(S)-8-bromo-2,6-dimethyloctan-2-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-8-bromo-2,6-dimethyloctan-2-ol
• 英文别名: (6S)-8-bromo-2,6-dimethyloctan-2-ol
• 化学式: C₁₀H₂₁BrO
• 分子量: 237.18
• InChiKey: NOFRKCKHVRRXNL-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-8-bromo-2,6-dimethyloctan-2-ol 在 perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 作用下， 以 一氟三氯甲烷 为溶剂， 反应 21.0h， 生成 (6R)-8-bromo-2,6-dimethyloctane-2,6-diol
  参考文献：
  名称：

  Highly Enantiospecific Oxyfunctionalization of Nonactivated Hydrocarbon Sites by Perfluoro-cis-2-n-butyl-3-n-propyloxaziridine

  摘要：

  [GRAPHICS]Nonactivated hydrocarbon sites of enantiopure compounds are oxyfunctionalized enantiospecifically by perfluoro-cis-2-n-butyl-3-n-propyloxaziridine under remarkably mild reaction conditions. The reaction occurs with retention of configuration at the oxidized stereogenic center, and the enantiospecificity is highly independent from both the carbon framework of the substrate and the presence of functional groups.

  DOI：

  10.1021/ol990594e
• 作为产物：
  描述：

  (S)-(+)-溴化香茅酯 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-8-bromo-2,6-dimethyloctan-2-ol
  参考文献：
  名称：

  Highly Enantiospecific Oxyfunctionalization of Nonactivated Hydrocarbon Sites by Perfluoro-cis-2-n-butyl-3-n-propyloxaziridine

  摘要：

  [GRAPHICS]Nonactivated hydrocarbon sites of enantiopure compounds are oxyfunctionalized enantiospecifically by perfluoro-cis-2-n-butyl-3-n-propyloxaziridine under remarkably mild reaction conditions. The reaction occurs with retention of configuration at the oxidized stereogenic center, and the enantiospecificity is highly independent from both the carbon framework of the substrate and the presence of functional groups.

  DOI：

  10.1021/ol990594e

文献信息

• Selective Aliphatic C-H Oxidation
  申请人：White M. Christina

  公开号：US20110015397A1

  公开（公告）日：2011-01-20

  A composition including a complex of a metal, a tetradentate ligand, at least one ancillary ligand, and a counterion may be used for selective sp 3 C—H bond oxidation. The tetradentate ligand may include a N-heterocyclic-N,N′-bis(pyridyl)-ethane-1,2-diamine group or a N,N′-bis(heterocyclic)-N,N′-bis(pyridyl)-ethane-1,2-diamine group. The composition can be used in combination with H 2 O 2 to effect highly selective oxidations of unactivated sp 3 C—H bonds over a broad range of substrates. The site of oxidation can be predicted, based on the electronic and/or steric environment of the C—H bond. In addition, the oxidation reaction does not require the presence of directing groups in the substrate.

  一种包括金属复合物、四齿配体、至少一种辅助配体和对离子的组合物可用于选择性氧化sp3C—H键。四齿配体可能包括N-杂环-N,N′-双(吡啶基)-乙烷-1,2-二胺基团或N,N′-双(杂环)-N,N′-双(吡啶基)-乙烷-1,2-二胺基团。该组合物可与H2O2结合使用，对广泛范围的底物进行高度选择性的氧化未活化的sp3C—H键。可以根据C—H键的电子和/或立体环境预测氧化位置。此外，氧化反应不需要底物中存在导向基团。
• The Fe(PDP)-catalyzed aliphatic C–H oxidation: a slow addition protocol
  作者：Nicolaas A. Vermeulen、Mark S. Chen、M. Christina White

  DOI：10.1016/j.tet.2008.11.082

  日期：2009.4

  This report describes a slow addition protocol for the Fe(PDP)-catalyzecl aliphatic C-H oxidation reaction. Under this protocol, the reaction can be productively driven to higher conversions without decreasing site-selectivity or chemoselectivity. The operational advantages of this procedure are highlighted in the oxidation of two complex natural product derivatives. Hydroxylated products can be obtained in high isolated yields without the need for recycling recovered starting materials. (C) 2008 Published by Elsevier Ltd.
• US7829342B2
  申请人：——

  公开号：US7829342B2

  公开（公告）日：2010-11-09
• Highly Enantiospecific Oxyfunctionalization of Nonactivated Hydrocarbon Sites by Perfluoro-<i>cis</i>-2-<i>n</i>-butyl-3-<i>n</i>-propyloxaziridine
  作者：Alberto Arnone、Stefania Foletto、Pierangelo Metrangolo、Massimo Pregnolato、Giuseppe Resnati

  DOI：10.1021/ol990594e

  日期：1999.7.1

  [GRAPHICS]Nonactivated hydrocarbon sites of enantiopure compounds are oxyfunctionalized enantiospecifically by perfluoro-cis-2-n-butyl-3-n-propyloxaziridine under remarkably mild reaction conditions. The reaction occurs with retention of configuration at the oxidized stereogenic center, and the enantiospecificity is highly independent from both the carbon framework of the substrate and the presence of functional groups.