methyl 4-((tert-butoxycarbonyl)amino)furan-2-carboxylate | 1170719-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 4-((tert-butoxycarbonyl)amino)furan-2-carboxylate
• 英文别名: methyl 4-[(2-methylpropan-2-yl)oxycarbonylamino]furan-2-carboxylate
• CAS: 1170719-58-0
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: BTTOSJPNLDNHSK-UHFFFAOYSA-N

物化性质

• 沸点：
  301.2±27.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-((tert-butoxycarbonyl)amino)furan-2-carboxylate 在 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 methyl (5-((5-((2-(1H-indol-3-yl)ethyl)carbamoyl)furan-3-yl)carbamoyl)furan-3-yl)carbamate
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of proximicins A, B and C

  摘要：

  A quick and efficient synthesis and the biological evaluation of promising antitumor-antibiotics proximicins A, B and C are reported. The characteristic repetitive unit of these molecules, the methyl 4-Boc-aminofuran-2-carboxylate 15, was prepared in three synthetic steps in good yield using an optimised copper-catalysed amidation method. The proximicins were evaluated for their antitumor activity using cellular methods. Proximicin B induced apoptosis in both Hodgkin's lymphoma and T-cell leukemia cell lines and proximicin C exhibited significantly high cytotoxicity against glioblastoma and breast carcinoma cells. The proximicins were also screened against Escherichia coli, Enterococcus faecalis and several strains of methicillin-and multidrug-resistant Staphylococcus aureus. Proximicin B showed noteworthy activity against antibiotic-resistant Gram-positive cocci. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.043
• 作为产物：
  描述：

  2-糠酸甲酯 在 aluminum (III) chloride 、 copper(l) iodide 、 溴 、 potassium carbonate 、 氯化铵 、 N,N'-二甲基乙二胺 、 锌 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 26.5h， 生成 methyl 4-((tert-butoxycarbonyl)amino)furan-2-carboxylate
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of proximicins A, B and C

  摘要：

  A quick and efficient synthesis and the biological evaluation of promising antitumor-antibiotics proximicins A, B and C are reported. The characteristic repetitive unit of these molecules, the methyl 4-Boc-aminofuran-2-carboxylate 15, was prepared in three synthetic steps in good yield using an optimised copper-catalysed amidation method. The proximicins were evaluated for their antitumor activity using cellular methods. Proximicin B induced apoptosis in both Hodgkin's lymphoma and T-cell leukemia cell lines and proximicin C exhibited significantly high cytotoxicity against glioblastoma and breast carcinoma cells. The proximicins were also screened against Escherichia coli, Enterococcus faecalis and several strains of methicillin-and multidrug-resistant Staphylococcus aureus. Proximicin B showed noteworthy activity against antibiotic-resistant Gram-positive cocci. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.043

文献信息

• [EN] HERBICIDAL MALONAMIDES<br/>[FR] MALONAMIDES HERBICIDES
  申请人：BASF SE

  公开号：WO2021170464A1

  公开（公告）日：2021-09-02

  The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R1 to R9 represent groups such as hydrogen, halogen or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxyl or a linear or cyclic organic group. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

  该发明涉及式(I)的化合物，以及它们作为除草剂的用途。在该式中，R1至R9代表氢、卤素或有机基团，如烷基、烯基、炔基或烷氧基；X是键或二价基团；Y是氢、氰基、羟基或线性或环状有机基团。该发明还涉及包含这种化合物的组合物，以及将其用于控制不受欢迎的植被。
• Total Synthesis of Proximicin A−C and Synthesis of New Furan-Based DNA Binding Agents
  作者：Falko E. Wolter、Kathrin Schneider、Brian P. Davies、Elke R. Socher、Graeme Nicholson、Oliver Seitz、Roderich D. Süssmuth

  DOI：10.1021/ol901003p

  日期：2009.7.2

  The total synthesis of the natural occurring polyamides proximicin A−C (3−5) has been accomplished. A short and efficient synthesis of a thus far unknown 4-amino-2-furan carboxylic acid was developed. Furthermore, this unique heterocyclic γ-amino-acid was used for the synthesis of a new class of AT-selective DNA-binding agents derived from the natural products combining structural features of the proximicins

  天然存在的聚酰胺的总合成proximicin A-C（3 - 5）已经完成。开发了一种短而有效的迄今未知的4-氨基-2-呋喃羧酸的合成方法。此外，这种独特的杂环γ-氨基酸还用于合成由天然产物衍生的新型AT选择性DNA结合剂，这些结合了Proximicin的结构特征与已知的与DNA结合的天然产物netropsin的结构特征（1）和间他霉素（2）。
• [EN] TETRAHYDROTHIOPHENE-BASED GABA AMINOTRANSFERASE INACTIVATORS<br/>[FR] INACTIVATEURS DE LA GABA AMINOTRANSFÉRASE À BASE DE TÉTRAHYDROTHIOPHÈNE
  申请人：UNIV NORTHWESTERN

  公开号：WO2016145082A1

  公开（公告）日：2016-09-15

  Tetrahydrothiophene and related heterocyclic analogs and related methods for GABA aminotransferase inactivation.

  硫代四氢噻吩及其相关杂环类似物以及相关的GABA氨基转移酶失活方法。
• Synthesis of (±)-8-Oxa-3-azabicyclo[3.2.1]octan-2-thione and (±)-2-Oxa-5-azabicyclo[2.2.1]heptan-6-thione: Potential Synthons for the Preparation of Novel Heteroaryl-Annulated Bicyclic Morpholines
  作者：Daniel Walker、Donn Wishka、Paul Beagley、Gemma Turner、Nicola Solesbury

  DOI：10.1055/s-0030-1258464

  日期：2011.4

  The bridged bicyclic morpholinethiones (±)-8-oxa-3-azabicyclo[3.2.1]octane-2-thione and (±)-2-oxa-5-azabicyclo[2.2.1]heptane-6-thione have been prepared in five and eight steps, respectively. Both compounds were derived from a respective requisite cis-disubstituted tetrahydrofuran, which was stereoselectively prepared via hydrogenation of the corresponding disubstituted furan derivatives. stereoselective

  制备了桥联双环吗啉乙硫酮（±）-8-氧杂-3-氮杂双环[3.2.1]辛烷-2-硫酮和（±）-2-氧杂-5-氮杂双环[2.2.1]庚烷-6-硫酮分五个步骤和八个步骤。两种化合物均来自各自必需的顺式-二取代的四氢呋喃，其是通过氢化相应的二取代的呋喃衍生物而立体选择性地制备的。 立体选择性合成-杂环-双环化合物-呋喃-加氢
• Tetrahydrothiophene-based GABA Aminotransferase Inactivators
  申请人：Northwestern University

  公开号：US20160264544A1

  公开（公告）日：2016-09-15

  Tetrahydrothiophene and related heterocyclic analogs and related methods for GABA aminotransferase inactivation.

  四氢噻吩及其相关杂环类似物和相关方法用于GABA氨基转移酶的失活。