16β-tetrahydrogibberellate diacetate | 959395-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 16β-tetrahydrogibberellate diacetate
• 英文别名: (1R,2R,5S,6S,8S,9S,10R,11S,12S)-5,12-diacetyloxy-6,11-dimethyl-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
• CAS: 959395-36-9
• 化学式: C₂₃H₃₀O₈
• 分子量: 434.486
• InChiKey: NSWRGTBXGWFCEL-XTRODJPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  16β-tetrahydrogibberellate diacetate 在 [Fe(II)(PDP)(CH₃CN)2](SbF₆)2 、 双氧水 作用下， 以 乙腈 为溶剂， 反应 1.25h， 以51%的产率得到[(1R,2R,5S,7R,8S,11S,12R,13S,14S,19S)-5-acetyloxy-13,19-dimethyl-10,18-dioxo-9,17-dioxahexacyclo[11.3.2.15,8.01,12.02,7.07,11]nonadecan-14-yl] acetate
  参考文献：
  名称：

  The Fe(PDP)-catalyzed aliphatic C–H oxidation: a slow addition protocol

  摘要：

  This report describes a slow addition protocol for the Fe(PDP)-catalyzecl aliphatic C-H oxidation reaction. Under this protocol, the reaction can be productively driven to higher conversions without decreasing site-selectivity or chemoselectivity. The operational advantages of this procedure are highlighted in the oxidation of two complex natural product derivatives. Hydroxylated products can be obtained in high isolated yields without the need for recycling recovered starting materials. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.11.082