(1-(tert-butyldimethylsilyloxy)-2-oxocyclooctyl)methyl 2-diazoacetate | 1613315-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-(tert-butyldimethylsilyloxy)-2-oxocyclooctyl)methyl 2-diazoacetate
• CAS: 1613315-97-1
• 化学式: C₁₇H₃₀N₂O₄Si
• 分子量: 354.522
• InChiKey: URMDPBSYSSXJPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  89.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1-(tert-butyldimethylsilyloxy)-2-oxocyclooctyl)methyl 2-diazoacetate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙基苯 为溶剂， 反应 24.0h， 以64%的产率得到rel-(3aS,9aR)-3a-((tert-butyldimethylsilyl)oxy)-3-diazo-9a-(hydroxymethyl)octahydrocycloocta[b]furan-2(3H)-one
  参考文献：
  名称：

  Fragmentation of Bicyclic γ-Silyloxy-β-hydroxy-α-diazolactones as an Approach to Ynolides

  摘要：

  Medium-sized ynolides were prepared by the Lewis acid-mediated fragmentation of bicyclic gamma-silyloxy-beta-hydroxy-alpha-diazolactones in which the C beta-C gamma bond is the ring fusion bond. Although these lactone fragmentation substrates reacted somewhat less efficiently than their carbocyclic counterparts, the fragmentation provided 11-membered ynolides in up to 84% yield. Unlike prior fragmentations of similar substrates, elevated temperatures were required to obtain optimum yields of the ynolide products. The ynolides reported herein have ring sizes of 10 or 11, which are the smallest reported to date.

  DOI：

  10.1021/jo500634d
• 作为产物：
  描述：

  (E)-(1,2-bis(tert-butyldimethylsilyloxy)cyclooct-2-enyl)methanol 在 吡啶 、 N,N′-双(对甲苯磺酰)肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 (1-(tert-butyldimethylsilyloxy)-2-oxocyclooctyl)methyl 2-diazoacetate
  参考文献：
  名称：

  Fragmentation of Bicyclic γ-Silyloxy-β-hydroxy-α-diazolactones as an Approach to Ynolides

  摘要：

  Medium-sized ynolides were prepared by the Lewis acid-mediated fragmentation of bicyclic gamma-silyloxy-beta-hydroxy-alpha-diazolactones in which the C beta-C gamma bond is the ring fusion bond. Although these lactone fragmentation substrates reacted somewhat less efficiently than their carbocyclic counterparts, the fragmentation provided 11-membered ynolides in up to 84% yield. Unlike prior fragmentations of similar substrates, elevated temperatures were required to obtain optimum yields of the ynolide products. The ynolides reported herein have ring sizes of 10 or 11, which are the smallest reported to date.

  DOI：

  10.1021/jo500634d