(E)-(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide | 162582-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide
• 英文别名: (E,3R,6S)-6-[tert-butyl(diphenyl)silyl]oxy-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-dimethylhept-4-enamide
• CAS: 162582-68-5
• 化学式: C₃₀H₄₃NO₄Si
• 分子量: 509.761
• InChiKey: UNFGIRYKWMJNRB-OXXAPRFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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)-(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 、 potassium carbonate 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 50.0h， 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：

  [(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-oxo-butyl]-phosphonic acid dimethyl ester 在 L-Selectride 、 lithium diisopropyl amide 作用下， 反应 24.0h， 生成 (E)-(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-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).