(E)-8-(benzyloxy)oct-2-ene-1,7-diol | 1010081-61-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-8-(benzyloxy)oct-2-ene-1,7-diol
• 英文别名: (E)-8-phenylmethoxyoct-2-ene-1,7-diol
• CAS: 1010081-61-4
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: RSZPHFHKCHCUKH-FARCUNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (E)-8-(benzyloxy)oct-2-ene-1,7-diol 在 三苯基膦氯金 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到cis-2-(benzyloxymethyl)-6-vinyl-tetrahydro-2H-pyran
  参考文献：
  名称：

  Au-Catalyzed Cyclization of Monoallylic Diols

  摘要：

  The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78 degrees C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.

  DOI：

  10.1021/ol703002p
• 作为产物：
  描述：

  (E)-1-(benzyloxy)-8-(tert-butyldimethylsilyloxy)oct-6-en-2-ol 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以82%的产率得到(E)-8-(benzyloxy)oct-2-ene-1,7-diol
  参考文献：
  名称：

  Au-Catalyzed Cyclization of Monoallylic Diols

  摘要：

  The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78 degrees C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.

  DOI：

  10.1021/ol703002p

文献信息

• Au-Catalyzed Cyclization of Monoallylic Diols
  作者：Aaron Aponick、Chuan-Ying Li、Berenger Biannic

  DOI：10.1021/ol703002p

  日期：2008.2.1

  The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78 degrees C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.