4-硝基-3-苯基丁酸乙酯 | 41441-40-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-硝基-3-苯基丁酸乙酯
• 英文名称: ethyl 4-nitro-3-phenylbutanoate
• 英文别名: 4-Nitro-3-phenyl-buttersaeureethylester
• CAS: 41441-40-1
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: YUZFCLKAFDLCLM-UHFFFAOYSA-N

物化性质

• 沸点：
  156-158 °C(Press: 1 Torr)
• 密度：
  1.162 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  4-硝基-3-苯基丁酸乙酯 在 palladium on activated charcoal 氢氧化钾 、 四丁基溴化铵 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 N-propargyl-4-phenyl-2-pyrrolidone
  参考文献：
  名称：

  Phenyl-substituted analogs of oxotremorine as muscarinic antagonists

  摘要：

  A series of phenyl-substituted analogues of the muscarinic agent oxotremorine (1) have been prepared. The new compounds (3b-11b and 9c) were assayed for antimuscarinic activity on the isolated guinea pig ileum and in intact mice. They were also evaluated for ability to inhibit the binding of the muscarinic antagonist (-)-[H-3]-N-methylscopolamine to homogenates of the rat cerebral cortex. The phenyl-substituted derivatives were devoid of intrinsic muscarinic activity. Instead, they behaved as competitive muscarinic antagonists in these assays with similar or lower affinity for muscarinic receptors than the corresponding methyl-substituted analogues. The succinimide (8b) and the pyrrolidone (3b) derivatives of 1 substituted with a phenyl group at position 1 of the butynyl chain showed the highest antimuscarinic potency with dissociation constants (K(D)) of 0.10 and 0.20-mu-M, respectively, in the ileum assay. The phenyl-substituted analogues showed an approximately 10-fold lower in vivo antimuscarinic potency than their corresponding methyl-substituted positional isomers. A correlation was observed between in vitro and in vivo potency within subsets consisting of methyl- and phenyl-substituted derivatives.

  DOI：

  10.1021/jm00080a013
• 作为产物：
  描述：

  1-苯基-2-硝基乙醇 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 4-硝基-3-苯基丁酸乙酯
  参考文献：
  名称：

  New Multicomponent Reaction for the Direct Synthesis of β-Aryl-γ-nitroesters Promoted by Hydrotalcite-Derived Mixed Oxides as Heterogeneous Catalyst

  摘要：

  A new approach based on multicomponent/domino combined reactions for the synthesis of gamma-nitroesters promoted by a mixed aluminium-magnesium oxides derived from hydrotalcite-like material was developed. Different gamma-nitroesters were synthesized in 15-95% yield using Meldrum's acid, aromatic aldehydes, nitromethane and different alcohols as reagents and solvents. The gamma-aminobutyric acid derivatives, Phenibut and Baclofen, were prepared in 63 and 61% overall yield, respectively, through a two steps synthetic strategy. A mechanistic pathway was proposed based on the gas chromatography mass spectrometry (GC-MS) and electrospray ionization mass spectrometry (ESI-MS) experiments.

  DOI：

  10.5935/0103-5053.20160175

文献信息

• Asymmetric synthesis of piperidines using the nitro-Mannich reaction☆
  作者：James C. Anderson、Eva Bouvier-Israel、Christopher D. Rundell、Xiangyu Zhang

  DOI：10.1016/j.tet.2020.131821

  日期：2021.1

  A method for the synthesis of functionalized piperidines containing 3 contiguous stereocentres in the 2-,3- and 4- positions uses a diastereoselective nitro-Mannich to control stereochemistry. The nitro-Mannich reaction between a β-aryl/heteroaryl substituted nitroalkanes and glyoxylate imine provides β-nitro-amines with good selectivity (70:30 to >95:5) for the syn, anti-diastereoisomers. Reductive

  合成在2-，3-和4-位含有3个连续立体中心的官能化哌啶的方法是使用非对映选择性硝基曼尼希来控制立体化学。一个之间的硝基-曼尼希反应β -芳基/杂芳基取代的硝基烷烃和乙醛酸亚胺提供具有良好的选择性β硝基胺（70:30至> 95：5）为顺式，反-diastereoisomers。纯化后，用BF 3 .OEt 2和Et 3 SiH进行的还原环化反应制得的十个具有不同4-芳基/杂芳基取代基的立体化学纯哌啶类化合物的收率为19-57％。
• Synthesis of β-Functionalized α,β-Unsaturated Oximes via Silylation of Nitro Compounds
  作者：Vitaly M. Danilenko、Alexander A. Tishkov、Sema L. Ioffe、Ilya M. Lyapkalo、Yury A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1055/s-2002-23539

  日期：——

  A general method for the synthesis of conjugated enoximes 2 via silylation of functionalized aliphatic nitro compounds 1 has been claborated. The configuration of obtained products has been determined by NMR spectroscopy.

  已经制定了通过官能化脂肪族硝基化合物 1 的甲硅烷基化合成共轭酶肟 2 的通用方法。所得产物的构型已通过核磁共振光谱确定。
• Rapid Synthesis of Bicyclic N-Heterocyclic Cores from N-Terminal α,β-Unsaturated Diazoketones
  作者：João Victor Santiago、Antonio C. B. Burtoloso

  DOI：10.1002/ejoc.201800239

  日期：2018.6.15

  The synthesis of bicyclic N‐heterocyclic cores from N‐terminal α,β‐unsaturated diazoketones is described. The transformation consists of a three‐step domino process that involves a one‐pot N‐deprotection, intramolecular aza‐Michael, and photochemical Wolff rearrangement sequence of reactions.

  描述了由N末端α，β-不饱和重氮酮合成双环N杂环核的方法。转化过程包括三步多米诺过程，涉及一个一锅N-脱保护，分子内氮杂迈克尔和光化学反应的Wolff重排序列。
• One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives
  作者：Fabricio F. Naciuk、Debora Z. Vargas、Caroline R. M. D'Oca、Celso C. Moro、Dennis Russowsky

  DOI：10.1039/c4nj01552e

  日期：——

  γ-Nitroesters are synthesized by theone potdomino process. GABA derivatives phenibut and baclofen were readily accessed.

  γ-硝基酯通过一锅法多米诺过程合成。GABA衍生物苯硫胺和巴克洛芬可以轻松获得。
• Intermediates for the Synthesis of 4-Substituted Proline Derivatives
  作者：Christine Willis、Stuart Crosby、Richard Sessions

  DOI：10.1055/s-0029-1219372

  日期：2010.3

  A chemoenzymatic synthesis of a series of 2-hydroxy-5-nitro-4-substituted esters is described that uses two biotransformations in a single-pot process in which a kinetic resolution/reduction occurs. The products are valuable intermediates for the preparation of 4-substituted prolines and 5-substituted 3-hydroxypiperidinones as illustrated by the preparation of (2R,4R)-4-methylproline and (3S,5R)-3-hydroxy-5-methylpiperidinone.

  描述了一种化学酶合成系列2-羟基-5-硝基-4-取代酯的过程，该过程在一个反应器中利用两种生物转化进行动力学分离/还原。所得到的产品是制备4-取代脯氨酸和5-取代3-羟基哌啶酮的宝贵中间体，如(2R,4R)-4-甲基脯氨酸和(3S,5R)-3-羟基-5-甲基哌啶酮的制备所示。