(2R,3R,4R,8R,E)-8-(acryloyloxy)undeca-6,10-diene-2,3,4-tri-O-acetate | 1439364-97-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R,4R,8R,E)-8-(acryloyloxy)undeca-6,10-diene-2,3,4-tri-O-acetate
• 英文别名: [(4R,5E,8R,9R,10R)-8,9,10-triacetyloxyundeca-1,5-dien-4-yl] prop-2-enoate
• CAS: 1439364-97-2
• 化学式: C₂₀H₂₈O₈
• 分子量: 396.438
• InChiKey: MHKPTQCAGHEVBR-XLBJJTSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,8R,E)-8-(acryloyloxy)undeca-6,10-diene-2,3,4-tri-O-acetate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到synargentolide A
  参考文献：
  名称：

  Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

  摘要：

  Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an alpha,alpha'-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee > 99%). After the asymmetric synthesis of the triol fragment of the molecule, the delta-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.

  DOI：

  10.1055/s-0032-1316865
• 作为产物：
  描述：

  (2R,3R,4R)-hept-6-ene-2,3,4-tri-O-acetate 在 Hoveyda-Grubbs catalyst second generation 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 50.5h， 生成 (2R,3R,4R,8R,E)-8-(acryloyloxy)undeca-6,10-diene-2,3,4-tri-O-acetate
  参考文献：
  名称：

  Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

  摘要：

  Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an alpha,alpha'-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee > 99%). After the asymmetric synthesis of the triol fragment of the molecule, the delta-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.

  DOI：

  10.1055/s-0032-1316865

文献信息

• Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology
  作者：Dieter Enders、Linus Reichenbach

  DOI：10.1055/s-0032-1316865

  日期：——

  Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an alpha,alpha'-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee > 99%). After the asymmetric synthesis of the triol fragment of the molecule, the delta-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.