2-(2,5,5-trimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)acetaldehyde | 146986-44-9

• 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)acetaldehyde
• 英文别名: (+/-)-nanaimoal；nanaimoal；2-(2,5,5-Trimethyl-1,3,4,6,7,8-hexahydronaphthalen-2-yl)acetaldehyde
• CAS: 146986-44-9
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: XOIZOXQRSWVEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 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)acetaldehyde 在 sodium tetrahydroborate 作用下， 以100%的产率得到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
• 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 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)acetaldehyde
  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

• A modified Robinson annulation process to α,α-disubstituted-β,γ-unsaturated cyclohexanone system. Application to the total synthesis of nanaimoal
  作者：Hsing-Jang Liu、Tai Wei Ly、Chia-Liang Tai、Jen-Dar Wu、Jinn-Kwei Liang、Jiunn-Cheh Guo、Nai-Wen Tseng、Kak-Shan Shia

  DOI：10.1016/s0040-4020(03)00034-6

  日期：2003.2

  reactions, giving the corresponding 2,2-disubstituted-3-cyclohexenone derivatives in a completely regioselective manner. This newly developed methodology has been successfully applied towards the total synthesis, in racemic form, of the marine natural product nanaimoal.

  发现4-氰基-2-环己烯酮易于还原烷基化反应，以完全区域选择性的方式得到相应的2，2-二取代-3-环己烯酮衍生物。这种新开发的方法已成功地以消旋形式完全合成了海洋天然产物纳那莫尔。
• Reductive Alkylation of γ-Cyano-α,β-unsaturated Ketones. A Modified Robinson Annulation Process to α,α-Disubstituted β,γ-unsaturated Cyclohexanone System
  作者：Chia-Liang Tai、Tai Wei Ly、Jen-Dar Wu、Kak-Shan Shia、Hsiang-Jang Liu

  DOI：10.1055/s-2001-10788

  日期：——

  Reductive alkylation of various 4-cyano-2-cyclohexenones, readily available from α-cyano ketones via a Robinson annulation process, gave rise to the corresponding 2,2-disubstituted-3-cyclohexenone derivatives in a completely regioselective manner. Application of this methodology resulted in an efficient synthesis of the marine natural product nanaimoal in racemic form.

  各种4-氰基-2-环己烯酮的还原烷基化，很容易通过罗宾逊成环过程从α-氰基酮获得，以完全区域选择性的方式产生相应的2,2-二取代-3-环己烯酮衍生物。该方法的应用导致了外消旋形式的海洋天然产物 nanaimoal 的有效合成。
• 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.
• 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.
• 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。