(+)-(1S)-1-methylbutyl (2E)-2-methylpent-2-enoate | 80510-15-2

• 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: (+)-(1S)-1-methylbutyl (2E)-2-methylpent-2-enoate
• 英文别名: (E)-(S)-(+)-1-methylbutyl 2-methyl-2-pentenoate；(S)-(+)-1-Methylbutyl (E)-2-methyl-2-pentenoate；(S)-(+)-2'-pentyl (E)-2-methyl-2-pentenoate；(S)-1-methylbutyl (E)-2-methyl-2-pentenoate；(S)-1-methylbutyl 2-methylpent-2E-enoate；(S)-dominicalure 1；Dominicalure I；[(2S)-pentan-2-yl] (E)-2-methylpent-2-enoate
• CAS: 80510-15-2
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: HPKANHQEOBMBEF-PCYYEKQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  2-戊醇 在 草酰氯 作用下， 以 乙醚 为溶剂， 反应 68.25h， 生成 (+)-(1S)-1-methylbutyl (2E)-2-methylpent-2-enoate
  参考文献：
  名称：

  Enzyme reactions in apolar solvent. 5. The effect of adjacent unsaturation on the porcine pancreatic lipase catalyzed kinetic resolution of secondary alcohols

  摘要：

  The effect of adjacent unsaturation on the enzyme-catalyzed kinetic resolution of secondary alcohols is studied for a series of allylic, homoallylic, propargylic, homopropargylic, and phenyl-substituted 2-alkanols, using porcine pancreatic lipase (PPL) in anhydrous Et2O. Excellent enantioselectivity (high E value) was observed for alpha-phenethyl alcohol (3), propargylic alcohols (8 and 11), and (E)-allylic alcohols (9 and 12), but (Z)-allylic alcohols (10 and 13) showed poor selectivity. Enantioselectivity was also low for both (E)- and (Z)-homoallylic alcohols (15 and 16), homopropargylic alcohol (14), I-phenyl-2-propanol (6), and 4-phenyl-2-butanol (7). The enhanced enantioselectivity observed for (E)-allylic alcohols was exploited in the synthesis of the enantiomers of both components of the aggregation pheromone of the lesser grain borer, Rhyzopertha dominica (F.). The magnitude of the enantiomeric ratio (E value) can be dramatically affected by the accuracy of the values of ee(s) and ee(p) used in the calculation, especially when E is large. Variation in the value of E with the optical purity of the chiral derivatizing agent used to determine ee(s) and ee(p) is illustrated.

  DOI：

  10.1021/jo00037a049

文献信息

• Stereoselective synthesis of dominicalure 1 and 2: Components of aggregation pheromone from male lesser grain borerRhyzopertha dominica (F.)
  作者：J. Razkin、P. Gil、A. Gonzalez

  DOI：10.1007/bf02033577

  日期：1996.4

  Dominicalure 1 (9a) and dominicalure 2 (9b), were synthesized by esterification of alpha,beta-unsaturated acids4a and4b with (S)-(+)-2-pentanol (8). The key step was the asymmetric reduction of 3-penten-2-one (5) to give the chiral intermediate6, which, upon diimide reduction, DNB derivatization, recrystallization, and hydrolysis, yielded8 in 63% ee. Acids4a and4b were prepared in a simple and efficient

  Dominicalure 1 (9a) 和 dominicalure 2 (9b) 是通过 α,β-不饱和酸 4a 和 4b 与 (S)-(+)-2-戊醇 (8) 酯化合成的。关键步骤是 3-penten-2-one (5) 的不对称还原得到手性中间体 6，在二酰亚胺还原、DNB 衍生化、重结晶和水解后，得到 63% ee 的 8。酸 4a 和 4b 以简单有效的三步合成法制备，总收率分别为 54% 和 62%，呈立体异构纯形式。
• 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。
• A Facile Zn-mediated Stereoselective Synthesis of (<i>E</i>)- and (<i>Z</i>)-Trisubstituted Alkenes from Baylis–Hillman Adducts in Water and Its Application
  作者：Biswanath Das、Nikhil Chowdhury、Joydeep Banerjee、Anjoy Majhi、Gurram Mahender

  DOI：10.1246/cl.2006.358

  日期：2006.4

  A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis-Hillman adducts with Zn in saturated aq. NH 4 Cl solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer Rhyzopertha dominica

  通过用饱和水溶液中的 Zn 处理 Baylis-Hillman 加合物的乙酰衍生物，已经完成了 (E)- 和 (Z)- 三取代烯烃的简单有效的立体选择性合成。NH 4 Cl 溶液回流。该方法已用于制备小螟Rhyzopertha dominica (F) 的两种手性昆虫信息素 dominicalure-I 和 dominicalure-II。
• Synthetic Applications of theBaylis–Hillman Reaction: Simple and Convenient Synthesis of Five Important Insect Pheromones
  作者：Biswanath Das、Joydeep Banerjee、Nikhil Chowdhury、Anjoy Majhi、Gurram Mahender

  DOI：10.1002/hlca.200690090

  日期：2006.5

  A simple and convenient synthesis of five important insect pheromones by means of Baylis–Hillman adducts is described, i.e., of (2E,4S)-2,4-dimethylhex-2-enoic acid (1), a mandibular-gland secretion of the male carpenter ant in the genus Camponotus, of (+)-(S)-manicone (2) and (+)-(S)-normanicone (3), two mandibular-gland constituents of Manica ants, and of (+)-dominicalure-I (6) and (+)-dominicalure-II

  描述了一种通过Baylis-Hillman加合物简单而方便地合成五个重要昆虫信息素的方法，即（2 E，4 S）-2,4-二甲基己二-2-烯酸（1），一种下颌腺分泌物Camponotus属中的雄性木匠蚂蚁，（+）-（S）-马尼康尼（2）和（+）-（S）-诺曼尼康尼（3），马尼卡蚂蚁的两个下颌腺成分和（+ ）-dominicalure-I（6）和（+）-dominicalure-II（7），小bore虫Rhyzopertha dominica的两个聚集信息素（F）。首次，将Baylis-Hillman化学方法用于立体选择性合成三取代烯烃的潜力成功地用于这些信息素化合物的合成。
• 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