2-(2,5,5-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanol | 183549-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,5,5-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanol
• 英文别名: (+/-)-nanaimool；nanaimool；2-(2,5,5-Trimethyl-1,3,4,6,7,8-hexahydronaphthalen-2-yl)ethanol
• CAS: 183549-63-5
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: BCRZEHCIGDIXBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,5,5-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2-(2,5,5-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)acetaldehyde
  参考文献：
  名称：

  Studies on the Synthesis of Acanthodoral and Nanaimoal:  Evaluation of Cationic Cyclization Routes

  摘要：

  Intramolecular Lewis acid-promoted reactions of alpha,beta-unsaturated ketone 6 and aldehydes 7 and 8 were examined as potential routes to acanthodoral (1), a structurally interesting natural product. Ketone 6 afforded ene product 22 exclusively, and both 7 and 8 gave mixtures of bicyclic aldehydes 3 and 26 and tricyclic aldehyde 25. The latter most likely results from 7 by intramolecular cyclization of the alkene onto the Lewis acid-activated carbonyl moiety affording carbocation 31 followed by a 1,2-hydride shift and ring closure. Starting from 8, tricyclic aldehyde 25 apparently forms by cyclization to cation 35 and ring closure to cyclobutane 36, followed by ring opening to 31, the same cation as formed in reactions of 7. Nanaimoal (3) results from loss of H+ from 31, and bicyclic aldehyde 26 may be formed in a similar manner or by a concerted ene reaction. The configuration of 25 establishes that the stereochemistry of the initial cyclization to 31 precludes the possible use of this strategy for the synthesis of acanthodoral. However, acid-promoted cyclization of allylic alcohol 23 efficiently gives diene 29 which undergoes selective hydroboration/oxidation to afford nanaimoal.

  DOI：

  10.1021/jo9610568
• 作为产物：
  描述：

  (E)-N,N-二乙基-3,7-二甲基-2,6-辛二烯-1-胺 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 双氧水 、 二异丁基氢化铝 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2-(2,5,5-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanol
  参考文献：
  名称：

  Synthesis of (±)-Nanaimoal and (±)-Nanaimool fromN,N-Diethylgeranylamine

  摘要：

  (±)-纳奈莫醇和(±)-纳奈莫醇是通过1,1-二甲基-2,3-二亚甲基环己烷的Diels-Alder反应合成的，这是一种新型的环状萜类化合物的构建块，易于从N,N-二乙基香叶胺制备。

  DOI：

  10.1246/cl.1993.29

文献信息

• Zeolite NaY-Promoted Cyclization of Farnesal:  A Short Route to Nanaimoal
  作者：Constantinos Tsangarakis、Ioannis N. Lykakis、Manolis Stratakis

  DOI：10.1021/jo7024527

  日期：2008.4.1

  The sesquiterpene nanaimoal was synthesized in 21% overall yield and in a biomimetic manner. As a key step, the acid-catalyzed cyclization of farnesal under zeolite NaY confinement conditions was used. The intrazeolite cyclization of farnesal affords as major product a double-bond isomer of nanaimoal, via a novel diastereoselective tandem 1,5-diene cyclization/Prins-type reaction.
• Studies on the Synthesis of Acanthodoral and Nanaimoal:  Evaluation of Cationic Cyclization Routes
  作者：Thomas A. Engler、Mohammed Hashmat Ali、Fusao Takusagawa

  DOI：10.1021/jo9610568

  日期：1996.1.1

  Intramolecular Lewis acid-promoted reactions of alpha,beta-unsaturated ketone 6 and aldehydes 7 and 8 were examined as potential routes to acanthodoral (1), a structurally interesting natural product. Ketone 6 afforded ene product 22 exclusively, and both 7 and 8 gave mixtures of bicyclic aldehydes 3 and 26 and tricyclic aldehyde 25. The latter most likely results from 7 by intramolecular cyclization of the alkene onto the Lewis acid-activated carbonyl moiety affording carbocation 31 followed by a 1,2-hydride shift and ring closure. Starting from 8, tricyclic aldehyde 25 apparently forms by cyclization to cation 35 and ring closure to cyclobutane 36, followed by ring opening to 31, the same cation as formed in reactions of 7. Nanaimoal (3) results from loss of H+ from 31, and bicyclic aldehyde 26 may be formed in a similar manner or by a concerted ene reaction. The configuration of 25 establishes that the stereochemistry of the initial cyclization to 31 precludes the possible use of this strategy for the synthesis of acanthodoral. However, acid-promoted cyclization of allylic alcohol 23 efficiently gives diene 29 which undergoes selective hydroboration/oxidation to afford nanaimoal.
• Synthesis of (±)-Nanaimoal and (±)-Nanaimool from<i>N,N</i>-Diethylgeranylamine
  作者：Takashi Yamada、Kunihiko Takabe

  DOI：10.1246/cl.1993.29

  日期：1993.1

  (±)-Nanaimoal and (±)-nanaimool were synthesized via Diels-Alder Reaction of 1,1-dimethyl-2,3-dimethylenecyclohexane, a novel building block for cyclic terpenoids, easily prepared from N,N-diethylgeranylamine.

  (±)-纳奈莫醇和(±)-纳奈莫醇是通过1,1-二甲基-2,3-二亚甲基环己烷的Diels-Alder反应合成的，这是一种新型的环状萜类化合物的构建块，易于从N,N-二乙基香叶胺制备。