(1aR,1bR,2aR,2bS,5S,6aS,6bR)-decahydro-1b-methoxy-2b,6b-dimethyl-5-(1-methylethenyl)naphtho[1,2-b:3,4-b']bisoxirene | 1007586-47-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1aR,1bR,2aR,2bS,5S,6aS,6bR)-decahydro-1b-methoxy-2b,6b-dimethyl-5-(1-methylethenyl)naphtho[1,2-b:3,4-b']bisoxirene
• 英文别名: (1S,2R,4R,5R,7R,8S,10S)-4-methoxy-1,7-dimethyl-10-prop-1-en-2-yl-3,6-dioxatetracyclo[6.4.0.02,4.05,7]dodecane
• CAS: 1007586-47-1
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: RUZYIKZVZCNXNT-OBKMEXPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  34.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1aR,1bR,2aR,2bS,5S,6aS,6bR)-decahydro-1b-methoxy-2b,6b-dimethyl-5-(1-methylethenyl)naphtho[1,2-b:3,4-b']bisoxirene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以0.230 g的产率得到(1aR,3R,3aS,6S,7aS,7bR)-octahydro-3-hydroxy-3a,7b-dimethyl-6-(1-methylethenyl)-naphtho[2,1-b]oxiren-2(1aH)-one
  参考文献：
  名称：

  Enantiospecific Total Synthesis of Lairdinol A

  摘要：

  [GRAPHICS]The synthesis, of lairdinol A, a component of the host-selective phytotoxin depsilairdin, was achieved in 12 steps overall yield) without the use of protecting groups starting with the Diels-Alder reaction of (R)-carvone with 3-trimethylsilyloxy-1,3-pentadiene. The key step established the trans ring fusion by preferential epoxidation of a trans-fused enone in an equilibrating mixture of the cis-fused and transfused diastereomers (i.e., equivalent to a dynamic kinetic resolution of these isomers). The synthesis confirms the absolute configurations of lairdinol A and its enantiomer, cyperusol C.

  DOI：

  10.1021/jo7024465
• 作为产物：
  描述：

  甲醇 、 (1aR,3aR,6S,7aS,7bR)-octahydro-3a,7b-dimethyl-6-(1-methylethenyl)-naphtho[2,1-b]oxiren-2(1aH)-one 在 sodium hydroxide 、 碘苯二乙酸 作用下， 反应 1.0h， 生成 (1aR,1bR,2aR,2bS,5S,6aS,6bR)-decahydro-1b-methoxy-2b,6b-dimethyl-5-(1-methylethenyl)naphtho[1,2-b:3,4-b']bisoxirene
  参考文献：
  名称：

  Enantiospecific Total Synthesis of Lairdinol A

  摘要：

  [GRAPHICS]The synthesis, of lairdinol A, a component of the host-selective phytotoxin depsilairdin, was achieved in 12 steps overall yield) without the use of protecting groups starting with the Diels-Alder reaction of (R)-carvone with 3-trimethylsilyloxy-1,3-pentadiene. The key step established the trans ring fusion by preferential epoxidation of a trans-fused enone in an equilibrating mixture of the cis-fused and transfused diastereomers (i.e., equivalent to a dynamic kinetic resolution of these isomers). The synthesis confirms the absolute configurations of lairdinol A and its enantiomer, cyperusol C.

  DOI：

  10.1021/jo7024465

文献信息

• Enantiospecific Total Synthesis of Lairdinol A
  作者：Sandip G. Pardeshi、Dale E. Ward

  DOI：10.1021/jo7024465

  日期：2008.2.1

  [GRAPHICS]The synthesis, of lairdinol A, a component of the host-selective phytotoxin depsilairdin, was achieved in 12 steps overall yield) without the use of protecting groups starting with the Diels-Alder reaction of (R)-carvone with 3-trimethylsilyloxy-1,3-pentadiene. The key step established the trans ring fusion by preferential epoxidation of a trans-fused enone in an equilibrating mixture of the cis-fused and transfused diastereomers (i.e., equivalent to a dynamic kinetic resolution of these isomers). The synthesis confirms the absolute configurations of lairdinol A and its enantiomer, cyperusol C.