(R)-1-((3aR,5R,6R,6aR)-6-ethynyl-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol | 1351933-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((3aR,5R,6R,6aR)-6-ethynyl-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol
• 英文别名: (1R)-1-[(3aR,5R,6R,6aR)-6-ethynyl-6-methoxy-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]prop-2-en-1-ol
• CAS: 1351933-09-9
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: INCKEMMVVSAYDT-BZNQNGANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-((3aR,5R,6R,6aR)-6-ethynyl-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 25.0h， 生成 (3aR,4aS,8aS,8bR)-8a-methoxy-2,2-dimethyl-8-methylene-4a,8,8a,8b-tetrahydrobenzofuro[2,3-d][1,3]dioxol-5(3aH)-one
  参考文献：
  名称：

  A Tandem Enyne/Ring Closing Metathesis Approach to 4-Methylene-2-cyclohexenols: An Efficient Entry to Otteliones and Loloanolides

  摘要：

  A short and efficient approach to a 4-methylene-2-cyclohexenone substructure present in ottellones and loloanolides Is described. This strategy involves a tandem enyne/ring closing metathesis as the key reaction to construct this labile core unit

  DOI：

  10.1021/ol2029838
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 吡啶 、 正丁基锂 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 34.0h， 生成 (R)-1-((3aR,5R,6R,6aR)-6-ethynyl-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-ol
  参考文献：
  名称：

  A Tandem Enyne/Ring Closing Metathesis Approach to 4-Methylene-2-cyclohexenols: An Efficient Entry to Otteliones and Loloanolides

  摘要：

  A short and efficient approach to a 4-methylene-2-cyclohexenone substructure present in ottellones and loloanolides Is described. This strategy involves a tandem enyne/ring closing metathesis as the key reaction to construct this labile core unit

  DOI：

  10.1021/ol2029838

文献信息

• A Tandem Enyne/Ring Closing Metathesis Approach to 4-Methylene-2-cyclohexenols: An Efficient Entry to Otteliones and Loloanolides
  作者：Vipul V. Betkekar、Samaresh Panda、Krishna P. Kaliappan

  DOI：10.1021/ol2029838

  日期：2012.1.6

  A short and efficient approach to a 4-methylene-2-cyclohexenone substructure present in ottellones and loloanolides Is described. This strategy involves a tandem enyne/ring closing metathesis as the key reaction to construct this labile core unit