(S)-(+)-1-methyldodecyl acetate | 120876-13-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-(+)-1-methyldodecyl acetate
• 英文别名: (S)-(+)-2-Tridecanol Acetate；(S)-2-tridecanol acetate；(S)-2-tridecanyl acetate；(S)-tridec-2-yl acetate；(S)-2-acetoxytridecane；(S)-2-tridecyl acetate；[(2S)-tridecan-2-yl] acetate
• CAS: 120876-13-3
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: ZJSXXRKLMXNOCL-AWEZNQCLSA-N

物化性质

• 沸点：
  281.3±8.0 °C(Predicted)
• 密度：
  0.865±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-1-(2-nonyl-1,3-dithian-2-yl)-2-propyl acetate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以82%的产率得到(S)-(+)-1-methyldodecyl acetate
  参考文献：
  名称：

  Bracher, Franz; Schulte, Brigitte, Organic Preparations and Procedures International, 1995, vol. 27, # 6, p. 682 - 684

  摘要：

  DOI：

文献信息

• Synthesis of derivatives of (S)-2-alkanols, components of pheromones ofDrosophila mulleri andRhyzopertha dominica, from (S)-(+)-3,7-dimethylocta-1,6-diene
  作者：G. Yu. Ishmuratov、R. Ya. Kharisov、O. V. Botsman、V. V. Zorin、G. A. Tolstikov

  DOI：10.1007/bf02494932

  日期：2000.11

  Effective routes for the synthesis of (S)-2-acetoxytridecane, the sex pheromone of the fruit flyDrosophila mulleri, and (S)-1-methylbutyl 2-methyl- and 2,4-dimethylpent-2E-enoates, components of the aggregation pheromone of the lesser grain borerRhyzopertha dominica, were developed on the basis of (S)-4-methylhex-5-en-1-yl tosylate accessible from (S)-(+)-dihydromyreene.

  合成 (S)-2-乙酰氧基十三烷、果蝇的性信息素和 (S)-1-甲基丁基 2-甲基-和 2,4-二甲基戊-2E-烯酸酯、聚合组分的有效途径小粒螟的信息素是基于可从 (S)-(+)-dihydromyreene 获得的 (S)-4-methylhex-5-en-1-yl tosylate 开发的。
• Enantioselective Bioreduction of 5-Hexen-2-one in Directional Synthesis of Insect Pheromones
  作者：N. I. Petukhova、V. V. Zorin、A. R. Sakaeva、A. V. Mityagina、E. R. Nurieva、V. A. Vydrina、M. P. Yakovleva、G. Yu. Ishmuratov

  DOI：10.1134/s1070427222030156

  日期：2022.3

  acetate in 58% yield by dilithium tetrachlorocuprate catalyzed cross-coupling with the Grignard reagent derived from n-octyl bromide; and reduction of both ester groups in the tosylate with lithium aluminum hydride to (S)-pentan-2-ol (yield 79%), followed by its esterification with (2Е)-2-methylpent-2-enoyl or (2Е)-2,4-dimethylpent-2-enoyl chloride with 68 and 69% yields, respectively.

  摘要 (2 S )-十三烷基乙酸酯（果蝇的性信息素）和 (2 Е )-2-methylpent-2-enoic 和 (2 Е )-2,4-dimethylpent-2-的( S )-1-甲基丁酯烯酸（Rhyzopertha dominica小螟虫的聚集信息素的成分）由市售的 5-hexen-2-one（烯丙基丙酮）合成，基于起始酮的总产率分别为 31.0、28.8 和 29.2%。该过程的关键步骤是 5-hexen-2-one 与Rhodococcus erythropolis А-25 放线菌的对映选择性生物还原为 ( S )-5-hexen-2-ol，产率为 77% ( ее98.4%) 和以下化学选择性反应：( S )-5-hexen-2-yl acetate 的臭氧裂解，然后在 88 中用 NaBH 4将过氧产物还原为 ( S )-5-hydroxypent-2-yl acetate
• Studies on PPL Catalyzed Acetylation of 2-Alkanols: Its Application for the Synthesis of 2-Dodecanol and 2-Tridecyl Acetate, the Pheromones of<i>Crematogaster</i>Ants and<i>Drosophila mulleri</i>Flies
  作者：Anubha Sharma、Archana S. Pawar、Subrata Chattopadhyay

  DOI：10.1080/00397919608003858

  日期：1996.1

  Several aliphatic 2-alkanols with varying chain length has been efficiently resolved by their acetylation using vinyl acetate/PPL in diisopropyl ether. The effect of solvent polarity, position and type of unsaturation and chain length has been probed. This has led to more convenient synthesis of some insect pheromones.
• Insect pheromones and their analogs. LX. Stereocontrolled synthesis of sex pheromones ofDrosophila mulleri andMayetiola destructor
  作者：R. Ya. Kharisov、N. I. Petukhova、A. R. Davletova、N. M. Ishmuratova、V. V. Zorin、G. Yu. Ishmuratov、G. A. Tolstikov

  DOI：10.1007/bf02236433

  日期：2000.3

  Syntheses are developed for 2S-tridecyl- and 2S-tridec-10E-enylacetates, sex pheromones of the fruit fly Drosophila mulleri and the Hessian fly Mayetiola destructor, respectively, that are based on ethyl-3S-hydroxybutanoate, a product from enzymatic reduction of ethyl acetoacetate by the soil yeast strain "80-1."
• Enders, Dieter; Plant, Andrew, Liebigs Annalen der Chemie, 1991, # 11, p. 1241 - 1243
  作者：Enders, Dieter、Plant, Andrew

  DOI：——

  日期：——