(4R,5S,6R)-5,6-diallyloxy-7-oxy-heptano-1,4-lactone | 1147996-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5S,6R)-5,6-diallyloxy-7-oxy-heptano-1,4-lactone
• 英文别名: (2S,3S)-3-[(2R)-5-oxooxolan-2-yl]-2,3-bis(prop-2-enoxy)propanal
• CAS: 1147996-12-0
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: QTOCRUQZFNNIKU-WZRBSPASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-5,6-diallyloxy-7-oxy-heptano-1,4-lactone 、 叔丁基二甲硅基三氟甲磺酸酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以81%的产率得到(1S,2S,3S,4S,5R)-2-(tert-butyldimethylsilyloxy)-3,4-diallyloxy-6-oxa-bicyclo[3,2,1]octan-7-one
  参考文献：
  名称：

  Asymmetric syntheses of (−)-methyl shikimate and (−)-5a-carba-β-d-gulopyranose from d-arabinose via Mukaiyama-type intramolecular aldolization

  摘要：

  New asymmetric syntheses of (-)-methyl shikimate 1 and (-)-5a-carba-beta-D-gulopyranose 11 from D-arabinose through a common route which employed Mukaiyama-type intramolecular aldolization as a key step were described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.028
• 作为产物：
  描述：

  (4R,5S,6R)-5,6-diallyloxy-7-hydroxy-heptano-1,4-lactone 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到(4R,5S,6R)-5,6-diallyloxy-7-oxy-heptano-1,4-lactone
  参考文献：
  名称：

  Asymmetric syntheses of (−)-methyl shikimate and (−)-5a-carba-β-d-gulopyranose from d-arabinose via Mukaiyama-type intramolecular aldolization

  摘要：

  New asymmetric syntheses of (-)-methyl shikimate 1 and (-)-5a-carba-beta-D-gulopyranose 11 from D-arabinose through a common route which employed Mukaiyama-type intramolecular aldolization as a key step were described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.028

文献信息

• Asymmetric syntheses of (−)-methyl shikimate and (−)-5a-carba-β-d-gulopyranose from d-arabinose via Mukaiyama-type intramolecular aldolization
  作者：Shi-Ling Liu、Xiao-Xin Shi、Yu-Lan Xu、Wei Xu、Jing Dong

  DOI：10.1016/j.tetasy.2008.12.028

  日期：2009.1

  New asymmetric syntheses of (-)-methyl shikimate 1 and (-)-5a-carba-beta-D-gulopyranose 11 from D-arabinose through a common route which employed Mukaiyama-type intramolecular aldolization as a key step were described. (C) 2009 Elsevier Ltd. All rights reserved.