(+/-)-2-methylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate | 1185060-33-6

• 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: (+/-)-2-methylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate
• 英文别名: 2-methylhex-5-en-3-yl N-(4-nitrophenyl)sulfonylcarbamate
• CAS: 1185060-33-6
• 化学式: C₁₄H₁₈N₂O₆S
• 分子量: 342.373
• InChiKey: KNTJVSZJTRPTSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-2-methylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate 在 (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 1,2-二苯亚磺酰基乙烷 、 氧气 、 苯基-P-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (+/-)-(4S,5R)-5-isopropyl-3-(4-nitrophenylsulfonyl)-4-vinyloxazolidin-2-one 、 (+/-)-(4R,5R)-5-isopropyl-3-(4-nitrophenylsulfonyl)-4-vinyloxazolidin-2-one
  参考文献：
  名称：

  Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst

  摘要：

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.064
• 作为产物：
  描述：

  2-甲基-5-己烯-3-醇 、 4-nitrobenzenesulfonyl isocyanate 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (+/-)-2-methylhex-5-en-3-yl 4-nitrophenylsulfonylcarbamate
  参考文献：
  名称：

  Allylic C−H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs

  摘要：

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

  DOI：

  10.1021/ja9054959

文献信息

• Diversification of a β-lactam pharmacophore via allylic C–H amination: accelerating effect of Lewis acid co-catalyst
  作者：Xiangbing (Ben) Qi、Grant T. Rice、Manjinder S. Lall、Mark S. Plummer、M. Christina White

  DOI：10.1016/j.tet.2010.04.064

  日期：2010.6

  This report describes the use of Pd(II)/bis-sulfoxide 1 catalyzed intra- and intermolecular allylic C-H amination reactions to rapidly diversify structures containing a sensitive beta-lactam core similar to that found in the monobactam antibiotic Aztreonam. Pharmacologically interesting oxazolidinone, oxazinanone, and linear amine motifs are rapidly installed with predictable and high selectivities under conditions that use limiting amounts of substrate. Additionally, we demonstrate for the first time that intramolecular C-H amination processes may be accelerated using catalytic amounts of a Lewis acid co-catalyst [Cr(III)(salen)Cl 2]. (C) 2010 Elsevier Ltd. All rights reserved.
• Allylic C−H Amination for the Preparation of <i>syn</i>-1,3-Amino Alcohol Motifs
  作者：Grant T. Rice、M. Christina White

  DOI：10.1021/ja9054959

  日期：2009.8.26

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.