(tert-butyl)(2-methyl-5-methylenetetrahydropyran-2-ylmethoxy)diphenylsilane | 1012075-20-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (tert-butyl)(2-methyl-5-methylenetetrahydropyran-2-ylmethoxy)diphenylsilane
• 英文别名: Tert-butyl-[(2-methyl-5-methylideneoxan-2-yl)methoxy]-diphenylsilane
• CAS: 1012075-20-5
• 化学式: C₂₄H₃₂O₂Si
• 分子量: 380.602
• InChiKey: ZEIYKKFMSLNLEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-(tert-butyldiphenylsilyloxy)-5-methyl-2-methylenehexane-1,5-diol 在 palladium diacetate titanium(IV) isopropylate 、 4 A molecular sieve 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以38%的产率得到(tert-butyl)(2-methyl-5-methylenetetrahydropyran-2-ylmethoxy)diphenylsilane
  参考文献：
  名称：

  Investigation of an Organomagnesium-Based [3 + 3] Annelation to Pyrans and Its Application in the Synthesis of Rhopaloic Acid A

  摘要：

  [GRAPHICS]A stepwise [3 + 3] annelation reaction has been developed that allows access to pyrans from epoxides. This process involves the addition of an allylmagnesium reagent, itself readily prepared from methallyl alcohol, and a Pd-catalyzed cyclodehydration reaction. The potential of this process to be employed in natural product synthesis has been exemplified by its use in the preparation of rhopaloic acid A.

  DOI：

  10.1021/jo702620e

文献信息

• Investigation of an Organomagnesium-Based [3 + 3] Annelation to Pyrans and Its Application in the Synthesis of Rhopaloic Acid A
  作者：Julien C. R. Brioche、Katharine M. Goodenough、David J. Whatrup、Joseph P. A. Harrity

  DOI：10.1021/jo702620e

  日期：2008.3.1

  [GRAPHICS]A stepwise [3 + 3] annelation reaction has been developed that allows access to pyrans from epoxides. This process involves the addition of an allylmagnesium reagent, itself readily prepared from methallyl alcohol, and a Pd-catalyzed cyclodehydration reaction. The potential of this process to be employed in natural product synthesis has been exemplified by its use in the preparation of rhopaloic acid A.