triethoxy(7-methoxybenzo[d][1,3]dioxol-5-yl)silane | 1449012-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: triethoxy(7-methoxybenzo[d][1,3]dioxol-5-yl)silane
• CAS: 1449012-55-8
• 化学式: C₁₄H₂₂O₆Si
• 分子量: 314.411
• InChiKey: YEVHJZWBQCOXEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  triethoxy(7-methoxybenzo[d][1,3]dioxol-5-yl)silane 、 methyl 7-(ethoxycarbonyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-ylcarbamate 在 Pd(COD)(NQ) 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以30%的产率得到methyl ((3aS,4R,5R,7aR)-7'-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydro-[5,5'-bibenzo[d][1,3]dioxol]-4-yl)carbamate
  参考文献：
  名称：

  Advances in Siloxane-Based Coupling Reactions: Application of Palladium-Mediated Allyl-Aryl Coupling to the Synthesis of Pancratistatin Derivatives. The Formal Total Synthesis of (±)-7-Deoxypancratistatin

  摘要：

  Palladium-mediated coupling of an allylic carbonate and an aryl siloxane has been applied to the formal total synthesis of 7-deoxypancratistatin and pancratistatin analogues. The key coupling reaction involved the use of a novel palladium olefin complex resulting in regio- and stereoselective arylation yielding a tetracyclic A-C ring intermediate. The observed regioselectivity of the coupling reaction was consistent with a model in which an unsymmetrical pi-allyl palladium complex was formed. Coupling of a variety of substituted phenyl siloxane derivatives was achieved using the new Pd(0) system to provide access to novel pancratistatin derivatives.

  DOI：

  10.3987/com-12-s(n)35
• 作为产物：
  描述：

  硅酸四乙酯 、 4-甲氧基-6-溴-1,3-苯并二噁茂 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以50%的产率得到triethoxy(7-methoxybenzo[d][1,3]dioxol-5-yl)silane
  参考文献：
  名称：

  Advances in Siloxane-Based Coupling Reactions: Application of Palladium-Mediated Allyl-Aryl Coupling to the Synthesis of Pancratistatin Derivatives. The Formal Total Synthesis of (±)-7-Deoxypancratistatin

  摘要：

  Palladium-mediated coupling of an allylic carbonate and an aryl siloxane has been applied to the formal total synthesis of 7-deoxypancratistatin and pancratistatin analogues. The key coupling reaction involved the use of a novel palladium olefin complex resulting in regio- and stereoselective arylation yielding a tetracyclic A-C ring intermediate. The observed regioselectivity of the coupling reaction was consistent with a model in which an unsymmetrical pi-allyl palladium complex was formed. Coupling of a variety of substituted phenyl siloxane derivatives was achieved using the new Pd(0) system to provide access to novel pancratistatin derivatives.

  DOI：

  10.3987/com-12-s(n)35