methyl 3-(m-methoxyphenyl)-2-methylpropionate | 62007-42-5

• 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: methyl 3-(m-methoxyphenyl)-2-methylpropionate
• 英文别名: methyl 3-(3-methoxyphenyl)-2-methylpropanoate
• CAS: 62007-42-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: YOIMDRWWRMRCBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(m-methoxyphenyl)-2-methylpropionate 在 三甲基氯硅烷 、 sodium 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以50%的产率得到4-Hydroxy-1,6-bis-(3-methoxy-phenyl)-2,5-dimethyl-hexan-3-one
  参考文献：
  名称：

  5,6,11,12-Tetrahydrochrysenes: synthesis of rigid stilbene systems designed to be fluorescent ligands for the estrogen receptor

  摘要：

  We have prepared a series of tetrahydrochrysenes as fluorescent ligands for the estrogen receptor. The stilbene chromophore in this tetracyclic system is held rigid and is adorned with an electron-donating hydroxyl group at C-8 that corresponds to the phenolic hydroxyl of estrogens and an electron acceptor at C-2 to give a donor-acceptor fluorophore. Additional substituents at C-5 and C-11 provide additional bulk that improves receptor binding affinity without distorting the planar conjugated system. The tetrahydrochrysene core was prepared by an acyloin condensation of alpha-alkyl m-methoxyhydrocinnamate esters, followed by a double dehydrative cyclization. The cis and trans isomers of the alkyl substituted systems could be separated and their stereochemistry ascertained by X-ray crystallographic analysis; the trans isomer has the higher receptor binding affinity, and the derivative with ethyl substituents at C-5 and C-11 has the best affinity. The donor-acceptor systems were prepared by functional group manipulations on one of the aromatic methoxy groups: conversion to the trifluoromethanesulfonate was followed by a palladium-mediated carbonylation to give the acetyl derivative and methoxycarbonylation to give the ester. The ester was further elaborated to the amide and nitrile. The nitro compound was prepared by nitration of protio system, itself prepared by hydrogenolysis of the trifluoromethanesulfonate. As will be described later, these tetrahydrochrysenes provide a favorable combination of estrogen receptor binding affinity and long wavelength, high quantum yield fluorescence to make them useful as fluorescent ligands for the estrogen receptor.

  DOI：

  10.1021/jo00030a039
• 作为产物：
  描述：

  3-Methoxycinnamic acid 在 palladium hydroxide - carbon N,N-二甲基丙烯基脲 、 硫酸 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -78.0~80.0 ℃ 、101.33 kPa 条件下， 反应 48.25h， 生成 methyl 3-(m-methoxyphenyl)-2-methylpropionate
  参考文献：
  名称：

  5,6,11,12-Tetrahydrochrysenes: synthesis of rigid stilbene systems designed to be fluorescent ligands for the estrogen receptor

  摘要：

  We have prepared a series of tetrahydrochrysenes as fluorescent ligands for the estrogen receptor. The stilbene chromophore in this tetracyclic system is held rigid and is adorned with an electron-donating hydroxyl group at C-8 that corresponds to the phenolic hydroxyl of estrogens and an electron acceptor at C-2 to give a donor-acceptor fluorophore. Additional substituents at C-5 and C-11 provide additional bulk that improves receptor binding affinity without distorting the planar conjugated system. The tetrahydrochrysene core was prepared by an acyloin condensation of alpha-alkyl m-methoxyhydrocinnamate esters, followed by a double dehydrative cyclization. The cis and trans isomers of the alkyl substituted systems could be separated and their stereochemistry ascertained by X-ray crystallographic analysis; the trans isomer has the higher receptor binding affinity, and the derivative with ethyl substituents at C-5 and C-11 has the best affinity. The donor-acceptor systems were prepared by functional group manipulations on one of the aromatic methoxy groups: conversion to the trifluoromethanesulfonate was followed by a palladium-mediated carbonylation to give the acetyl derivative and methoxycarbonylation to give the ester. The ester was further elaborated to the amide and nitrile. The nitro compound was prepared by nitration of protio system, itself prepared by hydrogenolysis of the trifluoromethanesulfonate. As will be described later, these tetrahydrochrysenes provide a favorable combination of estrogen receptor binding affinity and long wavelength, high quantum yield fluorescence to make them useful as fluorescent ligands for the estrogen receptor.

  DOI：

  10.1021/jo00030a039

文献信息

• STYRENYL DERIVATIVE COMPOUNDS FOR TREATING OPHTHALMIC DISEASES AND DISORDERS
  申请人：Scott Ian Leslie

  公开号：US20120129860A1

  公开（公告）日：2012-05-24

  The present invention relates generally to compositions and methods for treating neurodegenerative diseases and disorders, particularly ophthalmic diseases and disorders. Provided herein are styrenyl derivative compounds, including but not limited to stilbene derivative compounds, and compositions comprising these compounds, that are useful for treating and preventing ophthalmic diseases and disorders, including age-related macular degeneration (AMD) and Stargardt's Disease.

  本发明通常涉及用于治疗神经退行性疾病和障碍的组合物和方法，特别是用于治疗眼科疾病和障碍。本文提供了包括但不限于苯乙烯衍生物化合物和含有这些化合物的组合物，这些化合物对于治疗和预防眼科疾病和障碍，包括年龄相关性黄斑退化（AMD）和Stargardt病都非常有用。
• Styrenyl Derivative Compounds for Treating Ophthalmic Diseases and Disorders
  申请人：Acucela Inc.

  公开号：US20150166494A1

  公开（公告）日：2015-06-18

  The present invention relates generally to compositions and methods for treating neurodegenerative diseases and disorders, particularly ophthalmic diseases and disorders. Provided herein are styrenyl derivative compounds, including but not limited to stilbene derivative compounds, and compositions comprising these compounds, that are useful for treating and preventing ophthalmic diseases and disorders, including age-related macular degeneration (AMD) and Stargardt's Disease.

  本发明涉及一般用于治疗神经退行性疾病和紊乱的组合物和方法，特别是用于治疗眼科疾病和紊乱。本文提供了包括但不限于苯乙烯衍生物化合物和含有这些化合物的组合物，这些化合物可用于治疗和预防眼科疾病和紊乱，包括老年性黄斑变性（AMD）和Stargardt病。
• ANTIDIABETIC COMPOUNDS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3102198B1

  公开（公告）日：2020-08-26
• US8420863B2
  申请人：——

  公开号：US8420863B2

  公开（公告）日：2013-04-16
• US8653142B2
  申请人：——

  公开号：US8653142B2

  公开（公告）日：2014-02-18