4,2',4'-tris(benzyloxy)-6'-hydroxy-3'-iodochalcone | 887149-27-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4,2',4'-tris(benzyloxy)-6'-hydroxy-3'-iodochalcone
• 英文别名: 1-[6-hydroxy-3-iodo-2,4-bis(phenylmethoxy)phenyl]-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 887149-27-1
• 化学式: C₃₆H₂₉IO₅
• 分子量: 668.528
• InChiKey: PENJQOLYEWBQGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.63
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,2',4'-tris(benzyloxy)-6'-hydroxy-3'-iodochalcone 在 羟基甲苯磺酰碘苯 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 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：

  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：

  2',4'-bis(benzyloxy)-3'-iodo-6'-(methoxymethoxy)acetophenone 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.0h， 生成 4,2',4'-tris(benzyloxy)-6'-hydroxy-3'-iodochalcone
  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

文献信息

• 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.