2-Methoxy-1,4-pentadien | 32520-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxy-1,4-pentadien
• 英文别名: 2-Methoxy-1,4-pentadiene；2-methoxypenta-1,4-diene
• CAS: 32520-60-8
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: JIMXMCFFUHMZBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  32-33 °C(Press: 75 Torr)
• 密度：
  0.791±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methoxy-1,4-pentadien 在 吡啶 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 12.0h， 生成 (4R)-2-(4-Hydroxy-4-methyl-5-((2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy)pentyl)-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  Nonracemic frontalin via copper- and palladium-based skeletal construction and the asymmetric dihydroxylation

  摘要：

  The new higher order organocuprate, Li2Cu(CN)(C(OMe):CH2)2, prepared through a Sn --> Li --> Cu transmetalation sequence, was found to efficiently couple with allyl bromide producing 2-methoxy-1,4-pentadiene (3) which is efficiently converted to the ketal 4. Hydroboration of 4 with 9-BBN-H and the selective oxidation of this adduct with trimethylamine N-oxide (TMANO) produces 9-oxa-10-borabicyclo[3.3.2]decane 5, which undergoes Pd-catalyzed cross coupling with 2-bromopropene producing 6, thereby accomplishing the construction of the frontalin carbon skeleton in 63% overall yield from allyl bromide. The Os-based dihydroxylation of 6 followed by ketalization either produces the racemic pheromone ((+/-)-1) or, with the Sharpless catalytic asymmetric dihydroxylation (dihydroquinine ligand) procedure, results in the selective formation of the S enantiomer in 35% ee. The de determined from the C-13 NMR spectra of the diastereomeric Mosher's monoesters (9) was found to provide useful corroborative information on the optical purity of the intermediate 1,2-diols 7.

  DOI：

  10.1021/jo00048a014
• 作为产物：
  描述：

  5-溴-4-甲氧基戊-1-烯 在 氢氧化钾 作用下， 以38%的产率得到2-Methoxy-1,4-pentadien
  参考文献：
  名称：

  Taskinen, Esko; Kuusisto, Merja, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 8, p. 571 - 574

  摘要：

  DOI：

文献信息

• Kirmse, Wolfgang; Rode, Klaus, Chemische Berichte, 1987, vol. 120, p. 839 - 846
  作者：Kirmse, Wolfgang、Rode, Klaus

  DOI：——

  日期：——
• A Convenient Synthesis of 2-Alkoxy-1,4-pentadienes from Unsymmetrical Allyldialkylboranes or Alkyldiallylboranes
  作者：Yu. N. Bubnov、M. Sh. Grigorian、A. V. Tsyban'、B. M. Mikhailov

  DOI：10.1055/s-1980-29262

  日期：——
• BUBNOV Y. N.; GRIGORIAN M. SH.; TSYBAN A. V.; MIKHAILOV B. M., SYNTHESIS, 1980, NO 11, 902-904
  作者：BUBNOV Y. N.、 GRIGORIAN M. SH.、 TSYBAN A. V.、 MIKHAILOV B. M.

  DOI：——

  日期：——
• KIRMSE, W.;RODE, K., CHEM. BER., 120,(1987) N 5, 839-846
  作者：KIRMSE, W.、RODE, K.

  DOI：——

  日期：——
• Nonracemic frontalin via copper- and palladium-based skeletal construction and the asymmetric dihydroxylation
  作者：Braulio Santiago、John A. Soderquist

  DOI：10.1021/jo00048a014

  日期：1992.10

  The new higher order organocuprate, Li2Cu(CN)(C(OMe):CH2)2, prepared through a Sn --> Li --> Cu transmetalation sequence, was found to efficiently couple with allyl bromide producing 2-methoxy-1,4-pentadiene (3) which is efficiently converted to the ketal 4. Hydroboration of 4 with 9-BBN-H and the selective oxidation of this adduct with trimethylamine N-oxide (TMANO) produces 9-oxa-10-borabicyclo[3.3.2]decane 5, which undergoes Pd-catalyzed cross coupling with 2-bromopropene producing 6, thereby accomplishing the construction of the frontalin carbon skeleton in 63% overall yield from allyl bromide. The Os-based dihydroxylation of 6 followed by ketalization either produces the racemic pheromone ((+/-)-1) or, with the Sharpless catalytic asymmetric dihydroxylation (dihydroquinine ligand) procedure, results in the selective formation of the S enantiomer in 35% ee. The de determined from the C-13 NMR spectra of the diastereomeric Mosher's monoesters (9) was found to provide useful corroborative information on the optical purity of the intermediate 1,2-diols 7.