4,7-dimethoxy-5-methyl-6-(3-methylbut-3-en-1-ynyl)benzo[d][1,3]dioxole | 1384513-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4,7-dimethoxy-5-methyl-6-(3-methylbut-3-en-1-ynyl)benzo[d][1,3]dioxole
• 英文别名: antrocamphin O；1,2-methylenedioxy-3,6-bismethoxy-4-(3-methyl-but-3-en-1-ynyl)-5-methylbenzene；4,7-dimethoxy-5-(3-methylbut-3-en-1-ynyl)-6-methyl-1,3-benzodioxole；4,7-dimethoxy-5-methyl-6-(3-methylbut-3-en-1-ynyl)-1,3-benzodioxole
• CAS: 1384513-80-7
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: PEWAHWLMFHMALZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 aluminum (III) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 4,7-dimethoxy-5-methyl-6-(3-methylbut-3-en-1-ynyl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata

  摘要：

  从台湾乳菇（Antrodia camphorata，台湾真菌)的子实体中分离得到一种新的烯炔基苯并二氧戊环类化合物antroca mphin O（1，4，7-二甲氧基-5-甲基-6-（3'-甲基丁-3-烯炔基）苯并[d][1，3]二氧戊环）和已知的苯并二氧戊环类化合物antrocamphinA 和 7-二甲氧基-5-甲基-1，3-苯并二氧戊环。通过光谱数据（包括一维和二维核磁共振波谱、高分辨质谱、红外和紫外光谱）分析和全合成明确指认了antrocamphin O的结构。化合物1的关键步骤是通过Sonogashira反应制备，即以5-碘-4，7-二甲氧基-6-甲基苯和2-甲基丁-1-烯-3-炔作为原料。本研究所分离的苯并二氧戊环类化合物被用于检测其对人结肠癌HT29、HTC15、DLD-1、和COLO 205细胞株的细胞毒活性，并报道了其活性。

  DOI：

  10.3390/molecules18077600

文献信息

• Compound Extracted From Antrodia Cinnamomea and Pharmaceutical composition comprising the same
  申请人：Lee Ching-Kuo

  公开号：US20120029069A1

  公开（公告）日：2012-02-02

  This invention relates to a novel compound extracted from antrodia Cinnamomea and related compounds of formula (1), and pharmaceutical compositions comprising the compound of formula (1) and a pharmaceutically acceptable carrier or excipient. The invention further comprises the method of inhibit cancer cells by administering an effective amount of the compound of formula (1).
• BENZENOID COMPOUNDS OF ANTRODIA CINNAMOMEA, PREPARATION AND ANALYSIS METHOD THEREOF
  申请人：WU YANG-CHANG

  公开号：US20120178945A1

  公开（公告）日：2012-07-12

  Disclosed are a method for preparing an n-hexane extract of the fruiting body of Antrodia cinnamomea (AC), wherein the fruiting body of AC is sequentially extracted with the ethanol solution and the n-hexane solution to obtain the n-hexane extract containing at least one benzenoid compound. The amounts of 4,7-dimethoxy-5-(3-methylbut-3-en-1-ynyl)-6-methyl-1,3-benzodioxole, 4,7-dimethoxy-5-methyl-1,3-benzodioxole, antrocamphine A and the combination thereof in the at least one benzenoid compound are determined using chromatography, NMR and HPLC. In addition, the present invention is applicable on detecting the amounts of benzenoid compounds in the AC healthcare food/drug or the fruiting body of AC, and thus owns the industrial values.
• US8716499B2
  申请人：——

  公开号：US8716499B2

  公开（公告）日：2014-05-06
• US8759549B2
  申请人：——

  公开号：US8759549B2

  公开（公告）日：2014-06-24
• Isolation and Synthesis of a Bioactive Benzenoid Derivative from the Fruiting Bodies of Antrodia camphorata
  作者：Pi-Yu Chen、Jen-Der Wu、Kai-Yih Tang、Chieh-Chou Yu、Yueh-Hsiung Kuo、Wen-Bin Zhong、Ching-Kuo Lee

  DOI：10.3390/molecules18077600

  日期：——

  A new enynyl-benzenoid, antrocamphin O (1,4,7-dimethoxy-5-methyl-6-(3′-methylbut-3-en-1-ynyl)benzo[d][1,3]dioxide), and the known benzenoids antrocamphin A and 7-dimethoxy-5-methyl-1,3-benzodioxole, were isolated from the fruiting bodies of Antrodia camphorata (Taiwanofungus camphoratus). The structure of antrocamphin O was unambiguously assigned by the analysis of spectral data (including 1D and 2D NMR, high-resolution MS, IR, and UV) and total synthesis. Compound 1 was prepared through the Sonogashira reaction of 5-iodo-4,7-dimethoxy-6-methylbenzene and 2-methylbut-1-en-3-yne as the key step. The benzenoids were tested for cytotoxicity against the HT29, HTC15, DLD-1, and COLO 205 colon cancer cell lines, and activities are reported herein.

  从台湾乳菇（Antrodia camphorata，台湾真菌)的子实体中分离得到一种新的烯炔基苯并二氧戊环类化合物antroca mphin O（1，4，7-二甲氧基-5-甲基-6-（3'-甲基丁-3-烯炔基）苯并[d][1，3]二氧戊环）和已知的苯并二氧戊环类化合物antrocamphinA 和 7-二甲氧基-5-甲基-1，3-苯并二氧戊环。通过光谱数据（包括一维和二维核磁共振波谱、高分辨质谱、红外和紫外光谱）分析和全合成明确指认了antrocamphin O的结构。化合物1的关键步骤是通过Sonogashira反应制备，即以5-碘-4，7-二甲氧基-6-甲基苯和2-甲基丁-1-烯-3-炔作为原料。本研究所分离的苯并二氧戊环类化合物被用于检测其对人结肠癌HT29、HTC15、DLD-1、和COLO 205细胞株的细胞毒活性，并报道了其活性。