2',4'-dihydroxy-6'-(methoxymethoxy)acetophenone | 71386-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',4'-dihydroxy-6'-(methoxymethoxy)acetophenone
• 英文别名: 2',4'-dihydroxy-6'-methoxymethoxyacetophenone；4,6-dihydroxy-2-(methoxymethoxy)acetophenone；2,4,6-trihydroxyacetophenone；4',6'-Dihydroxy-2'-(methoxymethoxy)acetophenon；1-[2,4-Dihydroxy-6-(methoxymethoxy)phenyl]ethanone
• CAS: 71386-98-6
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: OTPIQWGHDXEZER-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  371.4±21.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 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：

  2',4'-dihydroxy-6'-(methoxymethoxy)acetophenone 在 盐酸 、 氢氧化钾 、 碘 、 potassium carbonate 、 过碘酸 作用下， 以 甲醇 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 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：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 碘 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 2',4'-dihydroxy-6'-(methoxymethoxy)acetophenone
  参考文献：
  名称：

  抗がん作用を有するベンゾチオフェン誘導体

  摘要：

  提供具有优良抗癌作用的新化合物。采用式（1）所表示的苯并噻吩衍生物或其药学上可接受的盐。其中，“R1为H，OH，卤素基，C1-12的烷基，烯基，炔基，醚基，烷基氨基或烷基硫基，取代/未取代的芳基，取代/未取代的苄基，或取代/未取代的在5-6位缩合的烷基或杂环；R2为H，OH，卤素基，C1-12的烷基，烯基，炔基，醚基，烷基氨基或烷基硫基；取代/未取代的芳基或取代/未取代的苄基”。【选图】图1

  公开号：

  JP2016141638A

文献信息

• Synthesis and antiangiogenic activity study of new hop chalcone Xanthohumol analogues
  作者：Elisa Nuti、Barbara Bassani、Caterina Camodeca、Lea Rosalia、AnnaRita Cantelmo、Cristina Gallo、Denisa Baci、Antonino Bruno、Elisabetta Orlandini、Susanna Nencetti、Douglas M. Noonan、Adriana Albini、Armando Rossello

  DOI：10.1016/j.ejmech.2017.07.024

  日期：2017.9

  Xanthohumol (XN), a naturally occurring prenylated chalcone from hops, have been widely reported. Here we describe the synthesis and study the antiangiogenic activity in vitro of a series of XN derivatives, where different substituents on the B-ring of the chalcone scaffold were inserted. The new XN derivatives inhibited human umbilical-vein endothelial cell (HUVEC) proliferation, adhesion, migration, invasion

  血管生成诱导是癌症的标志。Xanthohumol（XN）（一种来自啤酒花的天然异戊烯化查耳酮）的抗血管生成特性已被广泛报道。在这里，我们描述了一系列XN衍生物的合成和体外抗血管生成活性，其中在查尔酮骨架的B环上插入了不同的取代基。新的XN衍生物在体外以10μM的浓度抑制了人脐静脉内皮细胞（HUVEC）的增殖，粘附，迁移，侵袭以及它们形成毛细血管状结构的能力。初步结果表明，天然XN中存在的R中的酚羟基对于具有抗血管生成活性不是必需的。实际上，该系列中最有效的化合物13的特征在于R环上的对甲氧基和R 2环上的R 2的氟原子。这项研究为XN合成类似物用作癌症血管预防和化学预防剂的未来开发铺平了道路。
• 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）。
• Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates
  作者：Mingbao Zhang、G. Erik Jagdmann、Michael Van Zandt、Paul Beckett、Hagen Schroeter

  DOI：10.1016/j.tetasy.2013.02.012

  日期：2013.4

  Ten orthogonally protected (-)-epicatechin and 3'- or 4'-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates. (c) 2013 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.
• 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.