(E)-(3R,6S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-hept-4-enoic acid dimethylamide | 162582-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(3R,6S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-hept-4-enoic acid dimethylamide
• 英文别名: (E,3R,6S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-hydroxy-N,N-dimethylhept-4-enamide
• CAS: 162582-71-0
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: JSDDBYUTSVKCOI-XRBRAWTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(3R,6S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-hept-4-enoic acid dimethylamide 在 potassium carbonate 、 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 反应 34.0h， 生成 (R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-((E)-propenyl)-dihydro-furan-2-one
  参考文献：
  名称：

  A 1,2-O-O-Silyl-Migration-Claisen-Rearrangement-Sn2'-Displacement Sequence in the Stereoselective Synthesis of 5-Oxaprostanoid Derivatives

  摘要：

  A novel stereocontrolled route to 5-oxaprostaglandin and PGF intermediates is described, which starts from the ene-diols (6/7) and uses a sequence of Claisen rearrangement, 1,2-O-O-silyl migration and S(N)2'-cyclization reactions (9b --> 10a/b via 11a/b).

  DOI：

  10.3987/com-94-s15
• 作为产物：
  描述：

  (E)-(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以97%的产率得到(E)-(3R,6S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-hept-4-enoic acid dimethylamide
  参考文献：
  名称：

  A 1,2-O-O-Silyl-Migration-Claisen-Rearrangement-Sn2'-Displacement Sequence in the Stereoselective Synthesis of 5-Oxaprostanoid Derivatives

  摘要：

  A novel stereocontrolled route to 5-oxaprostaglandin and PGF intermediates is described, which starts from the ene-diols (6/7) and uses a sequence of Claisen rearrangement, 1,2-O-O-silyl migration and S(N)2'-cyclization reactions (9b --> 10a/b via 11a/b).

  DOI：

  10.3987/com-94-s15

文献信息

• A 1,2-O-O-Silyl-Migration-Claisen-Rearrangement-Sn2'-Displacement Sequence in the Stereoselective Synthesis of 5-Oxaprostanoid Derivatives
  作者：Johann Mulzer、Stefan Greifenberg

  DOI：10.3987/com-94-s15

  日期：——

  A novel stereocontrolled route to 5-oxaprostaglandin and PGF intermediates is described, which starts from the ene-diols (6/7) and uses a sequence of Claisen rearrangement, 1,2-O-O-silyl migration and S(N)2'-cyclization reactions (9b --> 10a/b via 11a/b).