1,1-bis(methoxycarbonyl)-3-(1-(tributylstannyl)-1-(methoxycarbonyl)methyl)-4-(Z)-(trimethylsilyl)methylidenecyclopentane | 345666-61-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1-bis(methoxycarbonyl)-3-(1-(tributylstannyl)-1-(methoxycarbonyl)methyl)-4-(Z)-(trimethylsilyl)methylidenecyclopentane
• CAS: 345666-61-7
• 化学式: C₂₈H₅₂O₆SiSn
• 分子量: 631.513
• InChiKey: NXVBUYKWECGXQY-DWRCFZOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  叔丁基锡烷 、 5-methoxycarbonyl-5-prop-2-ynylhex-2-enedioic acid dimethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (1/1) 作用下， 以 四氢呋喃 为溶剂， 以32%的产率得到1,1-bis(methoxycarbonyl)-3-(1-(tributylstannyl)-1-(methoxycarbonyl)methyl)-4-(Z)-(trimethylsilyl)methylidenecyclopentane
  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.
• Further studies on palladium-catalyzed bismetallative cyclization of enynes in the presence of Bu3SnSiMe3
  作者：Yoshihiro Sato、Noriko Imakuni、Tomohiro Hirose、Hideaki Wakamatsu、Miwako Mori

  DOI：10.1016/s0022-328x(03)00601-6

  日期：2003.12

  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.