4a-hydro-20-taxusin carboxylic acid methyl ester | 1380425-20-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4a-hydro-20-taxusin carboxylic acid methyl ester
• 英文别名: methyl (1R,3R,4S,5S,8R,9R,10R,13S)-5,9,10,13-tetraacetyloxy-8,12,15,15-tetramethyltricyclo[9.3.1.03,8]pentadec-11-ene-4-carboxylate
• CAS: 1380425-20-6
• 化学式: C₂₉H₄₂O₁₀
• 分子量: 550.646
• InChiKey: WGKBUQCVLLMAHX-CRMXLOGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4a-hydro-20-taxusin carboxylic acid methyl ester 在 C₂₄H₃₂FeN₆⁽²⁺⁾*2F₆Sb^(1-) 、 双氧水 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 16.2h， 以29%的产率得到nortaxane methyl ester
  参考文献：
  名称：

  Directed Metal (Oxo) Aliphatic C–H Hydroxylations: Overriding Substrate Bias

  摘要：

  The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.

  DOI：

  10.1021/ja301685r
• 作为产物：
  描述：

  (3S,4R,4aR,6R,8S,11R,12R,12aR)-4-(hydroxymethyl)-9,12a,13,13-tetramethyl-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-6,10-methanobenzo[10]annulene-3,8,11,12-tetrayl tetraacetate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 水 、 戴斯-马丁氧化剂 、 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 4a-hydro-20-taxusin carboxylic acid methyl ester
  参考文献：
  名称：

  Directed Metal (Oxo) Aliphatic C–H Hydroxylations: Overriding Substrate Bias

  摘要：

  The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.

  DOI：

  10.1021/ja301685r