1-[6-benzoyloxy-2,4-bis(benzyloxy)-3'-iodophenyl]-2-[4-benzyloxyphenyl]-3,3-dimethyloxypropan-1-one | 911285-86-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 1-[6-benzoyloxy-2,4-bis(benzyloxy)-3'-iodophenyl]-2-[4-benzyloxyphenyl]-3,3-dimethyloxypropan-1-one
• 英文别名: 1-[6-benzoyloxy-2,4-bis(benzyloxy)-3-iodophenyl]-2-(4-benzyloxyphenyl)-3,3-dimethoxypropan-1-one；[2-[3,3-Dimethoxy-2-(4-phenylmethoxyphenyl)propanoyl]-4-iodo-3,5-bis(phenylmethoxy)phenyl] benzoate
• CAS: 911285-86-4
• 化学式: C₄₅H₃₉IO₈
• 分子量: 834.704
• InChiKey: VVFSDZNWXMANBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[6-benzoyloxy-2,4-bis(benzyloxy)-3'-iodophenyl]-2-[4-benzyloxyphenyl]-3,3-dimethyloxypropan-1-one 在 palladium on activated charcoal 、 palladium dichloride 甲醇 、 sodium hydroxide 、 copper(l) iodide 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 10.92h， 生成 [4-[7-Benzoyloxy-6-(3-methylbut-3-enyl)-5-(4-methylphenyl)sulfonyloxy-4-oxochromen-3-yl]phenyl] benzoate
  参考文献：
  名称：

  Regioselective Synthesis of 6‐Prenylpolyhydroxyisoflavone (Wighteone) and Wighteone Hydrate with Hypervalent Iodine

  摘要：

  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.

  DOI：

  10.1080/00397910500514121
• 作为产物：
  描述：

  4,2',4'-tris(benzyloxy)-3'-iodo-6'-methoxymethoxychalcone 在 吡啶 、 盐酸 、 羟基甲苯磺酰碘苯 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.28h， 生成 1-[6-benzoyloxy-2,4-bis(benzyloxy)-3'-iodophenyl]-2-[4-benzyloxyphenyl]-3,3-dimethyloxypropan-1-one
  参考文献：
  名称：

  Microwave-assisted regioselective synthesis of natural 6-prenylpolyhydroxyisoflavones and their hydrates with hypervalent iodine reagents

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.06.066

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。
• Synthesis of Isoflavones from 2′-Hydroxychalcones Using Poly[4-(diacetoxy)iodo]styrene or Related Hypervalent Iodine Reagent
  作者：Yasuhiko Kawamura、Masashi Maruyama、Takanori Tokuoka、Masao Tsukayama

  DOI：10.1055/s-2002-35617

  日期：——

  Isoflavones are synthesized in an one-pot reaction by treating the hypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent) with 2'-benzoyloxychalcones in McOH. A combined use of (diacetoxyiodo)benzene (DIB)/p-toluenesulfonic acid (TsOH) is also effective for the same purpose. As an extension of these monomeric reagents, polymer-supported DIB PSDIB, poly[4-(diacetoxy)iodo]styrene}

  通过在 McOH 中用 2'-苯甲酰氧基查耳酮处理高价碘 (III) 试剂 [羟基（甲苯磺酰氧基）碘] 苯（HTIB，Koser 试剂），在一锅法反应中合成异黄酮。(二乙酰氧基碘)苯(DIB)/对甲苯磺酸(TsOH)的组合使用对于相同的目的也是有效的。作为这些单体试剂的扩展，聚合物负载的 DIB PSDIB，聚 [4-(二乙酰氧基)碘]苯乙烯} 与 TsOH 也很有效。后者的优点是易于从反应混合物中分离异黄酮，不会释放 Phi，并且可以重复使用试剂。