(3R,6R)-2,6-dimethyl-7-octene-2,3,6-triol

• 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: (3R,6R)-2,6-dimethyl-7-octene-2,3,6-triol
• 英文别名: (3R,6R)-2,6-dimethyloct-7-ene-2,3,6-triol；(3r,6r)-2,6-Dimethyloct-7-ene-2,3,6-triol
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: CNYFGLAROLNGDG-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,6R)-2,6-dimethyl-7-octene-2,3,6-triol 在 1% Pd/C 氢气 作用下， 生成
  参考文献：
  名称：

  Selective Aliphatic C-H Oxidation

  摘要：

  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。

  公开号：

  US20110015397A1
• 作为产物：
  描述：

  (R)-芳樟醇 在 AD-mix-α 、 四氧化锇 作用下， 生成 (3R,6S)-6,7-dihydroxy-6,7-dihydrolinalool 、 (3R,6R)-2,6-dimethyl-7-octene-2,3,6-triol
  参考文献：
  名称：

  Asymmetric dihydroxylation of linalool, nerolidol and citronellyl acetate. Enantioselective synthesis of (3S, 6S)-tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran-3-ol

  摘要：

  The asymmetric Sharpless' dihydroxylation of linalool, citronellyl acetate and nerolidol was investigated. High diastereo-. enantio- and positional selectivity was observed for the first two terpenes. A highly diastereo- and enantioselective synthesis of (3S,6S)-tetrahydro- 2,2,6-trimethyl - 6-vinyl-2H -pyran-3-ol is described.

  DOI：

  10.1016/s0040-4039(00)91832-x

文献信息

• Heteroatom-Directed Acylation of Secondary Alcohols To Assign Absolute Configuration
  作者：Alexander S. Burns、Christopher C. Ross、Scott D. Rychnovsky

  DOI：10.1021/acs.joc.7b03156

  日期：2018.3.2

  is effective for the enantioselective acylation and kinetic resolution of benzylic secondary alcohols. The enantioselective acylation has now been extended to secondary alcohols bearing electron-withdrawing groups such as halides and other heteroatoms. The level of selectivity is modest to good and is sufficient for determining configuration using the competing enantioselective conversion method. A

  Birman的HBTM催化剂对苄基仲醇的对映选择性酰化和动力学拆分有效。对映选择性酰化现已扩展到带有吸电子基团的仲醇，例如卤化物和其他杂原子。选择性水平适中，足以使用竞争对映选择性转化方法确定构型。数学分析确定了实现最大转换差异的条件，因此，可以更有把握地分配配置。该新方法对卤代醇和仲1，2-叔二醇有效，并用于确认两种inoterpene天然产物的构型。
• The directed dihydroxylation of allylic alcohols
  作者：Timothy J. Donohoe、Peter R. Moore、Michael J. Waring、Nicholas J. Newcombe

  DOI：10.1016/s0040-4039(97)01061-7

  日期：1997.7

  The preparation and dihydroxylation of a series of polyenes and cyclic allylic alcohols using the TMEDA/osmium tetroxide mixture is reported. Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydrogen-bonds to the allylic alcohol group. A mechanistic hypothesis is presented which invokes the formation of a reactive, bidentate complex between osmium

  报道了使用TMEDA /四氧化os混合物制备一系列多烯和环状烯丙基醇并进行二羟基化。值得注意的是，由于氧化剂氢键合到烯丙基醇基团上，因此这些试剂导致高水平的区域化学和立体化学控制。提出了一种机械假说，该假说在低温下引起四氧化和TMEDA之间的反应性双齿络合物的形成。
• US7829342B2
  申请人：——

  公开号：US7829342B2

  公开（公告）日：2010-11-09
• 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。
• Asymmetric dihydroxylation of linalool, nerolidol and citronellyl acetate. Enantioselective synthesis of (3S, 6S)-tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran-3-ol
  作者：Giovanni Vidari、Andrea Giori、Antonella Dapiaggi、Gianluigi Lanfranchi

  DOI：10.1016/s0040-4039(00)91832-x

  日期：1993.10

  The asymmetric Sharpless' dihydroxylation of linalool, citronellyl acetate and nerolidol was investigated. High diastereo-. enantio- and positional selectivity was observed for the first two terpenes. A highly diastereo- and enantioselective synthesis of (3S,6S)-tetrahydro- 2,2,6-trimethyl - 6-vinyl-2H -pyran-3-ol is described.