1-[[(2R,4S,5R)-4-ethenyl-2-methyl-1,3-dioxan-5-yl]oxy]but-3-en-2-one | 934278-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 1-[[(2R,4S,5R)-4-ethenyl-2-methyl-1,3-dioxan-5-yl]oxy]but-3-en-2-one
• CAS: 934278-95-2
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: XUDRTJKTELDJHK-DVVUODLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[[(2R,4S,5R)-4-ethenyl-2-methyl-1,3-dioxan-5-yl]oxy]but-3-en-2-one 在 palladium dihydroxide 、 Grubbs catalyst first generation 、 四(三苯基膦)钯 、 碳酸氢钠 N,N-二甲基丙烯基脲 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium tetrahydroborate 、 氢气 、 叔丁基锂 、 二甲基二环氧乙烷 、 双(三甲基硅烷基)氨基钾 、 三乙基硼氢化锂 、 戴斯-马丁氧化剂 、 lithium chloride 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 24.33h， 生成 (1S,3R,6R,8S,11R,13S,14R)-13-ethenyl-6,11-dimethyl-2,5,7,12-tetraoxatricyclo[9.4.0.03,8]pentadecan-14-ol
  参考文献：
  名称：

  Synthesis of the Fused Polyether Core of Hemibrevetoxin B by Two-Directional Ring-Closing Metathesis

  摘要：

  The tetracyclic fused polyether core of the marine natural product hemibrevetoxin B has been prepared in an efficient manner by using a strategy in which ring-closing metathesis (RCM) reactions were employed for ring synthesis. Simultaneous construction of the A and D rings was accomplished by double two-directional RCM of a tetraene.

  DOI：

  10.1021/ol0630651
• 作为产物：
  描述：

  1-(2-methyl-4-vinyl-[1,3]dioxan-5-yloxy)-3-(triphenyl-λ5-phosphanylidene)-propan-2-one 、 聚合甲醛 以 乙醚 为溶剂， 以97%的产率得到1-[[(2R,4S,5R)-4-ethenyl-2-methyl-1,3-dioxan-5-yl]oxy]but-3-en-2-one
  参考文献：
  名称：

  Synthesis of the Fused Polyether Core of Hemibrevetoxin B by Two-Directional Ring-Closing Metathesis

  摘要：

  The tetracyclic fused polyether core of the marine natural product hemibrevetoxin B has been prepared in an efficient manner by using a strategy in which ring-closing metathesis (RCM) reactions were employed for ring synthesis. Simultaneous construction of the A and D rings was accomplished by double two-directional RCM of a tetraene.

  DOI：

  10.1021/ol0630651

文献信息

• Synthesis of the Fused Polyether Core of Hemibrevetoxin B by Two-Directional Ring-Closing Metathesis
  作者：J. Stephen Clark、Damian M. Grainger、Alexandra A.-C. Ehkirch、Alexander J. Blake、Claire Wilson

  DOI：10.1021/ol0630651

  日期：2007.3.1

  The tetracyclic fused polyether core of the marine natural product hemibrevetoxin B has been prepared in an efficient manner by using a strategy in which ring-closing metathesis (RCM) reactions were employed for ring synthesis. Simultaneous construction of the A and D rings was accomplished by double two-directional RCM of a tetraene.