2-(tert-butyldimethylsilanyloxy)-6-hydroxy-7-trityloxynona-4,8-dien-3-one | 872035-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(tert-butyldimethylsilanyloxy)-6-hydroxy-7-trityloxynona-4,8-dien-3-one
• 英文别名: (2S,4E,6S,7S)-2-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-7-trityloxynona-4,8-dien-3-one
• CAS: 872035-34-2
• 化学式: C₃₄H₄₂O₄Si
• 分子量: 542.791
• InChiKey: DHXRAHWGAYDQMS-ACJDOOJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.45
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilanyloxy)-6-hydroxy-7-trityloxynona-4,8-dien-3-one 在 4-二甲氨基吡啶 、 Hoveyda-Grubbs catalyst second generation 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 141.0h， 生成 6-[4-(tert-butyldimethylsilanyloxy)-3-oxopent-1-enyl]-5-hydroxy-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (+)-Phomopsolide C by Ring-Size Selective Ring-Closing Metathesis/Cross-Metathesis

  摘要：

  A new strategy for the synthesis of chiral 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones by ring-size selective ring-closing metathesis (RCM) and its application to a short total synthesis of (+)-phomopsolide C are described. The key bond-forming reactions in this approach are a chemoselective cross-metathesis (CM) and RCM.

  DOI：

  10.1021/ol052332k
• 作为产物：
  描述：

  (s)-(-)-2-(叔丁基二甲基甲硅烷基氧基)丙酸乙酯 在 Hoveyda-Grubbs catalyst second generation 异丙基氯化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 2-(tert-butyldimethylsilanyloxy)-6-hydroxy-7-trityloxynona-4,8-dien-3-one
  参考文献：
  名称：

  Total Synthesis of (+)-Phomopsolide C by Ring-Size Selective Ring-Closing Metathesis/Cross-Metathesis

  摘要：

  A new strategy for the synthesis of chiral 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones by ring-size selective ring-closing metathesis (RCM) and its application to a short total synthesis of (+)-phomopsolide C are described. The key bond-forming reactions in this approach are a chemoselective cross-metathesis (CM) and RCM.

  DOI：

  10.1021/ol052332k

文献信息

• Total Synthesis of (+)-Phomopsolide C by Ring-Size Selective Ring-Closing Metathesis/Cross-Metathesis
  作者：Simon Michaelis、Siegfried Blechert

  DOI：10.1021/ol052332k

  日期：2005.11.1

  A new strategy for the synthesis of chiral 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones by ring-size selective ring-closing metathesis (RCM) and its application to a short total synthesis of (+)-phomopsolide C are described. The key bond-forming reactions in this approach are a chemoselective cross-metathesis (CM) and RCM.