(E)-N-methoxy-N-methyl-5-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)pent-2-enamide | 1192591-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-N-methoxy-N-methyl-5-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)pent-2-enamide
• 英文别名: (E)-5-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methoxy-N-methylpent-2-enamide
• CAS: 1192591-81-3
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: SZKAMWDWSVLBLT-RIYCMIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N-methoxy-N-methyl-5-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)pent-2-enamide 、 2,2-dimethyl-6-(2-oxopropyl)-4H-1,3-dioxin-4-one 在 lithium diisopropyl amide 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以18%的产率得到6-((2Z,5E)-2-hydroxy-8-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-4-oxoocta-2,5-dienyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence

  摘要：

  The total synthesis of aigialomycin D, without the need for phenol protection, was carried out using the C-acylation of a keto-dioxinone dianion, a cascade sequence consisting of ketene generation, alcohol trapping and aromatization, and ring-closing metathesis.

  DOI：

  10.1021/ol901979x
• 作为产物：
  描述：

  3-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanal 、 N-甲氧基-N-甲基-2-(三苯基磷)乙酰胺N-甲氧基-N-甲基-2-(三苯基磷)乙酰胺 以 二氯甲烷 为溶剂， 反应 14.0h， 以13 mg的产率得到(Z)-N-methoxy-N-methyl-5-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)pent-2-enamide
  参考文献：
  名称：

  Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence

  摘要：

  The total synthesis of aigialomycin D, without the need for phenol protection, was carried out using the C-acylation of a keto-dioxinone dianion, a cascade sequence consisting of ketene generation, alcohol trapping and aromatization, and ring-closing metathesis.

  DOI：

  10.1021/ol901979x

文献信息

• Total Synthesis of Aigialomycin D using a One-Pot Ketene Generation−Trapping−Aromatization Sequence
  作者：Frederick Calo、Jeffery Richardson、Anthony G. M. Barrett

  DOI：10.1021/ol901979x

  日期：2009.11.5

  The total synthesis of aigialomycin D, without the need for phenol protection, was carried out using the C-acylation of a keto-dioxinone dianion, a cascade sequence consisting of ketene generation, alcohol trapping and aromatization, and ring-closing metathesis.