(2R)-1,4-Dioxaspiro[4.4]nonane-2-carboxaldehyde | 120157-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-1,4-Dioxaspiro[4.4]nonane-2-carboxaldehyde
• 英文别名: (3R)-1,4-dioxaspiro[4.4]nonane-3-carbaldehyde
• CAS: 120157-64-4
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FXQLPHIRKYYRDF-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-1,4-Dioxaspiro[4.4]nonane-2-carboxaldehyde 、 (2S,3R)-3-(((tert-butyldiphenylsilyl)oxy)methyl)-1,4-dioxaspiro[4.4]nonane-2-carbaldehyde 、 2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane 在 (^lIpc)2BH 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以73%的产率得到(1R,5S,Z)-1-((2R,3R)-3-((tert-butyldiphenylsilyloxy)methyl)-1,4-dioxaspiro[4.4]nonan-2-yl)-5-((R)-1,4-dioxaspiro[4.4]nonan-2-yl)pent-2-ene-1,5-diol
  参考文献：
  名称：

  Concerning the Selective Protection of (Z)-1,5-syn-Ene-diols and (E)-1,5-anti-Ene-diols as Allylic Triethylsilyl Ethers

  摘要：

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.

  DOI：

  10.1021/ol702588h

文献信息

• Concerning the Selective Protection of (<i>Z</i>)-1,5-<i>syn</i>-Ene-diols and (<i>E</i>)-1,5-<i>anti</i>-Ene-diols as Allylic Triethylsilyl Ethers
  作者：Jacqueline D. Hicks、Chan Woo Huh、Ashley D. Legg、William R. Roush

  DOI：10.1021/ol702588h

  日期：2007.12.1

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.