tert-butyl cyano(4-nitrophenyl)acetate | 724767-53-7

• 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: tert-butyl cyano(4-nitrophenyl)acetate
• 英文别名: Tert-butyl 2-cyano-2-(4-nitrophenyl)acetate
• CAS: 724767-53-7
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: JFYXRWBEVKYMLS-UHFFFAOYSA-N

物化性质

• 沸点：
  399.5±32.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl cyano(4-nitrophenyl)acetate 以 hexafluoropropan-2-ol 为溶剂， 反应 1.0h， 以96%的产率得到对硝基苯乙腈
  参考文献：
  名称：

  A novel practical cleavage of tert-butyl esters and carbonates using fluorinated alcohols

  摘要：

  Thermolytic cleavage of t-butyl esters and t-butyl carbonates was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvent. Thus, a practical method to cleanly convert t-butyl esters and carbonates into the corresponding carboxylic acids, decarboxylated products, or alcohols in nearly quantitative yields was developed. The product is recovered by a simple solvent evaporation. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic esters. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.100
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 对硝基苯乙腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以90%的产率得到tert-butyl cyano(4-nitrophenyl)acetate
  参考文献：
  名称：

  二碳酸二叔丁酯：一种多功能的羧化试剂

  摘要：

  通过非亲核碱（LDA）生成的碳亲核试剂被有效捕集与二-叔丁基二碳酸酯（Boc-酸酐），以提供相应的叔丁基的芳基乙酸酯，二-叔丁基的芳基丙二酸酯，芳不对称丙二和叔高产率的苯甲酸丁酯。该反应表示准备各种的另一种有用的方式叔丁基羧酸盐和二-亮点的合成效用叔丁基二碳酸酯作为多功能羧试剂。

  DOI：

  10.1016/j.tet.2008.10.089

文献信息

• DEPROTECTION OF BOC-PROTECTED COMPOUNDS
  申请人：Choy Jason Chi-Chung

  公开号：US20100311968A1

  公开（公告）日：2010-12-09

  Organic compounds having t-butyl ester or BOC carbonate protecting groups are effectively deprotected by heating in a fluorinated alcohol solution.

  具有叔丁基酯或BOC碳酸酯保护基团的有机化合物可通过在氟代醇溶液中加热有效地去保护。
• Asymmetric Construction of Quaternary Stereocenters by Direct Organocatalytic Amination of α-Substituted α-Cyanoacetates and β-Dicarbonyl Compounds
  作者：Steen Saaby、Marco Bella、Karl Anker Jørgensen

  DOI：10.1021/ja047704j

  日期：2004.7.1

  The first organocatalytic highly enantioselective reactions of substituted alpha-cyanoacetates and beta-dicarbonyl compounds with azodicarboxylates are reported. In the presence of 0.1-5 mol % of a quinidine-derived alkaloid beta-ICD, optically active quaternary hydrazine adducts are obtained in very high yields and with enantioselectivities up to >98% ee. A two-step procedure for the cleavage of the hydrazine N-N bond using SmI2 is also demonstrated.
• [EN] DEPROTECTION OF BOC-PROTECTED COMPOUNDS<br/>[FR] DÉPROTECTION DE COMPOSÉS PROTÉGÉS PAR UN GROUPE BOC
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010142616A2

  公开（公告）日：2010-12-16

  Organic compounds having t-butyl ester or BOC carbonate protecting groups are effectively deprotected by heating in a fluorinated alcohol solution.
• A novel practical cleavage of tert-butyl esters and carbonates using fluorinated alcohols
  作者：Jason Choy、Saul Jaime-Figueroa、Teresa Lara-Jaime

  DOI：10.1016/j.tetlet.2010.02.100

  日期：2010.4

  Thermolytic cleavage of t-butyl esters and t-butyl carbonates was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvent. Thus, a practical method to cleanly convert t-butyl esters and carbonates into the corresponding carboxylic acids, decarboxylated products, or alcohols in nearly quantitative yields was developed. The product is recovered by a simple solvent evaporation. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic esters. (C) 2010 Elsevier Ltd. All rights reserved.
• Di-tert-butyl dicarbonate: a versatile carboxylating reagent
  作者：John Kallikat Augustine、Y. Arthoba Naik、Veeramani Vairaperumal、Sharmila Narasimhan

  DOI：10.1016/j.tet.2008.10.089

  日期：2009.1

  (Boc-anhydride) to provide the corresponding tert-butyl aryl acetates, di-tert-butyl aryl malonates, unsymmetrical aryl malonates and tert-butyl benzoates in high yields. This reaction represents another useful way to prepare a variety of tert-butyl carboxylates and highlights the synthetic utility of di-tert-butyl dicarbonate as a versatile carboxylating reagent.

  通过非亲核碱（LDA）生成的碳亲核试剂被有效捕集与二-叔丁基二碳酸酯（Boc-酸酐），以提供相应的叔丁基的芳基乙酸酯，二-叔丁基的芳基丙二酸酯，芳不对称丙二和叔高产率的苯甲酸丁酯。该反应表示准备各种的另一种有用的方式叔丁基羧酸盐和二-亮点的合成效用叔丁基二碳酸酯作为多功能羧试剂。