[3,5-Dibenzoyloxy-4-(2-phenylmethoxyacetyl)phenyl] benzoate | 1616280-20-6

• 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: [3,5-Dibenzoyloxy-4-(2-phenylmethoxyacetyl)phenyl] benzoate
• CAS: 1616280-20-6
• 化学式: C₃₆H₂₆O₈
• 分子量: 586.598
• InChiKey: XMXQQYYOYOXHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [3,5-Dibenzoyloxy-4-(2-phenylmethoxyacetyl)phenyl] benzoate 在 四(三苯基膦)钯 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 43.17h， 生成 galangin
  参考文献：
  名称：

  Gram-scale synthesis of anti-pancreatic flavonoids (±)-8-[1-(4′-hydroxy-3′-methoxyphenyl)prop-2-en-1-yl]-chrysin and -galangin

  摘要：

  Gram-scale total synthesis of (+/-)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin (1) and -chrysin (2) has been accomplished in eight steps from commercially available phloroglucinol and three steps from commercially available chrysin, respectively, featuring an efficient introduction of C(8) (1-prop-2-en-1-yl)phenyl moiety in the natural products through chemo- and regioselective cinnamylation and regioselective aromatic Claisen rearrangement. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.057
• 作为产物：
  描述：

  苄氧基乙酰氯 在 4-二甲氨基吡啶 、 aluminum (III) chloride 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 [3,5-Dibenzoyloxy-4-(2-phenylmethoxyacetyl)phenyl] benzoate
  参考文献：
  名称：

  Gram-scale synthesis of anti-pancreatic flavonoids (±)-8-[1-(4′-hydroxy-3′-methoxyphenyl)prop-2-en-1-yl]-chrysin and -galangin

  摘要：

  Gram-scale total synthesis of (+/-)-8-[1-(4'-hydroxy-3'-methoxyphenyl)prop-2-en-1-yl]-galangin (1) and -chrysin (2) has been accomplished in eight steps from commercially available phloroglucinol and three steps from commercially available chrysin, respectively, featuring an efficient introduction of C(8) (1-prop-2-en-1-yl)phenyl moiety in the natural products through chemo- and regioselective cinnamylation and regioselective aromatic Claisen rearrangement. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.057

文献信息

• Total Synthesis of Acetylcholinesterase Inhibitor Macakurzin C
  作者：Hyoungsu Kim、Dongjoo Lee、Iljin Shin、Eunjae Ko、Kiyoun Lee、Seung-Yong Seo

  DOI：10.1055/s-0034-1378904

  日期：——

  A concise total synthesis of macakurzin C has been accomplished in nine steps (21% overall yield) from commercially available phloroglucinol, featuring a sequential aromatic Claisen rearrangement-cyclization.