(1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-6-[2-(4-nitrophenyl)ethynyl]-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol | 945624-86-2

• 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: (1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-6-[2-(4-nitrophenyl)ethynyl]-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 945624-86-2
• 化学式: C₁₇H₁₉NO₈
• 分子量: 365.34
• InChiKey: CZBHXMWGGAPBRO-GAGVYUBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-6-[2-(4-nitrophenyl)ethynyl]-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol 在 双(乙腈)氯化钯(II) 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以39%的产率得到
  参考文献：
  名称：

  Steric control in Pd-mediated cycloisomerization of sugar alkynols: documentation of a rare allylic epimerization

  摘要：

  Pd-mediated cycloisomerization of C3-alkynylated glucofuranosyl derivatives revealed a dominance of steric factors over electronic factors. However, the intermediate glycals were epimerized prior to the ketalization and afforded the more stable cis-fused bicyclic ketals. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.133
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-((4-nitrophenyl)ethynyl)tetrahydrofuro[2,3-d][1,3]dioxol-6-ol 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 以81%的产率得到(1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-6-[2-(4-nitrophenyl)ethynyl]-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
  参考文献：
  名称：

  Steric control in Pd-mediated cycloisomerization of sugar alkynols: documentation of a rare allylic epimerization

  摘要：

  Pd-mediated cycloisomerization of C3-alkynylated glucofuranosyl derivatives revealed a dominance of steric factors over electronic factors. However, the intermediate glycals were epimerized prior to the ketalization and afforded the more stable cis-fused bicyclic ketals. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.133