calyxin F | 205313-09-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: calyxin F
• 英文别名: (E)-1-[(2S,4R)-5-hydroxy-4-[(2S)-2-hydroxy-4-(4-hydroxyphenyl)butyl]-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-chromen-6-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 205313-09-3
• 化学式: C₃₅H₃₄O₈
• 分子量: 582.65
• InChiKey: PJTIQSBLAQYLNP-NWPOAFIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  calyxin F 在 pyridine-SO3 complex 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以70%的产率得到1-{(2S,4S)-5-Hydroxy-2-(4-hydroxy-phenyl)-6-[(Z)-3-(4-hydroxy-phenyl)-acryloyl]-7-methoxy-chroman-4-yl}-4-(4-hydroxy-phenyl)-butan-2-one
  参考文献：
  名称：

  Synthesis and Structure Revision of Calyxin Natural Products

  摘要：

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.

  DOI：

  10.1021/jo060094g
• 作为产物：
  描述：

  1-{(2S,4S)-5-Hydroxy-2-(4-hydroxy-phenyl)-6-[(Z)-3-(4-hydroxy-phenyl)-acryloyl]-7-methoxy-chroman-4-yl}-4-(4-hydroxy-phenyl)-butan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-epicalyxin F 、 calyxin F
  参考文献：
  名称：

  Synthesis and Structure Revision of Calyxin Natural Products

  摘要：

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.

  DOI：

  10.1021/jo060094g

文献信息

• Synthesis and Structure Revision of Calyxin Natural Products
  作者：Xia Tian、James J. Jaber、Scott D. Rychnovsky

  DOI：10.1021/jo060094g

  日期：2006.4.1

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.