(2R,4aR,9aS)-2-methyl-4a,9a-dihydro-4H-[1,3]dioxino[5,4-b]oxepin-7-one | 934278-96-3

• 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: (2R,4aR,9aS)-2-methyl-4a,9a-dihydro-4H-[1,3]dioxino[5,4-b]oxepin-7-one
• CAS: 934278-96-3
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: BHGFBGQHBKBXRC-BWVDBABLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2R,4aR,9aS)-2-methyl-4a,9a-dihydro-4H-[1,3]dioxino[5,4-b]oxepin-7-one 在 palladium dihydroxide 三丁基膦 、 氢气 、 双氧水 、 叔丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 苯 为溶剂， 反应 4.0h， 生成 (2R,4aR,6S,7R,9aS)-2,7-dimethyl-6-prop-2-enyl-4,4a,6,8,9,9a-hexahydro-[1,3]dioxino[5,4-b]oxepin-7-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-[[(2R,4S,5R)-4-ethenyl-2-methyl-1,3-dioxan-5-yl]oxy]but-3-en-2-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到(2R,4aR,9aS)-2-methyl-4a,9a-dihydro-4H-[1,3]dioxino[5,4-b]oxepin-7-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

• Stereoselective Synthesis of Medium-Sized Cyclic Ethers by Sequential Ring-Closing Metathesis and Tsuji–Trost Allylation
  作者：James Skardon-Duncan、Michael Sparenberg、Alexandre Bayle、Sam Alexander、J. Stephen Clark

  DOI：10.1021/acs.orglett.8b01082

  日期：2018.5.4

  Fully functionalized medium-sized cyclic ethers, of the type found in fused polyether natural products, have been prepared by sequential ring-closing diene metathesis, conversion of the resulting cyclic enone into an allylic enol carbonate, and Tsuji–Trost allylation using a chiral palladium complex. Very high levels of diastereocontrol, favoring the diastereomer in which there is a cis relationship

  通过顺序闭环二烯复分解，将所得环状烯酮转化为烯丙基烯醇碳酸酯，以及使用手性钯进行Tsuji-Trost烯丙基化反应，可以制备在融合的聚醚天然产物中发现的类型的完全功能化的中型环状醚。复杂的。在催化剂控制和催化反应的情况下，可以获得非常高的非对映异构控制水平，有利于非对映异构体，其中在中环醚的C-2处的烯丙基与C-7 / C-8处的取代基之间存在顺式关系。底物对照是匹配的。
• 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.