[(3S,4R)-4-(2,2-dimethylpropanoyloxy)-5-oxopent-1-en-3-yl] 2,2-dimethylpropanoate | 1393535-32-4

• 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: [(3S,4R)-4-(2,2-dimethylpropanoyloxy)-5-oxopent-1-en-3-yl] 2,2-dimethylpropanoate
• CAS: 1393535-32-4
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: SLJGOZPRWDEPEE-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  磷酰基乙酸三乙酯 、 [(3S,4R)-4-(2,2-dimethylpropanoyloxy)-5-oxopent-1-en-3-yl] 2,2-dimethylpropanoate 在 lithium chloride 作用下， 反应 5.0h， 生成 、 ethyl (2E,4S,5S)-4,5-bis(2,2-dimethylpropanoyloxy)hepta-2,6-dienoate
  参考文献：
  名称：

  Convenient strategy for the synthesis of highly functionalizable hydroxylated unsaturated azepanes

  摘要：

  A convenient approach to the construction of dihydroxylated unsaturated azepanes featuring a functional group (ethoxycarbonyl)methyl or (cyano)methyl at C-2 was achieved from a pent-4-enal synthon obtained in four steps from D-xylose. The key step of the sequence relied on the conjugate addition of allylamine to alpha,beta-unsaturated ester or nitrile, prepared by Wadsworth-Emmons olefination. Subsequent RCM afforded the target unsaturated azepanes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.053
• 作为产物：
  描述：

  D-木糖 在 吡啶 、 盐酸 、 水 、 对甲苯磺酰氯 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 108.0h， 生成 [(3S,4R)-4-(2,2-dimethylpropanoyloxy)-5-oxopent-1-en-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Convenient strategy for the synthesis of highly functionalizable hydroxylated unsaturated azepanes

  摘要：

  A convenient approach to the construction of dihydroxylated unsaturated azepanes featuring a functional group (ethoxycarbonyl)methyl or (cyano)methyl at C-2 was achieved from a pent-4-enal synthon obtained in four steps from D-xylose. The key step of the sequence relied on the conjugate addition of allylamine to alpha,beta-unsaturated ester or nitrile, prepared by Wadsworth-Emmons olefination. Subsequent RCM afforded the target unsaturated azepanes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.053

文献信息

• Convenient strategy for the synthesis of highly functionalizable hydroxylated unsaturated azepanes
  作者：Sophie Goumain、Hanaa Taghzouti、Charles Portella、Jean-Bernard Behr、Richard Plantier-Royon

  DOI：10.1016/j.tetlet.2012.06.053

  日期：2012.8

  A convenient approach to the construction of dihydroxylated unsaturated azepanes featuring a functional group (ethoxycarbonyl)methyl or (cyano)methyl at C-2 was achieved from a pent-4-enal synthon obtained in four steps from D-xylose. The key step of the sequence relied on the conjugate addition of allylamine to alpha,beta-unsaturated ester or nitrile, prepared by Wadsworth-Emmons olefination. Subsequent RCM afforded the target unsaturated azepanes. (C) 2012 Elsevier Ltd. All rights reserved.