(2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate | 872326-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate
• 英文别名: (3Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate；ethyl (2Z,4E)-6-phenylmethoxyhexa-2,4-dienoate
• CAS: 872326-43-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: RVIPXWGIPRSLHV-HYPVGTFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate 在 Hydroquinone 1,4-phthalazinediyl diether 、 甲基磺酰胺 四氧化锇 、 camphor-10-sulfonic acid 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 15.0h， 生成 (3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one
  参考文献：
  名称：

  De Novo Asymmetric Syntheses of d- and l-Talose via an Iterative Dihydroxylation of Dienoates

  摘要：

  A short and highly efficient route to D- and L-talo-gamma-lactones has been developed. The key transformation was the sequential osmium-catalyzed bis-dihydroxylation reaction of substituted 2,4-dienoates. When the first dihydroxylation reaction is performed on (2Z,4E)-dienoates with use of the Sharpless AD-mix procedure, a regio- and enantioselective dihydroxylation resulted along with an in situ lactonization. A subsequent dihydroxylation, using OsO4/NMO in MeOH conditions, resulted in an exceedingly diastereo- and enantioselective synthesis of talo-gamma-lactone.

  DOI：

  10.1021/jo051476+
• 作为产物：
  描述：

  (E)-4-benzyloxy-2-butenal 、 乙基[二(2,2,2-三氟乙氧基)氧膦基]乙酸 在 18-冠醚-6 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 (2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate 、 (2E,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate
  参考文献：
  名称：

  De Novo Asymmetric Syntheses of d- and l-Talose via an Iterative Dihydroxylation of Dienoates

  摘要：

  A short and highly efficient route to D- and L-talo-gamma-lactones has been developed. The key transformation was the sequential osmium-catalyzed bis-dihydroxylation reaction of substituted 2,4-dienoates. When the first dihydroxylation reaction is performed on (2Z,4E)-dienoates with use of the Sharpless AD-mix procedure, a regio- and enantioselective dihydroxylation resulted along with an in situ lactonization. A subsequent dihydroxylation, using OsO4/NMO in MeOH conditions, resulted in an exceedingly diastereo- and enantioselective synthesis of talo-gamma-lactone.

  DOI：

  10.1021/jo051476+

文献信息

• Ahmed, Md. Moinuddin; Akhmedov, Novruz G.; Cui, Hu, Heterocycles, 2006, vol. 70, p. 223 - 233
  作者：Ahmed, Md. Moinuddin、Akhmedov, Novruz G.、Cui, Hu、Friedrich, Dirk、O'Doherty, George A.

  DOI：——

  日期：——
• De Novo Asymmetric Syntheses of <scp>d</scp>- and <scp>l</scp>-Talose via an Iterative Dihydroxylation of Dienoates
  作者：Md. Moinuddin Ahmed、George A. O'Doherty

  DOI：10.1021/jo051476+

  日期：2005.12.1

  A short and highly efficient route to D- and L-talo-gamma-lactones has been developed. The key transformation was the sequential osmium-catalyzed bis-dihydroxylation reaction of substituted 2,4-dienoates. When the first dihydroxylation reaction is performed on (2Z,4E)-dienoates with use of the Sharpless AD-mix procedure, a regio- and enantioselective dihydroxylation resulted along with an in situ lactonization. A subsequent dihydroxylation, using OsO4/NMO in MeOH conditions, resulted in an exceedingly diastereo- and enantioselective synthesis of talo-gamma-lactone.