1-(2-硝基苯基)-L-脯氨酸 | 31981-54-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1-(2-硝基苯基)-L-脯氨酸
• 英文名称: (S)-N-(2-nitrophenyl)proline
• 英文别名: 1-(2-Nitrophenyl)-L-proline；(2S)-1-(2-nitrophenyl)pyrrolidine-2-carboxylic acid
• CAS: 31981-54-1
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: MVJZGJIDVGGPCQ-JTQLQIEISA-N

物化性质

• 熔点：
  116-118 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  447.8±40.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(2-硝基苯基)-L-脯氨酸 在 铁粉 、 溶剂黄146 作用下， 反应 3.0h， 生成 -1,2,3四氢吡咯并[1,2-A]喹喔-4(5H)-酮
  参考文献：
  名称：

  Tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines: vascular smooth muscle relaxants and antihypertensive agents

  摘要：

  A series of tetrahydropyrrolo[1,2-a]quinoxalines and tetrahydropyrrolo[1,2-a]pyrido[3,2-a]pyrazines were synthesized and tested for their ability to relax K+-depolarized aortic smooth muscle and antihypertensive activity. It was shown that compounds producing the most relaxation of aortic smooth muscle (5-[2,6-dimethoxyphenyl)methyl]-1,2,3,3a-tetrahydropyrrolo[1,2-a] quinoxalin-4(5H)-one and 5-[(2,6-dimethoxyphenyl)methyl]-5,6,6a,7,8,9-hexahydropyrrolo[1,2- a] pyrazine, 10 and 19, respectively) demonstrated the least hypotensive activity. Those compounds that were the most effective hypotensive agents (6a,7,8,9-tetrahydro-5-(phenylmethyl)pyrido[3,2-a]pyrrolo[1,2-a]++ +pyrazin- 6(5H)-one and 6a,7,8,9-tetrahydro-5-(4-pyridinylmethyl)pyrido[3,2-e]pyrrolo [1,2-a]pyrazin-6(5H)-one, 12 and 13, respectively) displayed little vascular smooth muscle relaxant activity.

  DOI：

  10.1021/jm00378a039
• 作为产物：
  描述：

  1-溴-2-硝基苯 、 L-脯氨酸 在 copper(l) iodide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以90%的产率得到1-(2-硝基苯基)-L-脯氨酸
  参考文献：
  名称：

  Copper-catalyzed C–N coupling reactions of aryl halides with α-amino acids under focused microwave irradiation

  摘要：

  We have developed an efficient method for the preparation of enantiopure N-aryl-alpha-amino acids via copper-catalyzed N-arylation of alpha-amino acids and aryl halides under microwave irradiation. This protocol only needs less than 30 min to obtain the products, which are far superior to those obtained under conventional heating. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.122

文献信息

• Biphenyl derivatives and drug composition
  申请人：Wakamoto Pharmaceutical Co., Ltd.

  公开号：US06225306B1

  公开（公告）日：2001-05-01

  A biphenyl derivative represented by the following general formula (1) and a pharmaceutically acceptable salt thereof: [In the formula (1), A represents a single bond, —CH2—, —CO—, —CS— or —SO2—; B represents a single bond or —CH2—; R1 represents a hydrogen atom, —OH, —NR11R12 (wherein R11 and R12 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), —OCOCH3, or a halogen atom; R2 represents a hydrogen atom or R1 and R2 form a group ═O together; R3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; provided that in the formula, the absolute configuration of the position a may be either R or S]. The compound of the present invention has considerably high safety and efficacy and is useful as, in particular, a vasopressin receptor antagonist.

