(Z)-(6-((2,3-dimethylbutan-2-yl)dimethylsilyl)hexa-3-en-1,5-diyn-1-yl)magnesium bromide | 129966-57-0

• 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: (Z)-(6-((2,3-dimethylbutan-2-yl)dimethylsilyl)hexa-3-en-1,5-diyn-1-yl)magnesium bromide
• CAS: 129966-57-0
• 化学式: C₁₄H₂₁BrMgSi
• 分子量: 321.615
• InChiKey: UPJYUDQXJYCATE-XXAVUKJNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (Z)-(6-((2,3-dimethylbutan-2-yl)dimethylsilyl)hexa-3-en-1,5-diyn-1-yl)magnesium bromide 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 3-((E)-3-Hydroxy-1-methyl-propenyl)-6-methoxy-2-((3Z,7E)-8-methoxycarbonyl-octa-3,7-diene-1,5-diynyl)-2H-quinoline-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Transannular Diels-Alder route to systems related to dynemicin A

  摘要：

  DOI：

  10.1021/ja00176a060
• 作为产物：
  描述：

  硅烷,[6-[二甲基(1,1,2-三甲基丙基)甲硅烷基]-3-己烯-1,5-二炔基]三甲基-,(Z)- 生成 (Z)-(6-((2,3-dimethylbutan-2-yl)dimethylsilyl)hexa-3-en-1,5-diyn-1-yl)magnesium bromide
  参考文献：
  名称：

  Transannular Diels-Alder route to systems related to dynemicin A

  摘要：

  DOI：

  10.1021/ja00176a060

文献信息

• Stereochemical and Conformational Effects on the Cycloaromatization of Dynemicin A-Related Molecules
  作者：Daniel Elbaum、John A. Jr. Porco、Thomas J. Stout、Jon Clardy、Stuart L. Schreiber

  DOI：10.1021/ja00106a025

  日期：1995.1

  A series of compounds was investigated in order to determine the factors that govern the cycloaromatization reaction exhibited by dynemicin A and related molecules. It was determined that the stereochemistry at C10a dictated the thermal reactivity of compounds equipped with an exo-epoxide. Structures containing an alpha-substituent were unreactive while those possessing a beta-substituent underwent cyclization at 80 degrees C. Molecular mechanics and dynamics calculations indicate that this reactivity difference is due to a steric interaction that develops as the alpha-substituted compounds undergo a conformational change that appears to be necessary for aromatization to occur. Additionally, a C10a alpha-substituted endo-epoxide was synthesized and shown to undergo cycloaromatization under mild acidic conditions via an epoxide opening.