5-hydroxy-5-trimethylsilanylethynyl-cyclohex-1-enecarboxylic acid methyl ester | 156826-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-5-trimethylsilanylethynyl-cyclohex-1-enecarboxylic acid methyl ester
• 英文别名: Methyl 5-hydroxy-5-(2-trimethylsilylethynyl)cyclohexene-1-carboxylate
• CAS: 156826-19-6
• 化学式: C₁₃H₂₀O₃Si
• 分子量: 252.386
• InChiKey: MLDJHFQGRODVKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-5-trimethylsilanylethynyl-cyclohex-1-enecarboxylic acid methyl ester 在 2,6-二甲基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 四丙基高钌酸铵 、 4 A molecular sieve 、 二异丁基氢化铝 、 potassium carbonate 、 N-甲基吗啉氧化物 、 正丁胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.45h， 生成 5-(hex-3-ene-1,5-diynyl)-5-<(tert-butyldimethylsilyl)oxy>-cyclohex-1-enecarboxaldehyde
  参考文献：
  名称：

  Facile Synthesis of a Simplified Bicyclo[7.3.1] Esperamicin-Calicheamicin Enediyne Core

  摘要：

  An efficient non cobalt mediated route for the synthesis of a simplified bicycle [7.3.1]enediyne core of the naturally occurring calicheamicins and esperamicins is described. The key cyclization provides a single propargylic alcohol stereoisomer which is in the same relative configuration as that found in the naturally occurring calicheamicins and esperamicins. Selective functionalizations of the cyclized core via selenium dioxide oxidations are described. Installation of an enone chemical trigger provides a hydroxylated analog of a previously described biologically active synthetic enediyne.

  DOI：

  10.1016/s0040-4020(01)80632-3
• 作为产物：
  描述：

  methyl 5-oxo-1-cyclohexenecarboxylate 、 三甲基乙炔基硅 在 cerium(III) chloride 、 lithium hexamethyldisilazane 作用下， 生成 5-hydroxy-5-trimethylsilanylethynyl-cyclohex-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Facile Synthesis of a Simplified Bicyclo[7.3.1] Esperamicin-Calicheamicin Enediyne Core

  摘要：

  An efficient non cobalt mediated route for the synthesis of a simplified bicycle [7.3.1]enediyne core of the naturally occurring calicheamicins and esperamicins is described. The key cyclization provides a single propargylic alcohol stereoisomer which is in the same relative configuration as that found in the naturally occurring calicheamicins and esperamicins. Selective functionalizations of the cyclized core via selenium dioxide oxidations are described. Installation of an enone chemical trigger provides a hydroxylated analog of a previously described biologically active synthetic enediyne.

  DOI：

  10.1016/s0040-4020(01)80632-3

文献信息

• Facile Synthesis of a Simplified Bicyclo[7.3.1] Esperamicin-Calicheamicin Enediyne Core
  作者：John F. Kadow、Donald J. Cook、Terrence W. Doyle、David R. Langley、Kahnie M. Pham、Dolatrai M. Vyas、Mark D. Wittman

  DOI：10.1016/s0040-4020(01)80632-3

  日期：1994.1

  An efficient non cobalt mediated route for the synthesis of a simplified bicycle [7.3.1]enediyne core of the naturally occurring calicheamicins and esperamicins is described. The key cyclization provides a single propargylic alcohol stereoisomer which is in the same relative configuration as that found in the naturally occurring calicheamicins and esperamicins. Selective functionalizations of the cyclized core via selenium dioxide oxidations are described. Installation of an enone chemical trigger provides a hydroxylated analog of a previously described biologically active synthetic enediyne.