1-(8a-methyl-3,4,4a,7,8,8a-hexahydronaphthalen-2-yl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(8a-methyl-3,4,4a,7,8,8a-hexahydronaphthalen-2-yl)ethan-1-one
• 英文别名: 1-[(4aR,8aS)-8a-methyl-4,4a,7,8-tetrahydro-3H-naphthalen-2-yl]ethanone
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: LCXBFHBHAQRFHI-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基环戊烯 在 正丁基锂 、 三氟化硼乙醚 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 1-(8a-methyl-3,4,4a,7,8,8a-hexahydronaphthalen-2-yl)ethan-1-one
  参考文献：
  名称：

  Ready Access to Functionally Embellished cis-Hydrindanes and cis-Decalins: Protecting Group-Free Total Syntheses of (±)-Nootkatone and (±)-Noreremophilane

  摘要：

  A simple and efficient synthesis of functionalized cis-hydrindanes and cis-decalins was achieved using a sequential Diels-Alder/aldol approach in a highly diastereoselective manner. The scope of this method was tested with a variety of substrates and was successfully applied to the synthesis of two natural products in racemic form. The highlights of the present work provide ready access to 13 new cis-hydrindanes/cis-decalins, a protecting group-free total synthesis of an insect repellent Nootkatone, and the first synthesis of a Noreremophilane using the shortest sequence.

  DOI：

  10.1021/jo401033j

文献信息

• Ready Access to Functionally Embellished <i>cis</i>-Hydrindanes and <i>cis</i>-Decalins: Protecting Group-Free Total Syntheses of (±)-Nootkatone and (±)-Noreremophilane
  作者：Kishor L. Handore、B. Seetharamsingh、D. Srinivasa Reddy

  DOI：10.1021/jo401033j

  日期：2013.8.16

  A simple and efficient synthesis of functionalized cis-hydrindanes and cis-decalins was achieved using a sequential Diels-Alder/aldol approach in a highly diastereoselective manner. The scope of this method was tested with a variety of substrates and was successfully applied to the synthesis of two natural products in racemic form. The highlights of the present work provide ready access to 13 new cis-hydrindanes/cis-decalins, a protecting group-free total synthesis of an insect repellent Nootkatone, and the first synthesis of a Noreremophilane using the shortest sequence.