂素衍生物、其制备方法及用途
  申请人：中国科学院上海药物研究所

  公开号：CN115215821A

  公开（公告）日：2022-10-21

  本发明公开了一种木脂素衍生物、其制备方法及用途，所述木脂素衍生物结构如式I所示，式中，各取代基的定义如说明书和权利要求书中所述。本发明的木脂素衍生物，能够作为线粒体呼吸链复合物I抑制剂，抑制线粒体的氧化磷酸化作用及ATP的生成，用于预防和/或治疗与线粒体呼吸链复合物I活性或表达升高、或者线粒体氧化磷酸化作用增强相关的疾病。
• Concise Synthesis of 2-Benzazepine Derivatives and Their Biological Activity
  作者：Masahiro So、Tomoko Kotake、Kenji Matsuura、Makoto Inui、Akio Kamimura

  DOI：10.1021/jo300380z

  日期：2012.4.20

  2-Benzazepines, which are potentially good candidates for new drug therapies to treat skin wounds, were readily prepared from substituted cinnamylamide via an intramolecular Friedel Crafts reaction. With few steps and effective reactions, the procedure enables a rapid derivatization of 2-benzazepines. Moreover, optically active 4-substituted-2-benzazepines were prepared from chiral alpha-substituted cinnamylamides, which were readily prepared by asymmetric alpha-alkylation of chiral cinnamyl oxazolidinone amides. We have easily prepared a library of more than 20 derivatives and examined the biological activity of the compounds.