methyl (2-ethenyl-4-pentenoate) | 922-00-9

• 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: methyl (2-ethenyl-4-pentenoate)
• 英文别名: methyl-2-ethylenyl-4-pentenoate；methyl 2-ethenyl-4-pentenoate；methyl 2-vinyl-4-pentenoate；Allyl-vinyl-essigsaeure-methylester；2-Vinyl-4-pentensaeure-methylester；Methyl-2-vinyl-4-pentenoat；4-Pentenoic acid, 2-ethenyl-, methyl ester；methyl 2-ethenylpent-4-enoate
• CAS: 922-00-9
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: UUOPYQZJWLRMPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (2-ethenyl-4-pentenoate) 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 1,2,2,6,6-五甲基哌啶 、 copper(l) iodide 、 草酰氯 、 四丁基氟化铵 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 lithium iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 44.08h， 生成 (E)-11,15-hexadecadiene-7,9-diyn-1-ol
  参考文献：
  名称：

  Total Syntheses of (−)-Grandinolide and (−)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyltrans-3-Pentenoate: Elucidation of the Stereostructure of (−)-Sapranthin

  摘要：

  Methyl trans-3-pentenoate (7) was converted into the cis-substituted gamma-lactone 8 in a single step with 78 % ee. The derived enolate dilithio-8 was alkylated trans-selectively with primary iodoalkanes. with 1-iodobutane dilithio-8 afforded, after esterification with isovaleroyl chloride, the epi-blast mycinone 9, Dilithio-8 gave (-)-grandinolide (11) with 1-iodo-19-phenylnonadecane (20), A third trans-selective alkylation of dilithio-8 was undertaken with 16-iodo-1.5-hexadecadiene-7,9-diyne (21). This gave the gamma-lactone 12. which had the published relative configuration of (-)-sapranthin but different spectroscopic data, When the OH group of lactone 8 was inverted (to hydroxylactone 40) and the derived enolate dilithio-40 alkylated with iodide 21, lactone 41 resulted, Its H-1 and C-13 NMR spectra and the sign and value of optical rotation coincide with the data of natural sapranthin, These findings establish that (-)-sapranthin possesses the relative and absolute configuration of stereoformula 41. The synthesis of iodide 21 was performed via the dienoic carboxylic ester trans-23 which stemmed from the Claisen-Ireland rearrangement (27 --> 28/29)/esterification (28/29 --> 26)/Cope rearrangement (26 - 23) sequence shown in Scheme 5.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2342::aid-chem2342>3.0.co;2-q
• 作为产物：
  描述：

  4-戊烯醛 、 diethyl methoxycarbonylmethylphosphonate 生成 methyl (2-ethenyl-4-pentenoate)
  参考文献：
  名称：

  Photochemistry of some carbonyl-conjugated 1,5-hexadienes

  摘要：

  DOI：

  10.1021/jo00834a040

文献信息

• Total synthesis of vineomycinone B2 methyl ester
  作者：Samuel Danishefsky、Biing Jiun Uang、George Quallich

  DOI：10.1021/ja00291a031

  日期：1985.3

  Synthese faisant intervenir des siloxy dienes avec deux reactions homo-Diels Alder et une reaction hetero-Diels Alder

  合成这些 faisant intervenir des siloxy diene avec deux 反应 homo-Diels Alder et une 反应hetero-Diels Alder
• Total synthesis of vineomycin B2 aglycon
  作者：Samuel Danishefsky、Biing Jiun Uang、George Quallich

  DOI：10.1021/ja00320a049

  日期：1984.4

  Synthese du compose du titre qui est l'acide dihydroxy-1,5 [dihydroxy-4,5 methyl-6 perhydropyrannyl-2]-6 β-hydroxy β-methyl anthraquinonebutyrique-2

  Synthese du compose du titre qui est l'acide dihydroxy-1,5 [dihydroxy-4,5methyl-6 perhydropyrannyl-2]-6 β-hydroxy β-methyl anthraquinonebutyrique-2
• Selective .gamma. alkylation of dienolate anions derived from .alpha.,.beta.-unsaturated acids. Applications to the synthesis of isoprenoid olefins
  作者：John A. Katzenellenbogen、Ann L. Crumrine

  DOI：10.1021/ja00432a038

  日期：1976.8
• Calo, Vincenzo; Lopez, Luigi; Pesce, Giannangelo, Gazzetta Chimica Italiana, 1990, vol. 120, # 3, p. 203 - 205
  作者：Calo, Vincenzo、Lopez, Luigi、Pesce, Giannangelo

  DOI：——

  日期：——
• CALO, VINCENZO;LOPEZ, LUIGI;PESCE, GIANNANGELO, GAZZ. CHIM. ITAL., 120,(1990) N, C. 203-205
  作者：CALO, VINCENZO、LOPEZ, LUIGI、PESCE, GIANNANGELO

  DOI：——

  日期：——