(4S,8S)-(+)-4,8-trimethyldecanal | 85880-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,8S)-(+)-4,8-trimethyldecanal
• 英文别名: (4S,8S)-(+)-4,8-dimethyldecanal；(S,S)-(+)-4,8-dimethyldecanal；(4S,8S)-4,8-dimethyldecanal；4,8-dimethyldecanal；(4S,8S)-tribolure；(S,s)-4,8-di-methyldecanal
• CAS: 85880-36-0
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: XAUQKOJHYTYNRM-RYUDHWBXSA-N

物化性质

• 沸点：
  85 °C(Press: 7 Torr)
• 密度：
  0.820±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (4S,8S)-(+)-4,8-trimethyldecanal 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 (4S,8S)-4,8-dimethyl-1-decanol
  参考文献：
  名称：

  Pheromone synthesis. Part 245: Synthesis and chromatographic analysis of the four stereoisomers of 4,8-dimethyldecanal, the male aggregation pheromone of the red flour beetle, Tribolium castaneum

  摘要：

  All four stereoisomers of 4,8-dimethyldecanal (1) were synthesized from the enantiomers of 2-methyl-1-butanol and citronellal. Enantioselective GC analysis enabled separation of (4R,8R)-1 and (4R,8S)-1 from a mixture of (45,8R)-1 and (4S,8S)-1, when octakis-(2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin was employed as a chiral stationary phase. Complete separation of the four stereoisomers of 1 on reversed-phase HPLC at -54 degrees C was achieved after oxidation of 1 to the corresponding carboxylic acid 12 followed by its derivatization with (1R,2R)-2-(2,3-anthracenedicarboximido) cyclohexanol, and the natural 1 was found to be a mixture of all the four stereoisomers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.086
• 作为产物：
  描述：

  (R)-(+)-6,6-dimethoxy-3-methylhexyl phenyl sulfone 在 正丁基锂 、 高氯酸 、 lithium ethylamide 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 (4S,8S)-(+)-4,8-trimethyldecanal
  参考文献：
  名称：

  Mori, Kenji; Takikawa, Hirosato, Liebigs Annalen der Chemie, 1991, # 5, p. 497 - 500

  摘要：

  DOI：

文献信息

• Synthesis of all of the four possible stereoisomers of 4,8-dimethyldecanal, the aggregation pheromone of the flour beetles
  作者：Kenji Mori、Shigefumi Kuwahara、Hiraki Ueda

  DOI：10.1016/s0040-4020(01)91971-4

  日期：1983.1
• Odinokov, V. N.; Akhmetova, V. R.; Khasanov, Kh. D., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.1, p. 915 - 918
  作者：Odinokov, V. N.、Akhmetova, V. R.、Khasanov, Kh. D.、Abduvakhabov, A. A.、Sul'tanmuratova, V. R.、Tolsikov, G. A.

  DOI：——

  日期：——
• Terpenes in organic synthesis
  作者：G. D. Gamalevich、B. N. Morozov、E. P. Serebryakov

  DOI：10.1007/bf01433762

  日期：1996.1

  All four stereoisomers of 2,6-dimethyloctan-1-ol, the nearest precursors of the title formates, were synthesized in five to eight stages, with configurational purity ranging from 41 to 96 %, employing a stereodivergent scheme based on the partial hydrolysis of two pseudoracemic substrates, (2RS,6R)-2,6-dimethyloct-1-yl formate and (2RS,6S)-2,6-dimethyloct-1-yl acetate, in the presence of porcine pancreatic lipase (PPL). Configurations and diastereomeric compositions of the alcohols thus obtained were determined by correlating the latter with (S,S)-4,8-dimethyldecanal, prepared on the basis of enantioselective biohydrogenation of (R)-2,6-dimethylocta-2,7-dienal with bakers' yeast, and by comparing the [alpha](D) values of the alcohols with their NMR data and/or with those of their (S)-MTPA derivatives. The attractant potency of stereoisomeric 2,6-dimethyloct-1-yl formates towards Tribolium confusum was found to vary depending on their diastereomeric composition. The configuration at C(6) exerts some influence on the stereoselectivity of the PPL-catalyzed hydrolysis of pseudoracemic 2,6-dimethyloct-1-yl formates.
• Suzuki, Takahisa; Ozaki, Jotaro; Sugawara, Ryozo, Agricultural and Biological Chemistry, 1983, vol. 47, # 4, p. 869 - 876
  作者：Suzuki, Takahisa、Ozaki, Jotaro、Sugawara, Ryozo

  DOI：——

  日期：——
• AXMETOVA, V. R.;XASANOV, X. D.;ODINOKOV, V. N.;TOLSTIKOV, G. A., 9 SOV.-IND. SIMP. PO XIMII PRIROD. SOED., RIGA, 15-18 MAYA, 1989, RIGA,(1+
  作者：AXMETOVA, V. R.、XASANOV, X. D.、ODINOKOV, V. N.、TOLSTIKOV, G. A.

  DOI：——

  日期：——