3-(2-硝基-苯基)-丙酸乙酯 | 66757-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(2-硝基-苯基)-丙酸乙酯
• 中文别名: 3-(2-硝基苯基)丙酸乙酯
• 英文名称: 2-nitro-benzenepropanoic acid ethyl ester
• 英文别名: ethyl 3-(2-nitrophenyl)propanoate；ethyl o-nitrophenylpropionate；3-(2-nitro-phenyl)-propionic acid ethyl ester；3-(2-Nitro-phenyl)-propionsaeure-aethylester；Aethyl-o-nitrohydrocinnamat
• CAS: 66757-87-7
• 化学式: C₁₁H₁₃NO₄
• mdl: MFCD07772951
• 分子量: 223.229
• InChiKey: NXPDBIQALSQRCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  3-(2-硝基-苯基)-丙酸乙酯 在 18-冠醚-6 、 sodium 、 铁粉 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醚 、 溶剂黄146 、 二甲基亚砜 、 paraffin oil 为溶剂， 反应 21.67h， 生成 2-isopropyl-2H-pyrrolo[3,4-c]quinolin-4(5H)-one
  参考文献：
  名称：

  Discovery and Pharmacological Profile of New 1H-Indazole-3-carboxamide and 2H-Pyrrolo[3,4-c]quinoline Derivatives as Selective Serotonin 4 Receptor Ligands

  摘要：

  Since the discovery of the serotonin 4 receptor (5-HT4R), a large number of receptor ligands have been studied. The safety concerns and the lack of market success of these ligands have mainly been attributed to their lack of selectivity. In this study we describe the discovery of N-[(4- piperidinyl)methyl]-1H-indazole-3-carboxamide and 4-[(4-piperidinyl)methoxy]-2H-pyrrolo[3,4-c]quinoline derivatives as new 5-HT4R ligands endowed with high selectivity over the serotonin 2A receptor and human ether-a-go-go-related gene potassium ion channel. Within these series, two molecules (11ab and 12g) were identified as potent and selective 5-HT4R antagonists with good in vitro pharmacokinetic properties. These compounds were evaluated for their antinociceptive action in two analgesia animal models. 12g showed a significant antinociceptive effect in both models and is proposed as an interesting lead compound as a 5-HT4R antagonist with analgesic action.

  DOI：

  10.1021/jm300573d
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉 、 乙醇 在 双氧水 、 ortho-tungstic acid 作用下， 反应 24.0h， 以82%的产率得到3-(2-硝基-苯基)-丙酸乙酯
  参考文献：
  名称：

  使用可循环利用的钨催化剂，通过C–N键裂解，对未应变的苯并环胺进行破坏性的双官能化

  摘要：

  以H 2 WO 4为催化剂，H 2 O 2为氧化剂，我们在本文中报道了在未应变的苯并环胺中C–N键的解构二官能化，可同时生成酯基和硝基。初步的机理研究表明，相应的异羟肟酸是该转化的关键中间体。重要的是，利用这种转化，我们实现了一种有趣的方法，将喹啉环缩为吲哚，这是杂芳族体系中支架跳跃的一个例子。

  DOI：

  10.1039/c9ob00693a

文献信息

• Base directed palladium catalysed Heck arylation of acrolein diethyl acetal in water
  作者：Walid Al-Maksoud、Stéphane Menuel、Mohamad Jahjah、Eric Monflier、Catherine Pinel、Laurent Djakovitch

  DOI：10.1016/j.apcata.2013.10.004

  日期：2014.1

  The selective Heck arylation of acrolein diethyl acetal catalysed by [Pd(NH3)4]Cl2 in the presence of RAME-β-CD in water as solvent is described. Depending on the base (i.e. NaOAc or HN(i-Pr)2) good to high selectivity's towards, respectively, the cinnamaldehydes 2 or the 3-arylpropionic esters 1 were achieved. The results support that depending on the base different palladium intermediate complexes

  描述了在存在RAME-β-CD的水中作为溶剂的[Pd（NH 3）4 ] Cl 2催化的丙烯醛乙缩醛的选择性Heck芳基化。取决于对肉桂醛2或3-芳基丙酸酯1分别具有良好至高选择性的碱（即NaOAc或HN（i- Pr）2）。结果支持了根据碱形成了不同的钯中间体配合物。使用NaOAc，优先生成[ArPdX（H 2 O）2 ]}复合物，得到肉桂醛2。另一方面，在HN（i -Pr）存在下如图2所示，将产生L型配体[ArPdX（HN（i -Pr ）2（H 2 O）]或[ArPdX（HN（i -Pr ）2（HN（i -Pr）2））]，从而导致在形成3-芳基丙酸酯的1。在过去，协调胺参与很可能是通过分子内形成酯的顺式β-H的消除。
• [EN] COMPOUND WITH SEROTONINERGIC ACTIVITY, PROCESS FOR PREPARING IT AND PHARMACEUTICAL COMPOSITION COMPRISING IT<br/>[FR] COMPOSÉ PRÉSENTANT UNE ACTIVITÉ SÉROTONINERGIQUE, SON PROCÉDÉ DE FABRICATION ET COMPOSITION PHARMACEUTIQUE LA COMPRENANT
  申请人：ACRAF

  公开号：WO2010012611A1

  公开（公告）日：2010-02-04

  Compound of formula (I) in which R1, R2 and R3 are defined in the following description, and the pharmaceutically acceptable acid-addition or base-addition salts thereof. The invention also relates to a process and an intermediate for preparing it, and to a pharmaceutical composition comprising it. The invention also relates to the use of a novel 2H-pyrrolo[3,4-c]quinoline compound for preparing a pharmaceutical composition that is active in the treatment of disturbances of the serotoninergic system.

