2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-4-one | 56676-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-4-one
• 英文别名: 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-4-one；3-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-1-naphthalenone；2-Acetyl-5,8-dimethoxy-4-tetralone；1,2,3,4-Tetrahydro-5,8-dimethoxy-4-oxo-2-acetylnaphthalene；1,2,3,4-Tetrahydro-5,8-dimethoxy-4-oxo-2acetylnaphthalene；3-acetyl-5,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 56676-83-6
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: RGQPRKPHBRTYTN-UHFFFAOYSA-N

物化性质

• 熔点：
  106-118 °C
• 沸点：
  428.5±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-4-one 在 三氟化硼乙醚 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 2-Acetyl-5-hydroxy-8-methoxy-6-(4-methoxy-3-phthalido)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Rao, A. V. Rama; Chanda, Bhanu; Borate, H. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 6, p. 521 - 523

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲氧基苄溴 在 氢氟酸 、 potassium carbonate 作用下， 以 sodium hydroxide 、 丙酮 为溶剂， 反应 30.0h， 生成 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-4-one
  参考文献：
  名称：

  一种方便的全合成（±）4-demethoxydaunomycinone的方法

  摘要：

  描述了一种从2-甲基氢醌开始合成（±）4-脱甲氧基金牛烯酮的方便且最实用的方法。

  DOI：

  10.1016/0040-4020(82)80060-4

文献信息

• Synthesis and biological activity of novel shikonin analogues
  作者：Wenjing Wang、Mei Dai、Caihua Zhu、Jiangang Zhang、Liping Lin、Jian Ding、Wenhu Duan

  DOI：10.1016/j.bmcl.2008.12.032

  日期：2009.2

  A series of shikonin analogues with side chain variants have been synthesized and evaluated for antitumor activity. These novel analogues show a broad spectrum of in vitro cytotoxicity against various cancer cell lines. Additionally, some analogues were also found to have the ability to decrease the expression level of HIF-1 alpha in breast cancer cells MDA-MB-231 under hypoxia. The features of these analogues suggest their potential in cancer therapy. (C) 2008 Elsevier Ltd. All rights reserved.
• Kudav; Kulkarni; Kochrekar, Journal of the Indian Chemical Society, 2002, vol. 79, # 1, p. 62 - 64
  作者：Kudav、Kulkarni、Kochrekar

  DOI：——

  日期：——
• Facile Total Syntheses of Idarubicinone‐7‐β‐<scp>D</scp>‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives
  作者：Young S. Rho、Jihyung Park、Gyuil Kim、Hyesun Kim、Hongsig Sin、Pyoung Won Suh、Dong Jin Yoo

  DOI：10.1081/scc-120030758

  日期：2004.12.31

  Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (+/-)-idarubicinone 3b by general methods. Esterification of (+/-)-3b with (S)-(+)-O-acetylmandelic acid with subsequent separation and deprotection gave (+)-3b and (-)-3b. Reaction of separated two stereoisomers with acetobromo-alpha-D-glucuronic acid methyl ester respective followed by hydrolysis using lithium hydroxide and amberite cation exchange resin furnished two kinds of idarubicinone-7-beta-D-glucuronide (20 and 21) that are coupled at C-7 position of idarubicinone.
• Chanda, Bhanu; Borate, H. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1002 - 1007
  作者：Chanda, Bhanu、Borate, H. B.

  DOI：——

  日期：——
• US4697005A
  申请人：——

  公开号：US4697005A

  公开（公告）日：1987-09-29