benzyl (3S)-1-(2-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-1-diazo-4-methyl-2-oxopentan-3-ylcarbamate | 1204501-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (3S)-1-(2-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-1-diazo-4-methyl-2-oxopentan-3-ylcarbamate
• 英文别名: benzyl N-[(3S)-1-[2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxycyclohexyl]-1-diazo-4-methyl-2-oxopentan-3-yl]carbamate
• CAS: 1204501-05-2
• 化学式: C₂₆H₄₁N₃O₅Si
• 分子量: 503.714
• InChiKey: KQVHYKNGAZSOTQ-WRDKKKNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (3S)-1-(2-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-1-diazo-4-methyl-2-oxopentan-3-ylcarbamate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到(S)-benzyl 2-methyl-4,11-dioxoundec-5-yn-3-ylcarbamate
  参考文献：
  名称：

  Preparation of Tethered Aldehyde Ynoates and Ynones by Ring Fragmentation of Cyclic γ-Oxy-β-hydroxy-α-diazo Carbonyls

  摘要：

  Cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls undergo Lewis acid induced ring fragmentation to provide either ynoates or ynones tethered to an aldehyde, ketone, or ester. The fragmentation precursors are convenient to prepare by adding lithiated alpha-diazo carbonyls to alpha-oxy ketones. The fragmentation appears general and provides a variety of functional group-rich products in good to excellent yield.

  DOI：

  10.1021/jo902405f
• 作为产物：
  描述：

  2-(叔丁基二甲基硅杂氧基)环己酮 、 benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate 在 正丁基锂 、 二异丙胺 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以80%的产率得到benzyl (3S)-1-(2-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-1-diazo-4-methyl-2-oxopentan-3-ylcarbamate
  参考文献：
  名称：

  Preparation of Tethered Aldehyde Ynoates and Ynones by Ring Fragmentation of Cyclic γ-Oxy-β-hydroxy-α-diazo Carbonyls

  摘要：

  Cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls undergo Lewis acid induced ring fragmentation to provide either ynoates or ynones tethered to an aldehyde, ketone, or ester. The fragmentation precursors are convenient to prepare by adding lithiated alpha-diazo carbonyls to alpha-oxy ketones. The fragmentation appears general and provides a variety of functional group-rich products in good to excellent yield.

  DOI：

  10.1021/jo902405f