  由以下一般式（1）表示的联苯衍生物和其药学上可接受的盐：[在式（1）中，A代表单键，—CH2—，—CO—，—CS—或—SO2—；B代表单键或—CH2—；R1代表氢原子，—OH，—NR11R12（其中R11和R12各自独立地代表一个氢原子或具有1至4个碳原子的烷基基团），—OCOCH3或卤素原子；R2代表氢原子或R1和R2共同形成一个羟基；R3代表氢原子或具有1至4个碳原子的烷基基团；在该式中，位置a的绝对构型可以是R或S]。本发明的化合物具有相当高的安全性和有效性，并且特别适用作为抗利尿激素受体拮抗剂。
• Iron- or Zinc-Mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones
  作者：Dazhi Li、Thierry Ollevier

  DOI：10.1002/ejoc.201801639

  日期：2019.2.14

  A general and efficient synthesis of dihydroquinoxalinones has been developed. The reductive cyclization of N‐(o‐nitroaryl)amino esters was performed by using iron and zinc metal under mild conditions in a water/ethyl acetate mixture. The final products were obtained in moderate to high yields and high enantiomeric purity.

  已经开发了二氢喹喔啉酮的通用且有效的合成方法。N-（邻-硝基芳基）氨基酯的还原环化反应是在水/乙酸乙酯混合物中，在温和条件下使用铁和锌金属进行的。以中等至高产率和高对映体纯度获得最终产物。
• Synthesis of Tri- and Tetracyclic Condensed Quinoxalin-2-ones Fused Across the C-3−N-4 Bond
  作者：Roberto Chicharro、Sonia de Castro、José L. Reino、Vicente J. Arán

  DOI：10.1002/ejoc.200300028

  日期：2003.6

  studied the preparation of some fused quinoxalinones by Stevens rearrangement of a spiro-quinoxaline-derived ammonium ylide or by treatment of N-(2,4-dinitrophenyl)- and N-(2-nitrophenyl)imino acids with different reducing agents. We have reinvestigated and clarified some related processes found in the literature starting from imino acids derivatives. Additional reactions of the fused quinoxalinones

  我们研究了通过史蒂文斯重排螺-喹喔啉衍生的叶立德铵或用不同的还原剂处理 N-(2,4-二硝基苯基)-和 N-(2-硝基苯基) 亚胺酸来制备一些稠合喹喔啉酮。我们重新研究并澄清了一些从亚氨基酸衍生物开始的文献中发现的相关过程。还报道了稠合喹喔啉酮的其他反应，以及一些容易获得的 1-芳基二氢吲哚-2-羧酸到相应的 1-芳基吲哚的有用脱氢/脱羧反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Internal Chelation-Guided Regio- and Stereoselective Pauson-Khand-Type Reaction by Chiral Rhodium(I) Catalysis
  作者：Dong Eun Kim、Sang Hee Park、Yun Hee Choi、Sueg-Geun Lee、Dohyun Moon、Jungju Seo、Nakcheol Jeong

  DOI：10.1002/asia.201100271

  日期：2011.8.1

  Touch, Pauson, engage: To explain the unique superior reactivity and stereoselectivity of O‐tethered enynes in asymmetric Pauson–Khand type reaction (APKR) than their congeners, the internal‐chelation to metal of oxygen atom of the substrate in the transition state was proposed. This proposition was well supported by APKR with several different substrates.

  接触，鲍森，参与：为了解释在非对称鲍森-肯德型反应（APKR）中，O系链烯的独特反应性和立体选择性优于同类物，在过渡态下，底物对氧原子金属的内部螯合是建议的。APKR在几种不同的基材上很好地支持了这一主张。
• <i>N</i>-(2-Nitrophenyl)proline:  An Intramolecular Hydrogen Bond Forming Reagent for the Determination of the Absolute Configuration of Primary Amines
  作者：Hee Choon Ahn、Kihang Choi

  DOI：10.1021/ol7017455

  日期：2007.9.1

  N-(2-Nitrophenyl)proline (2-NPP) amides of primary amines have a conformational preference for intramolecular hydrogen bonding. Because of the strong and selective anisotropic effects on the amine substituents, the absolute configuration of alpha-chiral primary amines can be assigned by comparing the 1H chemical shifts of diastereomeric 2-NPP amides.

  伯胺的N-（2-硝基苯基）脯氨酸（2-NPP）酰胺对于分子内氢键具有构象偏爱。由于对胺取代基的强烈且选择性的各向异性作用，可以通过比较非对映体2-NPP酰胺的1H化学位移来确定α-手性伯胺的绝对构型。