1-[2,4-二羟基-3-碘-6-(甲氧基甲氧基)苯基]乙酮 | 321569-79-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[2,4-二羟基-3-碘-6-(甲氧基甲氧基)苯基]乙酮
• 英文名称: 2',4'-dihydroxy-3'-iodo-6'-methoxymethoxyacetophenone
• 英文别名: Ethanone, 1-[2,4-dihydroxy-3-iodo-6-(methoxymethoxy)phenyl]-；1-[2,4-dihydroxy-3-iodo-6-(methoxymethoxy)phenyl]ethanone
• CAS: 321569-79-3
• 化学式: C₁₀H₁₁IO₅
• 分子量: 338.099
• InChiKey: QQKGPNKPQSGWKX-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  378.8±42.0 °C(Predicted)
• 密度：
  1.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[2,4-二羟基-3-碘-6-(甲氧基甲氧基)苯基]乙酮 在 盐酸 、 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.75h， 生成 2,4,2',4'-tetrakis(benzyloxy)-6'-benzoyloxy-3'-iodochalcone
  参考文献：
  名称：

  Regioselective Synthesis of 6-Alkyl- and 6-Prenylpolyhydroxyisoflavones and 6-Alkylcoumaronochromone Derivatives

  摘要：

  钯催化的6-碘异黄酮与2-甲基-3-丁炔-2-醇的耦合反应，从3′-碘乙酰苯衍生物制备，生成6-炔基异黄酮衍生物，经过氢化得到6-烷基羟基异黄酮（桑酮水合物）（2）。2的脱水反应生成2′,4′,5,7-四羟基-6-异戊烯基异黄酮（桑酮）（1）。白桑酮水合物（3）也通过类似方法从6-碘三苄氧基异黄酮合成。6-烷基-4′,5,7-三羟基香豆素并色酮（4）通过2与邻氯苯醌的氧化环合反应合成。

  DOI：

  10.1248/cpb.52.1285
• 作为产物：
  描述：

  2',4'-bis(benzyloxy)-6'-methoxymethoxyacetophenone 在 palladium on activated charcoal 氢气 、 碘 、 过碘酸 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 1-[2,4-二羟基-3-碘-6-(甲氧基甲氧基)苯基]乙酮
  参考文献：
  名称：

  Regioselective Synthesis of 6-Alkyl- and 6-Prenylpolyhydroxyisoflavones and 6-Alkylcoumaronochromone Derivatives

  摘要：

  钯催化的6-碘异黄酮与2-甲基-3-丁炔-2-醇的耦合反应，从3′-碘乙酰苯衍生物制备，生成6-炔基异黄酮衍生物，经过氢化得到6-烷基羟基异黄酮（桑酮水合物）（2）。2的脱水反应生成2′,4′,5,7-四羟基-6-异戊烯基异黄酮（桑酮）（1）。白桑酮水合物（3）也通过类似方法从6-碘三苄氧基异黄酮合成。6-烷基-4′,5,7-三羟基香豆素并色酮（4）通过2与邻氯苯醌的氧化环合反应合成。

  DOI：

  10.1248/cpb.52.1285

文献信息

• Regioselective Synthesis of Prenylisoflavones: Syntheses of Luteone and Luteone Hydrate
  作者：Masao Tsukayama、Hironari Wada、Masashi Kishida、Masaki Nishiuchi、Yasuhiko Kawamura

  DOI：10.1246/cl.2000.1362

  日期：2000.12

  The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3′-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave the 6-alkynylisoflavone derivative, which was hydrogenated to give the 6-alkylhydroxyisoflavone (luteone hydrate) 2. Dehydration of 2 gave 2′,4′,5,7-tetrahydroxy-6-prenylisoflavone (luteone).

  由 3′-碘苯乙酮衍生物制备的 6-碘异黄酮与 2-甲基-3-丁炔-2-醇在钯催化下发生偶联反应，得到 6-烷基异黄酮衍生物，该衍生物经氢化后得到 6-烷基羟基异黄酮（木犀草素水合物）2。2 脱水后得到 2′,4′,5,7-四羟基-6-异戊烯基异黄酮（木犀草素）。
• Microwave-assisted regioselective synthesis of natural 6-prenylpolyhydroxyisoflavones and their hydrates with hypervalent iodine reagents
  作者：Mohammad M. Hossain、Yasuhiko Kawamura、Kazuyo Yamashita、Masao Tsukayama

  DOI：10.1016/j.tet.2006.06.066

  日期：2006.9

  Microwave-assisted oxidative rearrangement of 3'-iodotetraalkoxychalcones with hypervalent iodine such as [hydroxy(tosyloxy)iodo]benzene or [bis(trifluoroacetoxy)iodo] benzene, followed by microwave-mediated hydrolysis and in situ cyclization of the resultant acetals gave 6-iodotrialkoxyisoflavones. Pd(0)-catalyzed coupling reaction of the 6-iodoisoflavones with 2-methyl-3-butyn-2-of under microwave irradiation gave 6-alkynylisoflavones, whose hydrogenation gave the respective hydrates of wighteone, lupisoflavone and derrubone. Wighteone (1a), lupisoflavone (1b) and derrubone (1c) were obtained by dehydration of their respective hydrates under microwave irradiation. (c) 2006 Elsevier Ltd. All rights reserved.
• Regioselective Synthesis of 6‐Prenylpolyhydroxyisoflavone (Wighteone) and Wighteone Hydrate with Hypervalent Iodine
  作者：Takanori Tokuoka、Kazuyo Yamashita、Yasuhiko Kawamura、Masao Tsukayama、Mohammad M. Hossain

  DOI：10.1080/00397910500514121

  日期：2006.5

  The oxidative rearrangement of 3'-iodotetraalkoxychalcone with [hydroxyl(tosyloxy)iodo]benzene, followed by cyclization of the resultant acetal gave 6-iodotrialkoxyisoflavone. The coupling reaction of the isoflavone with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone, whose hydrogenation gave wighteone hydrate. Wighteone was synthesized by dehydration of wighteone hydrate.
• Regioselective Synthesis of 6-Alkyl- and 6-Prenylpolyhydroxyisoflavones and 6-Alkylcoumaronochromone Derivatives
  作者：Masao Tsukayama、Hironari Wada、Yasuhiko Kawamura、Kazuyo Yamashita、Masaki Nishiuchi

  DOI：10.1248/cpb.52.1285

  日期：——

  The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3′-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone derivative, which was hydrogenated to give 6-alkylhydroxyisoflavone (luteone hydrate) (2). Dehydration of 2 gave 2′,4′,5,7-tetrahydroxy-6-prenylisoflavone (luteone) (1). Wighteone hydrate (3) was also synthesized from 6-iodotris(benzyloxy)isoflavone in a similar manner. 6-Alkyl-4′5,7-trihydroxy-coumaronochromone (4) was synthesized by oxidative cyclization of 2 with o-chloranil.

  钯催化的6-碘异黄酮与2-甲基-3-丁炔-2-醇的耦合反应，从3′-碘乙酰苯衍生物制备，生成6-炔基异黄酮衍生物，经过氢化得到6-烷基羟基异黄酮（桑酮水合物）（2）。2的脱水反应生成2′,4′,5,7-四羟基-6-异戊烯基异黄酮（桑酮）（1）。白桑酮水合物（3）也通过类似方法从6-碘三苄氧基异黄酮合成。6-烷基-4′,5,7-三羟基香豆素并色酮（4）通过2与邻氯苯醌的氧化环合反应合成。