(S)-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid
• 英文别名: (S)-3-(3,4-dimethoxy-phenyl)-2-methyl-propionic acid；(S)-3-(3,4-Dimethoxy-phenyl)-2-methyl-propionsaeure；[S,(+)]-2-(3,4-Dimethoxybenzyl)propionic acid；(2S)-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: UDWOGKXUYHXPKV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid 在 氯化亚砜 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 dichlorormethane 、 二氯甲烷 为溶剂， 反应 24.0h， 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-(3,4-dimethoxy-phenyl)-propionyl chloride 在 双氧水 、 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 32.0h， 生成 (S)-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid
  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

• The Absolute Configuration of Lignans²
  作者：Anthony W. Schrecker、Jonathan L. Hartwell

  DOI：10.1021/ja01571a055

  日期：1957.7
• Resolution and Rearrangement of α-Methylhydrocinnamic Acid and of Its 3,4-Dimethoxy Derivative
  作者：ANTHONY W. SCHRECKER

  DOI：10.1021/jo01352a006

  日期：1957.1
• TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS
  申请人：Onyx Therapeutics, Inc.

  公开号：US20160368946A1

  公开（公告）日：2016-12-22

  Provided herein are tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of diseases including inflammation and neurodegenerative disease.
• US9434761B2
  申请人：——

  公开号：US9434761B2

  公开（公告）日：2016-09-06
• 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.