  化合物的化学式（I），其中R1、R2和R3在以下描述中定义，并其药学上可接受的酸加合物或碱加合物盐。本发明还涉及用于制备该化合物的过程和中间体，以及包含它的药物组合物。本发明还涉及使用一种新型2H-吡咯并[3,4-c]喹啉化合物制备对5-羟色胺系统紊乱治疗有效的药物组合物。
• Rearrangement of 4-acetoxy-2H-1,4-benzoxazin-3(4H)-one.
  作者：YUICHI HASHIMOTO、TAKAYOSHI ISHIZAKI、KOICHI SHUDO、TOSHIHIKO OKAMOTO

  DOI：10.1248/cpb.31.3891

  日期：——

  4-Acetoxy-2H-1, 4-benzoxazin-3 (4H)-one (3) undergoes rearrangement or nucleophilic attack to give 2-, 5-, 6-, and 7-substituted derivatives of the benzoxazinone according to the reaction conditions. The formation of 5- and 7-substituted products was interpreted in terms of nucleophilic attack on the cation (14) formed by the heterolysis of the N-O bond of 3. For the formation of 6-substituted derivatives of the benzoxazinone, participation of the oxygen atom at position 1 of the benzoxazinone (that is, formation of an oxonium ion, 18) is important. A possible mechanism for the formation of 2-substituted products also involves an oxonium ion (19). These novel aspects of acetoxybenzoxazinone chemistry may contribute to an understanding of the mechanism of the actions of the prohibitins in cereal plants.

  4-乙酰氧基-2H-1, 4-苯并恶嗪-3 (4H)-酮(3)根据反应条件进行重排或亲核攻击，得到苯并恶嗪酮的2-、5-、6-和7-取代衍生物。 5-和7-取代产物的形成被解释为对由3的N-O键杂解形成的阳离子(14)的亲核攻击。对于苯并恶嗪酮的6-取代衍生物的形成，氧的参与苯并恶嗪酮 1 位原子（即形成氧鎓离子 18）很重要。形成 2-取代产物的一个可能机制还涉及氧鎓离子 (19)。乙酰氧基苯并嗪酮化学的这些新颖方面可能有助于理解谷类植物中抑制素的作用机制。
• COMPOUND WITH SEROTONINERGIC ACTIVITY, PROCESS FOR PREPARING IT AND PHARMACEUTICAL COMPOSITION COMPRISING IT
  申请人：Alisi Maria Alessandra

  公开号：US20110160201A1

  公开（公告）日：2011-06-30

  Compound of formula (I) in which R1, R2 and R3 are defined in the following description, and the pharmaceutically acceptable acid-addition or base-addition salts thereof. The invention also relates to a process and an intermediate for preparing it, and to a pharmaceutical composition comprising it. The invention also relates to the use of a novel 2H-pyrrolo[3,4-c]quinoline compound for preparing a pharmaceutical composition that is active in the treatment of disturbances of the serotoninergic system.

  公式（I）的复合物，其中R1、R2和R3的定义如下所述，并且其药学上可接受的酸加成物或碱加成物盐。本发明还涉及一种制备它的过程和中间体，以及包含它的制药组合物。本发明还涉及使用一种新的2H-吡咯并[3,4-c]喹啉化合物制备具有治疗5-羟色胺系统紊乱活性的制药组合物。
• Compound with serotoninergic activity, process for preparing it and pharmaceutical composition comprising it
  申请人：Alisi Maria Alessandra

  公开号：US08686147B2

  公开（公告）日：2014-04-01

  Compound of formula (I) in which R1, R2 and R3 are defined in the following description, and the pharmaceutically acceptable acid-addition or base-addition salts thereof. The invention also relates to a process and an intermediate for preparing it, and to a pharmaceutical composition comprising it. The invention also relates to the use of a novel 2H-pyrrolo[3,4-c]quinoline compound for preparing a pharmaceutical composition that is active in the treatment of disturbances of the serotoninergic system.

  公式(I)的化合物，其中R1、R2和R3的定义如下所述，并且其药学上可接受的酸加成物或碱加成物盐。本发明还涉及制备该化合物的过程和中间体，以及包含该化合物的药物组合物。本发明还涉及使用一种新型2H-吡咯并[3,4-c]喹啉化合物制备对5-羟色胺系统干扰具有活性的药物组合物。