(2R,3S)-2,3-dihydroxy-1-cyclohexylcyclohexa-4,6-diene | 291749-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-2,3-dihydroxy-1-cyclohexylcyclohexa-4,6-diene
• 英文别名: (1S,2R)-3-(1-cyclohexyl)-3,5-cyclohexadien-1,2-diol；(1s,2r)-3-(1-Cyclohexyl)-3,5-cyclohexadiene-1,2-diol；(1S,2R)-3-cyclohexylcyclohexa-3,5-diene-1,2-diol
• CAS: 291749-84-3
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: VBTUINDTJFZZLS-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2,3-dihydroxy-1-cyclohexylcyclohexa-4,6-diene 在 potassium diazodicarboxylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxol-4-yl)cyclohexane
  参考文献：
  名称：

  Toluene dioxygenase-mediated oxidation of aromatic substrates with remote chiral centers

  摘要：

  几种含有远程手性中心的芳香底物被施加于表达在阻断突变体和重组生物体中的甲苯和萘双加氧酶，产生了 cis-二醇代谢产物，几乎没有动力学分离。

  DOI：

  10.1039/b002143l

文献信息

• Enantiopurity and absolute configuration determination of arene<i>cis</i>-dihydrodiol metabolites and derivatives using chiral boronic acids
  作者：Derek R. Boyd、Narain D. Sharma、Peter A. Goodrich、John F. Malone、Gareth McConville、John S. Harrison、Paul J. Stevenson、Christopher C.R. Allen

  DOI：10.1002/chir.22764

  日期：2018.1

  cis‐dihydrodiol, cyclohex‐2‐en‐1‐one cis‐diol, heteroarene cis/trans‐2,3‐diol, and catechol metabolites in estimating their ee values, and 2) new chiral phenylboronic acids, 2‐[1‐methoxy‐2,2‐dimethylpropyl]phenyl boronic acid (MDPBA) and 2‐[1‐methoxy‐1‐phenylmethyl]phenyl boronic acid (MPPBA) and their advantages over MEPBA, as reagents for stereochemical analysis of arene and alkene cis‐diol metabolites, are presented

  的用于确定对映体过量（方法相对优点EE）值和手性芳烃绝对构型和烯烃的顺式-1,2-二醇的代谢物，包括硼酸酯的形成，使用外消旋或对映纯的（+）和（ - ） - 2-讨论了（1-甲氧基乙基）苯基硼酸（MEPBA）。的进一步的应用：1）衍生MEPBA手性的单-和多环芳烃的硼酸盐顺式-dihydrodiol，环己-2-烯-1-酮的顺式-二醇，杂芳烃顺/反式-2,3-二醇，和儿茶酚代谢物在估计他们的ee值； 2）新的手性苯基硼酸，2- [1- [1-甲氧基-2,2-二甲基丙基]苯基硼酸（MDPBA）和2- [1-甲氧基-1-苯基甲基]苯基硼酸（MPPBA）及其优势介绍了在MEPBA上作为芳烃和烯烃顺式-二醇代谢物的立体化学分析试剂。
• A study of substrate specificity of toluene dioxygenase in processing aromatic compounds containing benzylic and/or remote chiral centers
  作者：Vu P. Bui、Trond Vidar Hansen、Yngve Stenstrøm、Tomas Hudlicky、Douglas W. Ribbons

  DOI：10.1039/b006545p

  日期：——

  A series of substituted arenes containing remote chiral centers were screened as substrates for toluene dioxygenase (TDO). The absolute stereochemistry of the new metabolites was determined by chemical and spectroscopic correlation with synthetic standards. There was no evidence for kinetic resolution; enantiomers were indiscriminately processed by the enzyme to diastereomeric pairs, which were separable

  一系列替代 竞技场 筛选了包含远程手性中心的底物 甲苯 双加氧酶（TDO）。新产品的绝对立体化学代谢物通过化学和光谱相关性与合成标准品测定。没有动力学分解的证据。该酶将对映异构体不加区别地加工成非对映异构体对，这些非对映异构体可在衍生化后分离。其中一些新代谢物 可用作合成子 吗啡合成。对于那些对分离稳定的新化合物及其不稳定化合物的衍生物，已报道了完整的实验细节。
• Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines
  作者：Lukas Werner、Jason Reed Hudlicky、Martina Wernerova、Tomas Hudlicky

  DOI：10.1016/j.tet.2010.03.059

  日期：2010.5

  Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds. (C) 2010 Elsevier Ltd. All rights reserved.