(D-arabino)-4-benzyloxyhepta-1,6-diene-3,5-diol | 1013644-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (D-arabino)-4-benzyloxyhepta-1,6-diene-3,5-diol
• 英文别名: (3R,5R)-4-phenylmethoxyhepta-1,6-diene-3,5-diol
• CAS: 1013644-36-4
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: URTSGBKBEQEJER-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (D-arabino)-4-benzyloxyhepta-1,6-diene-3,5-diol 、 一氧化碳 在 palladium dichloride sodium acetate 、 溶剂黄146 、 copper dichloride 作用下， 反应 0.5h， 以78%的产率得到(1R,5S,7R,8R)-8-benzyloxy-7-vinyl-2,6-dioxabicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Stereocontrolled oxycarbonylation of 4-benzyloxyhepta-1,6-diene-3,5-diols promoted by chiral palladium(II) complexes

  摘要：

  The synthesis of all diastereomers of 4-benzyloxyhepta-1,6-diene-3,5-diols 8-10 is described. The diastereo- and enantioselectivity of palladium(II)-catalysed oxycarbonylation of the symmetric compounds 8-10 were studied. The substrates 8-10 underwent Pd(II)-initiated oxycarbonylative bicyclisation to afford bicyclic lactones 11-14 in good yields and with excellent threo-diastereoselectivity. Additionally, the synthesis of enantiomerically pure lactone D-gluco-12, precursor for syntheses of goniofufurone and 7-epi-gonio-fufurone, was developed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.12.003
• 作为产物：
  描述：

  三甲基碘化锍 、 (2R,4R)-1,2:4,5-dianhydro-3-(benzyl)arabitol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以60%的产率得到(D-arabino)-4-benzyloxyhepta-1,6-diene-3,5-diol
  参考文献：
  名称：

  Stereocontrolled oxycarbonylation of 4-benzyloxyhepta-1,6-diene-3,5-diols promoted by chiral palladium(II) complexes

  摘要：

  The synthesis of all diastereomers of 4-benzyloxyhepta-1,6-diene-3,5-diols 8-10 is described. The diastereo- and enantioselectivity of palladium(II)-catalysed oxycarbonylation of the symmetric compounds 8-10 were studied. The substrates 8-10 underwent Pd(II)-initiated oxycarbonylative bicyclisation to afford bicyclic lactones 11-14 in good yields and with excellent threo-diastereoselectivity. Additionally, the synthesis of enantiomerically pure lactone D-gluco-12, precursor for syntheses of goniofufurone and 7-epi-gonio-fufurone, was developed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.12.003

文献信息

• Stereocontrolled oxycarbonylation of 4-benzyloxyhepta-1,6-diene-3,5-diols promoted by chiral palladium(II) complexes
  作者：Peter Kapitán、Tibor Gracza

  DOI：10.1016/j.tetasy.2007.12.003

  日期：2008.1

  The synthesis of all diastereomers of 4-benzyloxyhepta-1,6-diene-3,5-diols 8-10 is described. The diastereo- and enantioselectivity of palladium(II)-catalysed oxycarbonylation of the symmetric compounds 8-10 were studied. The substrates 8-10 underwent Pd(II)-initiated oxycarbonylative bicyclisation to afford bicyclic lactones 11-14 in good yields and with excellent threo-diastereoselectivity. Additionally, the synthesis of enantiomerically pure lactone D-gluco-12, precursor for syntheses of goniofufurone and 7-epi-gonio-fufurone, was developed. (c) 2007 Elsevier Ltd. All rights reserved.