2',4'-bis(benzyloxy)-6'-methoxymethoxyacetophenone | 67052-53-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',4'-bis(benzyloxy)-6'-methoxymethoxyacetophenone
• 英文别名: Ethanone, 1-[2-(methoxymethoxy)-4,6-bis(phenylmethoxy)phenyl]-；1-[2-(methoxymethoxy)-4,6-bis(phenylmethoxy)phenyl]ethanone
• CAS: 67052-53-3
• 化学式: C₂₄H₂₄O₅
• 分子量: 392.452
• InChiKey: UIBKNSQZXDGRQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2',4'-bis(benzyloxy)-6'-methoxymethoxyacetophenone 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 77.5h， 生成 5,7,3'-trihydroxydihydroquercetin 3-acetate 4'-(methyl ether)
  参考文献：
  名称：

  Potential sweetening agents of plant origin. 13. An intensely sweet dihydroflavonol derivative based on a natural product lead compound

  摘要：

  The dihydroflavonol dihydroquercetin 3-acetate (1) was isolated as a sweet constituent of the young shoots of Tessaria dodoneifolia (Hook. & Arn.) Cabrera (Compositae). Compound 1 and dihydroquercetin 3-acetate 4'-(methyl ether) (2), a novel synthetic analogue of this natural product lead compound, were rated by a taste panel as being 80 and 400 times sweeter than a 2% w/v sucrose solution, respectively. Synthetic dihydroquercetin 4'-(methyl ether) (3) showed a reduced sweetness intensity when compared to 2, while (+)-dihydroquercetin (4) was devoid of sweetness. Dihydroflavonol derivatives 1-3 represent a new class of potentially noncaloric and noncariogenic intense sweeteners.

  DOI：

  10.1021/jm00401a030
• 作为产物：
  描述：

  溴甲苯 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.33h， 生成 2',4'-bis(benzyloxy)-6'-methoxymethoxyacetophenone
  参考文献：
  名称：

  一种儿茶素类化合物的制备方法

  摘要：

  本发明涉及一种儿茶素类化合物的制备方法，所述的方法以2,4,6-三羟基苯乙酮，对羟基苯甲醛为原料，经缩合反应，还原脱氧，环氧化，酸催化的环合反应得到儿茶素类化合物。本发明优点在于：本发明提供一种可用于生产儿茶素类化合物工艺。在中间体9的合成过程中，本发明利用路易斯酸催化的硼氢化钠还原从而大大降低了由于双键转移而产生的副反应，而利用双氧水氧化代替了剧毒试剂四氧化锇。

  公开号：

  CN103833720B

文献信息

• 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。
• Regioselective Synthesis of Prenylisoflavones. Syntheses of Allolicoisoflavone A, 2,3-Dehydrokievitone, and Related Compounds
  作者：Masao Tsukayama、He Li、Ken Tsurumoto、Masaki Nishiuchi、Yasuhiko Kawamura

  DOI：10.1246/bcsj.71.2673

  日期：1998.11

  The palladium-catalyzed coupling reaction of 2′,4′,5,7-tetrakis(benzyloxy)-5′-iodoisoflavone (12), synthesized from the 5-iodochalcone 9, with 2-methyl-3-butyn-2-ol gave the corresponding 5′-(3-hydroxy-3-methyl-1-butynyl)isoflavone 13. The catalytic hydrogenation of 13 gave 2′,4′,5,7-tetrahydroxy-5′-(3-hydroxy-3-methylbutyl)isoflavone (2). Dehydration of the benzoate 14 of 2 afforded a mixture of

  钯催化的 2',4',5,7-四(苄氧基)-5'-碘异黄酮 (12) 与 2-methyl-3-butyn-2-ol 的偶联反应，由 5-iodochalcone 9 合成得到相应的5'-(3-羟基-3-甲基-1-丁炔基)异黄酮13。13的催化氢化得到2',4',5,7-四羟基-5'-(3-羟基-3-甲基丁基）异黄酮（2）。2 的苯甲酸酯 14 脱水得到 5'-（3-甲基-2-丁烯基）异黄酮 15 和异构体 5'-（3-甲基-3-丁烯基）异黄酮 16 的混合物。 15 的分离通过以下方式完成用硝酸汞(II)处理混合物(15和16)。15 的水解得到 2',4',5,7-tetrahydroxy-5'-prenylisoflavone (allolicoisoflavone A) (1)。以类似的方式，2',4',5,7-tetrahydroxy-8-prenylisoflavone (2,3-dehydrokievitone)
• 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）。
• Facile synthesis of polyhydroxycoumaronochromones with quinones: synthesis of alkylpolyhydroxy- and alkoxycoumaronochromones from 2′-hydroxyisoflavones
  作者：Masao Tsukayama、Akihiro Oda、Yasuhiko Kawamura、Masaki Nishiuchi、Kazuyo Yamashita

  DOI：10.1016/s0040-4039(01)01234-5

  日期：2001.8

  4 ' ,5,7-Trihydroxy- or 8-alkyl-4 ' .5,7-trihvclroxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with o-chloranil under mild conditions. By contrast, alkoxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with DDQ. (C) 2001 Elsevier Science 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.