(1aR,3aR,6S,7aS,7bR)-octahydro-3a,7b-dimethyl-6-(1-methylethenyl)-naphtho[2,1-b]oxiren-2(1aH)-one | 1007586-31-3

• 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,3aR,6S,7aS,7bR)-octahydro-3a,7b-dimethyl-6-(1-methylethenyl)-naphtho[2,1-b]oxiren-2(1aH)-one
• 英文别名: (1aR,3aR,6S,7aS,7bR)-3a,7b-dimethyl-6-prop-1-en-2-yl-3,4,5,6,7,7a-hexahydro-1aH-naphtho[1,2-b]oxiren-2-one
• CAS: 1007586-31-3
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: SAXBUQRXBICUSF-HWKXDMQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  O-(1aR,3aR,4RS,6R,7aS,7bR)-decahydro-3a,7b-dimethyl-6-(1-methylethenyl)-2-oxo-naphtho[2,1-b]oxiren-4-yl S-methyl carbonodithioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以91%的产率得到(1aR,3aR,6S,7aS,7bR)-octahydro-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

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.