4-acetyloxy-3,5-dimethoxycinnamic anhydride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-acetyloxy-3,5-dimethoxycinnamic anhydride
• 英文别名: 3-(4-Acetyloxy-3,5-dimethoxyphenyl)prop-2-enoyl 3-(4-acetyloxy-3,5-dimethoxyphenyl)prop-2-enoate；3-(4-acetyloxy-3,5-dimethoxyphenyl)prop-2-enoyl 3-(4-acetyloxy-3,5-dimethoxyphenyl)prop-2-enoate
• 化学式: C₂₆H₂₆O₁₁
• 分子量: 514.486
• InChiKey: VOUJQHSYRSNXFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-acetyloxy-3,5-dimethoxycinnamic anhydride 在 偶氮二甲酸二异丙酯 、 ammonium acetate 、 水 、 三乙胺 、 三苯基膦 、 cobalt(II) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 a-D-吡喃葡萄糖苷,3-O-[(2E)-3-(4-羟基-3,5-二甲氧苯基)-1-羰基-2-丙烯-1-基]-b-D-果呋喃糖基,6-(4-羟基苯酸酯)
  参考文献：
  名称：

  Studies on the total synthesis of tenuifoliside B

  摘要：

  An efficient synthesis of tenuifoliside B, which shows potential cognitive improvement and cerebral protective effects that may be further developed to become an anti-AD lead compound, has been developed starting from commercial available starting materials. Regioselective introductions of acyl groups to the OH-3' and OH-6 of sucrose play the key steps by metal chelate-directed acylation and Mitsunobu esterification, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.050
• 作为产物：
  描述：

  (E)-4-acetoxy-3,5-dimethoxycinnamic acid 在 三光气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 0.42h， 以82%的产率得到4-acetyloxy-3,5-dimethoxycinnamic anhydride
  参考文献：
  名称：

  Studies on the total synthesis of tenuifoliside B

  摘要：

  An efficient synthesis of tenuifoliside B, which shows potential cognitive improvement and cerebral protective effects that may be further developed to become an anti-AD lead compound, has been developed starting from commercial available starting materials. Regioselective introductions of acyl groups to the OH-3' and OH-6 of sucrose play the key steps by metal chelate-directed acylation and Mitsunobu esterification, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.050

文献信息

• Studies on the total synthesis of tenuifoliside B
  作者：Yongjiang Wu、Qiyuan Shi、Houliang Lei、Xuesong Liu、Lianjun Luan

  DOI：10.1016/j.tet.2014.04.050

  日期：2014.6

  An efficient synthesis of tenuifoliside B, which shows potential cognitive improvement and cerebral protective effects that may be further developed to become an anti-AD lead compound, has been developed starting from commercial available starting materials. Regioselective introductions of acyl groups to the OH-3' and OH-6 of sucrose play the key steps by metal chelate-directed acylation and Mitsunobu esterification, respectively. (C) 2014 Elsevier Ltd. All rights reserved.