((((5S,6R,7S,8S,9S,Z)-tetradec-10-ene-1,5,6,7,8,9-hexayl)hexakis(oxy))hexakis(methylene))hexabenzene | 636587-25-2

• 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: ((((5S,6R,7S,8S,9S,Z)-tetradec-10-ene-1,5,6,7,8,9-hexayl)hexakis(oxy))hexakis(methylene))hexabenzene
• CAS: 636587-25-2
• 化学式: C₅₆H₆₄O₆
• 分子量: 833.121
• InChiKey: DDEJBCUVAKPLGL-WODSOPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.66
• 重原子数：
  62.0
• 可旋转键数：
  29.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((((5S,6R,7S,8S,9S,Z)-tetradec-10-ene-1,5,6,7,8,9-hexayl)hexakis(oxy))hexakis(methylene))hexabenzene 在 N-甲基吗啉 、 四氧化锇 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 24.0h， 以53%的产率得到(4S,5S,6S,7S,8S,9R,10S)-6,7,8,9,10,14-Hexakis-benzyloxy-tetradecane-4,5-diol
  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：

  (Z)-(6R,7R,8S)-1,6,7,8-Tetrakis-benzyloxy-undec-9-en-5-ol 在 喹啉 、 Lindlar's catalyst 、 乙基溴化镁 、 氢气 、 sodium acetate 、 四丁基碘化铵 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.25h， 生成 ((((5S,6R,7S,8S,9S,Z)-tetradec-10-ene-1,5,6,7,8,9-hexayl)hexakis(oxy))hexakis(methylene))hexabenzene
  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