6-deuteriodihydrocelastrol | 1350630-31-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6-deuteriodihydrocelastrol
• CAS: 1350630-31-7
• 化学式: C₂₉H₄₀O₄
• 分子量: 453.626
• InChiKey: WZAUFGYINZYCKH-YFODWJJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  33.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  77.76
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  雷公藤红素 在 硼氘化钠 、 盐酸 作用下， 以 Methanol-d6 、 水 为溶剂， 反应 0.17h， 生成 6-deuteriodihydrocelastrol
  参考文献：
  名称：

  Remarkable Stereospecific Conjugate Additions to the Hsp90 Inhibitor Celastrol

  摘要：

  Celastrol, an important natural product and Hsp90 inhibitor with a wide range of biological and medical activities and broad use as a biological probe, acts by an as yet undetermined mode of action. It is known to undergo Michael additions with biological sulfur nucleophiles. Here it is demonstrated that nucleophiles add to the pharmacophore of celastrol in a remarkable stereospecific manner. Extensive characterization of the addition products has been obtained using NMR spectrometry, nuclear Overhauser effects, and density functional theory to determine facial selectivity and gain insight into the orbital interactions of the reactive centers. This stereospecificity of celastrol may be important to its protein target selectivity.

  DOI：

  10.1021/ja208359a