(S)-griffonianone D

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: (S)-griffonianone D
• 英文别名: 7-[(E,6S)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]-3-(4-methoxyphenyl)chromen-4-one
• 化学式: C₂₆H₃₀O₆
• 分子量: 438.521
• InChiKey: AQMCMECFWIVQQR-VRBZIXIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  刺芒柄花素 在 偶氮二甲酸二异丙酯 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 11.0h， 生成 (S)-griffonianone D
  参考文献：
  名称：

  Practical and efficient entry to isoflavones by Pd(0)/C-mediated Suzuki–Miyaura reaction. Total synthesis of geranylated isoflavones

  摘要：

  A scalable synthesis of isoflavones taking advantage of the Suzuki-Miyaura reaction catalyzed by Pd(0)/C is described. The approach developed has been extended to the total synthesis of 7-O-geranylformononetin, griffonianone D, and conrauinone D, which did not display cytotoxicity against human HeLa carcinoma cells. In addition, this study established unambiguously the absolute configuration of natural griffonianone D. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.062

文献信息

• Practical and efficient entry to isoflavones by Pd(0)/C-mediated Suzuki–Miyaura reaction. Total synthesis of geranylated isoflavones
  作者：François-Xavier Felpin、Cécile Lory、Hawaa Sow、Samir Acherar

  DOI：10.1016/j.tet.2007.01.062

  日期：2007.4

  A scalable synthesis of isoflavones taking advantage of the Suzuki-Miyaura reaction catalyzed by Pd(0)/C is described. The approach developed has been extended to the total synthesis of 7-O-geranylformononetin, griffonianone D, and conrauinone D, which did not display cytotoxicity against human HeLa carcinoma cells. In addition, this study established unambiguously the absolute configuration of natural griffonianone D. (c) 2007 Elsevier Ltd. All rights reserved.