2-(5-cyclohexylpenta-2'E,4'E-dienoylamino)-1,4-benzoquinone | 208706-21-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-cyclohexylpenta-2'E,4'E-dienoylamino)-1,4-benzoquinone
• 英文别名: 2-(5-Cyclohexylpentadienamido)-1,4-benzoquinone；(2E,4E)-5-cyclohexyl-N-(3,6-dioxocyclohexa-1,4-dien-1-yl)penta-2,4-dienamide
• CAS: 208706-21-2
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: SHVHEYVINKOTTB-KBXRYBNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-cyclohexylpenta-2'E,4'E-dienoylamino)-1,4-benzoquinone 在 叔丁基过氧化氢 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 为溶剂， 反应 0.01h， 生成 (+/-)-nisamycin
  参考文献：
  名称：

  The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

  摘要：

  DOI：

  10.1055/s-1998-2064
• 作为产物：
  描述：

  (2E,4E)-5-cyclohexyl-N-(6,6-dimethoxy-3-oxocyclohexa-1,4-dien-1-yl)penta-2,4-dienamide 在 amberlyst-15 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-(5-cyclohexylpenta-2'E,4'E-dienoylamino)-1,4-benzoquinone
  参考文献：
  名称：

  The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

  摘要：

  DOI：

  10.1055/s-1998-2064

文献信息

• Epoxidation of Electron Deficient Alkenes Using <i>tert</i>-Butyl Hydroperoxide and 1,5,7-Triazabicyclo[4.4.0]dec-5-ene and its Derivatives
  作者：Thorsten Genski、Gregor Macdonald、Xudong Wei、Norman Lewis、Richard J. K. Taylor

  DOI：10.1055/s-1999-2721

  日期：1999.6

  The title cyclic guanidine (4a) is an efficient promoter of enone epoxidation by tert-butyl hydroperoxide. Optimisation studies are reported and the procedure applied to cyclic and acyclic ketones, quinones and naphthoquinones. N-Substituted guanidine (4c) proved best for the epoxidation of 2-amidobenzoquinones. Preliminary asymmetric epoxidation studies are also discussed.

  标题中的环状胍（4a）是一种高效促进叔丁基过氧化氢对烯酮环氧化反应的催化剂。报道了优化研究，并将该方法应用于环状和非环状酮、醌和萘醌的环氧化反应。N-取代胍（4c）证明是2-酰胺苯醌环氧化反应的最佳催化剂。初步不对称环氧化研究也进行了讨论。
• Dwyer, Catherine L.; Gill, Christopher D.; Ichihara, Osamu, Synlett, 2000, # 5, p. 704 - 706
  作者：Dwyer, Catherine L.、Gill, Christopher D.、Ichihara, Osamu、Taylor, Richard J. K.

  DOI：——

  日期：——
• The design and synthesis of novel anomeric hydroperoxides: influence of the carbohydrate residue in the enantioselective epoxidation of quinones
  作者：Abass Bundu、Neil G. Berry、Christopher D. Gill、Catherine L. Dwyer、Andrew V. Stachulski、Richard J.K. Taylor、John Whittall

  DOI：10.1016/j.tetasy.2004.11.015

  日期：2005.1

  We present a study of the base (DBU)-catalysed epoxidation of a number of important naturally occurring quinones using a series of pyranose-derived anomeric hydroperoxides. The absolute (viz. D or L) stereochemistry of the carbohydrate, electronic nature of the 6-substituent and ring substitution are all important variables. both for the formation of the hydroperoxide and its reactivity. Reactions studied were the epoxidation of a precursor of the natural antibiotic. alisamycin and a series of naphthoquinones related to Vitamin K. In the best case, an ee of 82% was obtained; either product enantiomer is accesssible according to the absolute stereochemistry of the carbohydrate. Finally, a molecular modelling study of the reaction is reported, concluding chat the reactions are under kinetic control and that the observed ees cannot be explained by considering transition states, that involve only the quinone and peroxide anion. It seems likely that the DBU molecule may., play a key role in the transition state. (C) 2004 Elsevier Ltd. All rights reserved.