8,8-dimethyl-2-(tributylstannyl)methyl-3-(Z)-(trimethylsilyl)methylidene-7,9-dioxaspiro[4.5]decane | 345666-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8,8-dimethyl-2-(tributylstannyl)methyl-3-(Z)-(trimethylsilyl)methylidene-7,9-dioxaspiro[4.5]decane
• 英文别名: [(Z)-[8,8-dimethyl-2-(tributylstannylmethyl)-7,9-dioxaspiro[4.5]decan-3-ylidene]methyl]-trimethylsilane
• CAS: 345666-60-6
• 化学式: C₂₇H₅₄O₂SiSn
• 分子量: 557.52
• InChiKey: MTTIGBAXICJYNN-FEGRSWJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  叔丁基锡烷 、 5-allyl-2,2-dimethyl-5-(prop-2-yn-1-yl)-1,3-dioxane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (1/1) 作用下， 以 四氢呋喃 为溶剂， 以24%的产率得到8,8-dimethyl-2-(tributylstannyl)methyl-3-(Z)-(trimethylsilyl)methylidene-7,9-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Further studies on palladium-catalyzed bismetallative cyclization of enynes in the presence of Bu3SnSiMe3

  摘要：

  Bismetallative cyclization of enynes with Bu3SnSiMe3 catalyzed by Pd(0) complex was realized for the first time, which gives cyclized products containing a vinylsilane moiety and a homoallyltin moiety in good yield. In this cyclization, Pd-2(dba)(3)(CHCl3)-C-. or Pd(OH)2 on charcoal is effective as a Pd(0) catalyst and the addition of a phosphine ligand increased the formation of alkyne bismetallation by-product. On the other hand, it was found that a nucleophilic N-heterocyclic carbene could be utilized as a ligand for this cyclization. The utility of the cyclized products obtained from this cyclization in synthetic organic chemistry have been proven by transformation into cyclopropanol derivatives. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00601-6

文献信息

• Palladium-Catalyzed Bismetallative Cyclization of Enynes
  作者：Miwako Mori、Tomohiro Hirose、Hideaki Wakamatsu、Noriko Imakuni、Yoshihiro Sato

  DOI：10.1021/om000979x

  日期：2001.5.1

  Enynes were reacted with Me3SiSnBu3 in the presence of Pd(2)dba(3). CHCl3 or Pd(OH)(2) on charcoal to give cyclized products containing a vinylsilane moiety and a homoallyltin moiety in good yield.