isopropyl 2-(4-nitrophenyl)acetate | 99855-94-4

• 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: isopropyl 2-(4-nitrophenyl)acetate
• 英文别名: (4-nitro-phenyl)-acetic acid isopropyl ester；(4-Nitro-phenyl)-essigsaeure-isopropylester；Propan-2-yl 2-(4-nitrophenyl)acetate；propan-2-yl 2-(4-nitrophenyl)acetate
• CAS: 99855-94-4
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: OSMVNJWMFJLJHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl 2-(4-nitrophenyl)acetate 在 sodium azide 、 硫酰氟 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以63 %的产率得到isopropyl 2-diazo-2-(4-nitrophenyl)acetate
  参考文献：
  名称：

  Synthesis of Diazo Compounds by Using NaN ₃ and Inexpensive SO ₂ F ₂

  摘要：

  AbstractA concise and efficient method was developed in which sodium azide (NaN3) and sulfuryl fluoride (SO2F2) were directly employed to synthesize diazo compounds with active methylene compounds. A variety of diazo compounds were produced in good to excellent yields. This protocol avoids the use of organosulfonyl azides, and features atom economy and mild reaction conditions. An alternate method for the synthesis of diazo compounds was provided.

  DOI：

  10.1002/ejoc.202200584
• 作为产物：
  描述：

  对硝基苯乙酸 、 异丙醇 在 4-二甲氨基吡啶 、 1-环已基-2-吗啉乙基碳二亚胺对甲苯磺酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 isopropyl 2-(4-nitrophenyl)acetate
  参考文献：
  名称：

  The Potential Application of Catalytic Antibodies to Protecting Group Removal: Catalytic Antibodies with Broad Substrate Tolerance

  摘要：

  A catalytic antibody was developed to selectively cleave the alcohol ester of 4-nitrophenylacetyl moiety while also tolerating a wide variety of structural variation on the alcohol portion of the molecule. The basis to the success of this study was that antibody epitope recognition was directed toward only key elements contained within the 4-nitrophenylacetyl group and not the entire haptenic molecule. This study offers the potential application of catalytic antibodies as practical reagents for the selective deprotection of complex multifunctionalized molecules possessing class similar protecting groups. Such a chemoabzymatic approach could eventually minimize synthetic complications which can arise from functional group protection in the synthesis of complex natural products.

  DOI：

  10.1021/ja00113a001

文献信息

• Visible-Light-Induced Meerwein Cascade Reactions for the Preparation of α-Aryl Esters
  作者：Teng-fei Niu、Liang Li、Bang-qing Ni、Mei-jie Bu、Chun Cai、Hui-liang Jiang

  DOI：10.1002/ejoc.201500659

  日期：2015.9

  A practical strategy has been developed for preparation of α-aryl ester derivatives by using a visible-light-induced Meerwein cascade reaction. This method uses molecular oxygen as an oxidant at room temperature without the need of hazardous reagents or harsh reaction conditions and provides a straightforward approach to pharmaceutically and synthetically useful α-aryl esters in moderate to good yields

  通过使用可见光诱导的 Meerwein 级联反应，已经开发了一种用于制备 α-芳基酯衍生物的实用策略。该方法在室温下使用分子氧作为氧化剂，不需要危险的试剂或苛刻的反应条件，并提供了一种直接的方法，可以从简单且容易获得的起始材料中以中等至良好的收率获得药学上和合成上有用的 α-芳基酯。该方案还制备了羟吲哚。
• Experiments on the <i>Chaperon</i> Effect in the Nitration of Aromatics
  作者：Paolo Strazzolini、Angelo G. Giumanini、Antonio Runcio、Massimo Scuccato

  DOI：10.1021/jo9709763

  日期：1998.2.1

  A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in alpha-position and a dilute solution of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced or tho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results mere compared with the corresponding classical nitration in H2SO4.
• Decomposition of Mixed Carboxylic-Carbonic Anhydrides^1a
  作者：THOMAS B. WINDHOLZ

  DOI：10.1021/jo01080a004

  日期：1960.10
• USE OF PARANITROPHENYLACETYL CHLORIDE FOR THE IDENTIFICATION OF ALCOHOLS, ETHERS, PHENOLS, AND AMINES¹
  作者：HENRY P. WARD、EDWARD F. JENKINS

  DOI：10.1021/jo01180a016

  日期：1945.7
• The Potential Application of Catalytic Antibodies to Protecting Group Removal: Catalytic Antibodies with Broad Substrate Tolerance
  作者：Tingyu Li、Susan Hilton、Kim D. Janda

  DOI：10.1021/ja00113a001

  日期：1995.3

  A catalytic antibody was developed to selectively cleave the alcohol ester of 4-nitrophenylacetyl moiety while also tolerating a wide variety of structural variation on the alcohol portion of the molecule. The basis to the success of this study was that antibody epitope recognition was directed toward only key elements contained within the 4-nitrophenylacetyl group and not the entire haptenic molecule. This study offers the potential application of catalytic antibodies as practical reagents for the selective deprotection of complex multifunctionalized molecules possessing class similar protecting groups. Such a chemoabzymatic approach could eventually minimize synthetic complications which can arise from functional group protection in the synthesis of complex natural products.