hepta-2,6-dienoic acid methyl ester | 25172-07-0

• 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: hepta-2,6-dienoic acid methyl ester
• 英文别名: methyl (Z)-2,6-heptadienoate；Methyl-cis-hepta-2,6-dienoat；methyl (2Z)-hepta-2,6-dienoate
• CAS: 25172-07-0
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: GHDDNOPAVQADSN-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：

  hepta-2,6-dienoic acid methyl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 (2Z)-2,6-heptadien-1-ol
  参考文献：
  名称：

  二氧化硫自由基[ n +1]环

  摘要：

  提出了一种使用二氧化硫作为双基自由基受体/供体的[ n +1]自由基环化的新方法。这种方法学为在非常温和的条件下利用自由基链机理形成五元，六元和七元环状砜提供了一条新颖的途径。

  DOI：

  10.1021/jo052035t
• 作为产物：
  描述：

  4-戊烯醛 在 甲醇 、 sodium 作用下， 以 丙酮 为溶剂， 生成 hepta-2,6-dienoic acid methyl ester
  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 Syntheses of (−)-Grandinolide and (−)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyltrans-3-Pentenoate: Elucidation of the Stereostructure of (−)-Sapranthin
  作者：Christian Harcken、Reinhard Brückner、Elisabeth Rank

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2342::aid-chem2342>3.0.co;2-q

  日期：1998.11.2

  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.
• Radical [<i>n</i> + 1] Annulations with Sulfur Dioxide
  作者：Anna Tsimelzon、Rebecca Braslau

  DOI：10.1021/jo052035t

  日期：2005.12.1

  A new methodology for [n + 1] radical annulation using sulfur dioxide as a geminal radical acceptor/donor is presented. This methodology provides a novel route to the formation of five-, six-, and seven-membered cyclic sulfones utilizing a radical chain mechanism under very mild conditions.

  提出了一种使用二氧化硫作为双基自由基受体/供体的[ n +1]自由基环化的新方法。这种方法学为在非常温和的条件下利用自由基链机理形成五元，六元和七元环状砜提供了一条新颖的途径。
• Photochemistry of some carbonyl-conjugated 1,5-hexadienes
  作者：Jack K. Crandall、Charles F. Mayer

  DOI：10.1021/jo00834a040

  日期：1970.9