3-(3,4-dimethoxyphenyl)-8-[(N,N-dimethylamino)methyl]-7-hydroxy-2-methyl-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(3,4-dimethoxyphenyl)-8-[(N,N-dimethylamino)methyl]-7-hydroxy-2-methyl-4H-chromen-4-one
• 英文别名: 3-(3,4-dimethoxyphenyl)-8-[(dimethylammonio)methyl]-2-methyl-4-oxo-4H-chromen-7-olate；3-(3,4-dimethoxyphenyl)-8-[(dimethylazaniumyl)methyl]-2-methyl-4-oxochromen-7-olate
• 化学式: C₂₁H₂₃NO₅
• mdl: MFCD04146691
• 分子量: 369.417
• InChiKey: FKFKLNLGHYSBHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-8-[(N,N-dimethylamino)methyl]-7-hydroxy-2-methyl-4H-chromen-4-one 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  New Heterocyclic Pyrano[2',3':5,6]Chromeno[3,2-c]Pyridin-4-Ones 和 Furo[2',3':5,6]Chromeno[3,2-c]Pyridin- 3(2H)-Ones 通过 Hetero-Diels-Alder 反应合成

  摘要：

  研究了类黄酮曼尼希碱在逆电子需求异质 Diels-Alder 反应中的行为。以异黄酮和金酮为例，表明它们的曼尼希碱与 4-(1-甲基-1,2,3,6-四氢吡啶-4-基)吗啉通过消除机制和随后的环加成反应形成新的衍生物杂环系统 pyrano[2',3':5,6]chromeno[3,2-c]pyridin-4-one 和 furo[2',3':5,6]chromeno[3,2-c]pyridin- 3(2H)-一。

  DOI：

  10.1007/s10600-016-1846-6
• 作为产物：
  描述：

  3-(3,4-二甲氧基苯基)-7-羟基-2-甲基-4H-苯并吡喃-4-酮 、 四甲基甲烷二胺 以 异丙醇 为溶剂， 生成 3-(3,4-dimethoxyphenyl)-8-[(N,N-dimethylamino)methyl]-7-hydroxy-2-methyl-4H-chromen-4-one
  参考文献：
  名称：

  Reactivity of Condensed Isoflavone Derivatives for Hydrazine

  摘要：

  研究了从天然异黄酮及其类似物衍生得到的呋喃并[3,2-b]吡喃并[2,3-f]色烯-4-酮、二吡喃并[2,3-b:2,3-f]色烯-4-酮和吡喃并[2,3-a]咕吨-4-酮的肼解重排反应。反应显示以色烯环选择性开环进行。合成了含有呋喃并[3,2-b]色烯-5-醇、吡喃并[2,3-b]色烯-6-醇和咕吨-8-醇片段的多种取代4-芳基吡唑。

  DOI：

  10.1007/s10600-018-2439-3

文献信息

• [EN] 3-ARYL-4H-CHROMENE-4-ONES AS ANTINEOPLASTIC AGENTS FOR THE TREATMENT OF CANCER<br/>[FR] 3-ARYL-4H-CHROMÈNE-4-ONES SERVANT D'AGENTS ANTINÉOPLASIQUES POUR LE TRAITEMENT DU CANCER
  申请人：UNIV KENTUCKY RES FOUND

  公开号：WO2016183157A1

  公开（公告）日：2016-11-17

  Isoflavonoids or pharmaceutically acceptable salts thereof or pharmaceutically acceptable compositions thereof for the treatment of prostate cancer or for the treatment or inhibition of prostate cancer metastasis in a patient in need thereof are disclosed.

  揭示了用于治疗前列腺癌或治疗或抑制患有前列腺癌转移的患者的异黄酮类化合物或其药用可接受盐或药用可接受组合物。
• 3-ARYL-4H-CHROMENE-4-ONES AS ANTINEOPLASTIC AGENTS FOR THE TREATMENT OF CANCER
  申请人：The University of Kentucky Research Foundation

  公开号：US20160332981A1

  公开（公告）日：2016-11-17

  Isoflavonoids or pharmaceutically acceptable salts thereof or pharmaceutically acceptable compositions thereof for the treatment of prostate cancer or for the treatment or inhibition of prostate cancer metastasis in a patient in need thereof are disclosed.
• US9718799B2
  申请人：——

  公开号：US9718799B2

  公开（公告）日：2017-08-01
• New Heterocyclic Pyrano[2′,3′:5,6]Chromeno[3,2-c]Pyridin-4-Ones and Furo[2′,3′:5,6]Chromeno[3,2-c]Pyridin-3(2H)-Ones Synthesized Via a Hetero-Diels–Alder Reaction
  作者：A. V. Popova、G. P. Mrug、K. M. Kondratyuk、S. P. Bondarenko、M. S. Frasinyuk

  DOI：10.1007/s10600-016-1846-6

  日期：2016.11

  hetero-Diels–Alder reactions was studied. Isoflavones and aurones were used as examples to show that their Mannich bases reacted with 4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)morpholine through an elimination mechanism and subsequent cycloaddition to form derivatives of the new heterocyclic systems pyrano[2′,3′:5,6]chromeno[3,2-c]pyridin-4-one and furo[2′,3′:5,6]chromeno[3,2-c]pyridin-3(2H)-one.

  研究了类黄酮曼尼希碱在逆电子需求异质 Diels-Alder 反应中的行为。以异黄酮和金酮为例，表明它们的曼尼希碱与 4-(1-甲基-1,2,3,6-四氢吡啶-4-基)吗啉通过消除机制和随后的环加成反应形成新的衍生物杂环系统 pyrano[2',3':5,6]chromeno[3,2-c]pyridin-4-one 和 furo[2',3':5,6]chromeno[3,2-c]pyridin- 3(2H)-一。
• Reactivity of Condensed Isoflavone Derivatives for Hydrazine
  作者：G. P. Mrug、N. V. Bondarenko、S. P. Bondarenko、M. S. Frasinyuk

  DOI：10.1007/s10600-018-2439-3

  日期：2018.7

  Recyclization by hydrazine of furo[3,2-b]pyrano[2,3-f]chromen-4-ones, dipyrano[2,3-b:2,3-f]chromen4-ones, and pyrano[2,3-a]xanthen-4-ones derived from natural isoflavonoids and their analogs was studied. The reaction was shown to proceed selectively with opening of the chromone ring. Several substituted 4-arylpyrazoles containing furo[3,2-b]chromen-5-ol, pyrano[2,3-b]chromen-6-ol, and xanthen-8-ol fragments were synthesized.

  研究了从天然异黄酮及其类似物衍生得到的呋喃并[3,2-b]吡喃并[2,3-f]色烯-4-酮、二吡喃并[2,3-b:2,3-f]色烯-4-酮和吡喃并[2,3-a]咕吨-4-酮的肼解重排反应。反应显示以色烯环选择性开环进行。合成了含有呋喃并[3,2-b]色烯-5-醇、吡喃并[2,3-b]色烯-6-醇和咕吨-8-醇片段的多种取代4-芳基吡唑。