(E)-(R)-(1)-1-methylbutyl 2-methyl-2-pentenoate | 140461-21-8

• 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: (E)-(R)-(1)-1-methylbutyl 2-methyl-2-pentenoate
• 英文别名: (R)-(-)-2'-pentyl (E)-2-methyl-2-pentenoate；(R)-1-Methylbutyl (E)-2-methyl-2-pentenoate；(R)-dominicalure 1；dominicalure II；[(2R)-pentan-2-yl] (E)-2-methylpent-2-enoate
• CAS: 140461-21-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: HPKANHQEOBMBEF-TTZKWOQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  草莓酸 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 3.5h， 生成 (E)-(R)-(1)-1-methylbutyl 2-methyl-2-pentenoate
  参考文献：
  名称：

  dominicalure 1 和 2 的立体选择性合成：来自雄性小粒螟Rhyzopertha dominica (F.) 的聚集信息素的成分。

  摘要：

  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。

  DOI：

  10.1007/bf02033577

文献信息

• Enzyme reactions in apolar solvent. 5. The effect of adjacent unsaturation on the porcine pancreatic lipase catalyzed kinetic resolution of secondary alcohols
  作者：Brian Morgan、Allan C. Oehlschlager、Thomas M. Stokes

  DOI：10.1021/jo00037a049

  日期：1992.5

  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.
• Green and Catalytic Synthesis of Dominicalure I, Major Component of the Aggregation Pheromone of <i>Rhyzopertha dominica</i> (Fabricius) (Coleoptera: Bostrichidae)
  作者：Estefanía Dibello、Gustavo Seoane、Daniela Gamenara

  DOI：10.1080/00397911.2014.997368

  日期：2015.4.18

  A new concise and efficient catalytic synthesis of dominicalure I, the male-produced aggregation pheromone of the grain borer Rhyzopertha dominica, is herein reported. The synthetic route was designed starting from easily available propanal through an organocatalytic key step and completed with biocatalytic procedures.
• Cheskis, B. A.; Shpiro, N. A.; Moiseenkov, A. M., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 9.1, p. 1613 - 1616
  作者：Cheskis, B. A.、Shpiro, N. A.、Moiseenkov, A. M.

  DOI：——

  日期：——
• CHESKIS, B. A.;SHPIRO, N. A.;MOISEENKOV, A. M., ZH. ORGAN. XIMII, 26,(1990) N, S. 1864-1869
  作者：CHESKIS, B. A.、SHPIRO, N. A.、MOISEENKOV, A. M.

  DOI：——

  日期：——
• CHESKIS, B. A.;SHPIRO, N. A., HOB. METODY I REAGENTY V TONK. ORGAN. SINTEZE: 5 BCEC. SIMP. PO ORGAN. SI+
  作者：CHESKIS, B. A.、SHPIRO, N. A.

  DOI：——

  日期：——