3-(1H-吲哚-3-基)-2-硝基丙酸乙酯 | 63971-99-3

• 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: 3-(1H-吲哚-3-基)-2-硝基丙酸乙酯
• 英文名称: ethyl 3-(1H-indol-3-yl)-2-nitropropanoate
• 英文别名: 3-indol-3-yl-2-nitro-propionic acid ethyl ester；3-Indol-3-yl-2-nitro-propionsaeure-aethylester；α-Nitro-β-(3-indolyl)-propionsaeureethylester；β-(Indolyl-3)-α-nitropropionsaeureethylester；Ethyl-α-nitro-β-(3-indolyl)-propionat
• CAS: 63971-99-3
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: TWFYELOBENMNHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(1H-吲哚-3-基)-2-硝基丙酸乙酯 在 盐酸 、 sodium hydroxide 、 乙醇 、 镍 作用下， 100.0 ℃ 、10.3 MPa 条件下， 生成 色胺
  参考文献：
  名称：

  The Chemistry of Nitroacetic Acid and its Esters. III. The Synthesis of Tryptamine from Ethyl-α-nitro-β-(3-indole)-propionate¹

  摘要：

  DOI：

  10.1021/ja01626a092
• 作为产物：
  描述：

  diethyl (indol-3'-ylmethyl)nitromalonate 在 乙醚 、 乙醇 、 sodium ethanolate 作用下， 生成 3-(1H-吲哚-3-基)-2-硝基丙酸乙酯
  参考文献：
  名称：

  The Chemistry of Nitroacetic Acid and its Esters. II. The Synthesis of Ethyl α-Nitro-β-(3-indole)-propionate from Gramine and Ethyl Nitromalonate

  摘要：

  DOI：

  10.1021/ja01177a039

文献信息

• Aryl Substituted Indoles and Their Use as Blockers of Sodium Channels
  申请人：Kyle Donald J.

  公开号：US20130296281A1

  公开（公告）日：2013-11-07

  The invention relates to aryl and heteroaryl substituted compounds of Formula (I), and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein G, R 1 , and Z 1 -Z 5 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula (I) to treat a disorder responsive to the blockade of sodium channels. Compounds of the present invention are especially useful for treating pain.

  本发明涉及具有式（I）的芳基和杂芳基取代化合物，以及其药学上可接受的盐、前药或溶剂化物，其中G、R1和Z1-Z5如规范中所述。本发明还涉及利用式（I）的化合物治疗对钠通道阻滞有响应的疾病。本发明的化合物特别适用于治疗疼痛。
• Efficient Preparation of 2-Indolyl-1-nitroalkane Derivatives Employing Nitroalkenes as Versatile Michael Acceptors:  New Practical Linear Approach to Alkyl 9<i>H</i>-β-Carboline-4-carboxylate
  作者：Giuseppe Bartoli、Marcella Bosco、Sandra Giuli、Arianna Giuliani、Laura Lucarelli、Enrico Marcantoni、Letizia Sambri、Elisabetta Torregiani

  DOI：10.1021/jo048776w

  日期：2005.3.1

  The combination of cerium(III) chloride heptahydrate and sodium iodide supported on silica gel is known to promote Michael-type additions. Continuing our work on solvent-free conditions, the CeCl3·7H2O−NaI−SiO2 system catalyzes the addition of a variety of indoles and nitroalkenes, giving 2-indolyl-1-nitroalkane derivatives in good yields. Development of this method has resulted in a new protocol for

  已知负载在硅胶上的七水合氯化铈（III）和碘化钠可促进迈克尔型添加。在无溶剂条件下继续我们的工作，CeCl 3 ·7H 2 O-NaI-SiO 2系统催化添加各种吲哚和硝基烯烃，从而以高收率得到2-吲哚基-1-硝基烷烃衍生物。该方法的发展为合成4-取代的β-咔啉提供了新的方法。
• An efficient one-pot reaction of indoles, nitroacetate, and paraformaldehyde for the synthesis of tryptophan derivatives
  作者：Yong Sui、Li Liu、Jun-Ling Zhao、Dong Wang、Yong-Jun Chen

  DOI：10.1016/j.tetlet.2007.04.002

  日期：2007.5

  An efficient method for the synthesis of tryptophan analogues has been developed via one-pot reaction of commercial available indoles, ethyl nitroacetate, and paraformaldehyde in the presence of molecular sieves. The reaction provided tryptophan nitro-precursors in moderate to good yields, which were further converted to α-hydroxymethylated tryptophan derivatives catalyzed by DABCO in high yields.

  通过在分子筛的存在下市售吲哚，硝基乙酸乙酯和多聚甲醛的一锅反应，已经开发了一种合成色氨酸类似物的有效方法。该反应以中等至良好的产率提供了色氨酸硝基前体，然后将其进一步转化为由DABCO催化的高产率的α-羟甲基化的色氨酸衍生物。
• Syntheses of 1,3-disubstituted N-oxy-β-carbolines by the Pictet-Spengler reactions of N-oxy-tryptophan and -tryptamine derivatives
  作者：Pedro H.H. Hermkens、Jan H. van Maarseveen、Peter L.H.M. Cobben、Harry C.J. Ottenheijm、Chris G. Kruse、Hans W. Scheerent

  DOI：10.1016/s0040-4020(01)81366-1

  日期：1990.1
• Coupling of activated esters to gramines in the presence of ethyl propiolate under mild conditions
  作者：David T. Jones、Gerald D. Artman、Robert M. Williams

  DOI：10.1016/j.tetlet.2006.12.016

  日期：2007.2

  The coupling of activated esters to gramine derivatives is described using ethyl propiolate. A series of substrates have been prepared using these mild conditions to provide a scope and limitations for this methodology. (c) 2007 Elsevier Ltd. All rights reserved.