(E)-(R)-1-Benzyloxy-dec-6-en-5-ol | 636586-42-0

• 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)-(R)-1-Benzyloxy-dec-6-en-5-ol
• CAS: 636586-42-0
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: XWKFYWNDRXCHEK-QJXUFPCYSA-N

反应信息

• 作为反应物：
  描述：

  (E)-(R)-1-Benzyloxy-dec-6-en-5-ol 在 N-甲基吗啉 、 四氧化锇 、 四丁基碘化铵 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 45.0h， 生成 (5R,6R,7S)-Decane-1,5,6,7-tetraol
  参考文献：
  名称：

  Universal NMR Databases for Contiguous Polyols

  摘要：

  On the basis of 1,2,3-triols 1asimilar tod, 1,2,3,4-tetraols 2asimilar toh, and 1,2,3,4,5-pentaols 3asimilar top, NMR databases with four types of profile-descriptors (C-13-, H-1-, and H-1(OH)-chemical shifts and vicinal spin-coupling constants) for contiguous polyols are reported. To systematically assess the relative values of these databases, a case study has been conducted on heptaols 4asimilar tod, through which the gamma- and delta-effects have been recognized to refine the C-13 and H-1 chemical shift profile predicted via an application of the concept of self-contained nature. The magnitudes of gamma- and delta-effects depend on a specific stereochemical arrangement of the functional groups present in both the inside and outside of a self-contained box and are significant only for the stereoisomers belonging to a specific sub-group. With the exception of the stereochemical arrangement of functional groups belonging to a specific sub-group, the gamma- and delta-effects can, at the first order of approximation, be ignored for the stereochemical analysis of unknown compounds. For the stereoisomers belonging to a specific sub-group, it is necessary to refine, with incorporation of the gamma- and delta-effects, the profile predicted at the first order of approximation. With use of heptaols 4asimilar tod, the values of (3)J(H,H) profiles have been assessed. Two methods, one using profiles consisting of three contiguous (3)J(H,H) constants and the other using profiles consisting of two contiguous (3)J(H,H) constants, have been developed. A stereochemical analysis based on three, or two, contiguous (3)J(H,H) profiles is operationally simpler than one based on C-13 and H-1 chemical shift profiles. Therefore, it is recommended to use a (3)J(H,H) profile as the primary device to predict the stereochemistry of unknown polyols and C-13 and H-1 chemical shift profiles as the secondary devices to confirm the predicted stereochemistry.

  DOI：

  10.1021/ja0375481
• 作为产物：
  描述：

  (R)-1-Benzyloxy-dec-6-yn-5-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以81%的产率得到(E)-(R)-1-Benzyloxy-dec-6-en-5-ol
  参考文献：
  名称：

  Universal NMR Databases for Contiguous Polyols

  摘要：

  On the basis of 1,2,3-triols 1asimilar tod, 1,2,3,4-tetraols 2asimilar toh, and 1,2,3,4,5-pentaols 3asimilar top, NMR databases with four types of profile-descriptors (C-13-, H-1-, and H-1(OH)-chemical shifts and vicinal spin-coupling constants) for contiguous polyols are reported. To systematically assess the relative values of these databases, a case study has been conducted on heptaols 4asimilar tod, through which the gamma- and delta-effects have been recognized to refine the C-13 and H-1 chemical shift profile predicted via an application of the concept of self-contained nature. The magnitudes of gamma- and delta-effects depend on a specific stereochemical arrangement of the functional groups present in both the inside and outside of a self-contained box and are significant only for the stereoisomers belonging to a specific sub-group. With the exception of the stereochemical arrangement of functional groups belonging to a specific sub-group, the gamma- and delta-effects can, at the first order of approximation, be ignored for the stereochemical analysis of unknown compounds. For the stereoisomers belonging to a specific sub-group, it is necessary to refine, with incorporation of the gamma- and delta-effects, the profile predicted at the first order of approximation. With use of heptaols 4asimilar tod, the values of (3)J(H,H) profiles have been assessed. Two methods, one using profiles consisting of three contiguous (3)J(H,H) constants and the other using profiles consisting of two contiguous (3)J(H,H) constants, have been developed. A stereochemical analysis based on three, or two, contiguous (3)J(H,H) profiles is operationally simpler than one based on C-13 and H-1 chemical shift profiles. Therefore, it is recommended to use a (3)J(H,H) profile as the primary device to predict the stereochemistry of unknown polyols and C-13 and H-1 chemical shift profiles as the secondary devices to confirm the predicted stereochemistry.

  DOI：

  10.1021/ja0375481