(8aR)-albicanal | 293309-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (8aR)-albicanal
• 英文别名: (+)-albicanal；(+)-arbicanal；(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalene-1-carbaldehyde
• CAS: 293309-97-4
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: CYNSNODFYUHSCP-NFAWXSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 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：

  (8aR)-albicanal 在 仲丁基锂 、 lithium 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 、 氨 为溶剂， 反应 0.33h， 生成 (+)-zonarol dimethyl ether
  参考文献：
  名称：

  Total synthesis of yahazunol, zonarone and isozonarone

  摘要：

  The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00346-0
• 作为产物：
  描述：

  (1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl-methanol 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (8aR)-albicanal
  参考文献：
  名称：

  新型鞘氨醇激酶抑制剂（-）-F-12509A的合成及其绝对构型的确定

  摘要：

  新型鞘氨醇激酶抑制剂（-）-F-12509A（（-）- 1）的合成以高效的方式完成，该方法包括九个最长的线性步骤，且从（-）-双环β-的总收率达45％酮酸酯（-）- 2，其绝对构型确定为（5 S，9 S，10 S）。

  DOI：

  10.1016/j.tetlet.2007.05.043

文献信息

• Total synthesis of the marine sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone
  作者：Jörg Schröder、Christine Magg、Karlheinz Seifert

  DOI：10.1016/s0040-4039(00)00891-1

  日期：2000.7

  The total synthesis of the naturally occurring sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone was achieved starting from β-ionone, which was transformed via (+)-albicanic acid to (+)-albicanal and (−)-drim-7-en-11-al. Coupling of the aldehydes with lithiated hydroquinone ethers and further modification of the coupling products led to the target

  天然倍半萜烯对苯二酚唑纳洛尔和异唑烷酮以及倍半萜烯醌佐那隆和异唑烷酮的全合成是从β-紫罗兰酮开始的，β-紫罗兰酮通过（+）-白蚁酸转化为（+）-白三醛和（-）-drim- 7-en-11-al。醛与锂化对苯二酚醚的偶联以及偶联产物的进一步修饰产生了目标分子。
• Total Synthesis of the Marine Sesquiterpene Quinones Hyatellaquinone and Spongiaquinone
  作者：Andreas Bernet、Jörg Schröder、Karlheinz Seifert

  DOI：10.1002/hlca.200390158

  日期：2003.6

  The synthesis of the marine sesquiterpene quinone (+)-hyatellaquinone (1) was achieved starting from the sesquiterpene aldehyde (+)-albicanal ((+)-3) (Schemes 3 and 4). Coupling of (+)-albicanal with 2,3,5,6-tetramethoxyphenyllithium led to the aryl-sesquiterpene system, which was modified to the target molecule. Furthermore, the first total synthesis of the marine compound spongiaquinone (2) was carried

  从倍半萜醛（+）-白色醛（（+）- 3）（方案3和4）开始，实现了海洋倍半萜烯醌（+）-杂萘醌（1）的合成。（+）-白色醛与2,3,5,6-四甲氧基苯基锂的偶联导致芳基-倍半萜烯系统，该系统被修饰为目标分子。此外，海洋化合物海绵醌（2）的第一个全合成是从（（-）-白色（3）-3）开始的，其反应顺序包括立体选择性CC键加氢和一锅AcOH消除/去甲基化反应（方案7和10）。1和2的1,2-和1,4-苯醌形式的出现取决于溶剂系统的pH值。
• Determination of the absolute structure of albaconol
  作者：Mikio Fujii、Sadayuki Ishii、Ryota Saito、Hiroyuki Akita

  DOI：10.1016/j.tet.2008.03.050

  日期：2008.5

  The concise synthesis of (8aR)-(-)-albaconol (1) from (8aR)-albicanol (2) obtained from the lipase-assisted asymmetric acetylation of rac-2, was achieved in 45% overall yield (eight steps). By comparison of the sign of specific rotation of between synthetic (8aR)-(-)-albaconol (1) and natural (+)-albaconol (1), the absolute structure of natural (+)-1 was determined to be 1R,2R,4aS,8aS configuration. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of a novel sphingosine kinase inhibitor (−)-F-12509A and determination of its absolute configuration
  作者：Nobuhiro Maezawa、Noriyuki Furuichi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1016/j.tetlet.2007.05.043

  日期：2007.7

  The synthesis of a novel sphingosine kinase inhibitor, (−)-F-12509A ((−)-1), was achieved in a highly efficient manner that included nine longest linear steps and 45% overall yield from (−)-bicyclic β-ketoester (−)-2, and its absolute configuration was determined to be (5S,9S,10S).

  新型鞘氨醇激酶抑制剂（-）-F-12509A（（-）- 1）的合成以高效的方式完成，该方法包括九个最长的线性步骤，且从（-）-双环β-的总收率达45％酮酸酯（-）- 2，其绝对构型确定为（5 S，9 S，10 S）。
• Total synthesis of yahazunol, zonarone and isozonarone
  作者：Thorsten Laube、Jörg Schröder、Ralf Stehle、Karlheinz Seifert

  DOI：10.1016/s0040-4020(02)00346-0

  日期：2002.5

  The synthesis of the marine natural products zonarone and isozonarone was achieved via (+)-albicanic acid, a sesquiterpene of the drimane type. Coupling of the appropiate drimane-synthon with lithiated hydroquinone ethers led to sesquiterpene arenes, which were further modified to the target molecules. Stereoselective epoxidation followed by regioselective opening of the oxirane ring yielded yahazunol. (C) 2002 Elsevier Science Ltd. All rights reserved.