methyl 4-((methoxycarbonyl)amino)benzoate | 94563-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-((methoxycarbonyl)amino)benzoate
• 英文别名: 4-methoxycarbonylamino-benzoic acid methyl ester；(4-Methoxycarbonyl-phenyl)-carbamidsaeure-methylester；4-Methoxycarbonylamino-benzoesaeure-methylester；Methyl 4-(methoxycarbonyl)aminobenzoate；methyl 4-(methoxycarbonylamino)benzoate
• CAS: 94563-12-9
• 化学式: C₁₀H₁₁NO₄
• mdl: MFCD00555592
• 分子量: 209.202
• InChiKey: HIZGDILIYUDXBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-((methoxycarbonyl)amino)benzoate 在 sodium hydroxide 作用下， 反应 8.0h， 以54%的产率得到4-[(methoxycarbonyl)amino]benzoic acid
  参考文献：
  名称：

  Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

  摘要：

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

  DOI：

  10.1021/jm970479e
• 作为产物：
  描述：

  4-氨基苯甲酸甲酯 在 氯苯 作用下， 生成 methyl 4-((methoxycarbonyl)amino)benzoate
  参考文献：
  名称：

  Siefken, Justus Liebigs Annalen der Chemie, 1949, vol. 562, p. 75,1114

  摘要：

  DOI：

文献信息

• Synthesis of Oxazolidinones by a Hypervalent Iodine Mediated Cyclization of <i>N</i> ‐Allylcarbamates
  作者：Mirdyul Das、Arantxa Rodríguez、Pui Kin Tony Lo、Wesley J. Moran

  DOI：10.1002/adsc.202001451

  日期：2021.3.16

  The preparation of oxazolidinones by the hypervalent iodine mediated cyclization of allylcarbamates is described. A versatile range of substrates can be converted into substituted oxazolidinones primed for further transformations. Derivatization of the products at both ends is demonstrated. A preliminary attempt at the enantioselective formation of an oxazolidinone using a chiral iodane is also presented

  描述了通过高价碘介导的烯丙基氨基甲酸酯的环化制备恶唑烷酮。可以将多种底物转化为准备用于进一步转化的取代的恶唑烷酮。说明了两端产品的衍生化。还提出了使用手性碘对映体形成恶唑烷酮的初步尝试。
• Electrochemical Hofmann rearrangement mediated by NaBr: practical access to bioactive carbamates
  作者：Lijun Li、Mengyu Xue、Xin Yan、Wenmin Liu、Kun Xu、Sheng Zhang

  DOI：10.1039/c8ob01059e

  日期：——

  An electrochemical Hofmann rearrangement is reported. With the mediation of NaBr, highly corrosive and toxic halogens are avoided. Moreover, this efficient and green approach is well compatible with a broad range of amides, including several commercial medicine derivatives, and provides direct access to synthetically useful carbamates. The synthetic utility of this method is also demonstrated by the

  据报道电化学霍夫曼重排。在NaBr的介导下，避免了高度腐蚀性和剧毒的卤素。而且，这种有效且绿色的方法与各种酰胺（包括几种商业药物衍生物）很好地兼容，并提供了直接用于合成有用的氨基甲酸酯的途径。15 N标记氨基甲酸酯的制备和金刚烷胺的克级合成也证明了该方法的合成效用。
• A microfluidic flow chemistry platform for organic synthesis: the Hofmann rearrangement
  作者：Alessandro Palmieri、Steven V. Ley、Kelvin Hammond、Anastasios Polyzos、Ian R. Baxendale

  DOI：10.1016/j.tetlet.2009.02.059

  日期：2009.7

  We report on the use of commercially available chemical microreactors to effect the Hofmann rearrangement of aromatic amides to the corresponding carbamates.

  我们报道了使用可商购的化学微型反应器来实现霍夫曼重排芳族酰胺到相应的氨基甲酸酯。
• Substituted benzene derivatives useful as neuraminidase inhibitors
  申请人：BioCryst Pharmaceuticals, Inc.

  公开号：US05602277A1

  公开（公告）日：1997-02-11

  A compound of the Formula (I): ##STR1## or pharmaceutically-suitable salts or prodrug forms thereof, wherein: n is 0-1; m is 0; p is 0-1; R.sup.1 is --CO.sub.2 H; R.sup.2 is selected from the group consisting of H, --OH, and --NH.sub.2 ; R.sup.3 is H; R.sup.4 is --C(O)NHR.sup.8 ; R.sup.5 is --NHC(R.sup.6)NH.sub.2 R.sup.6 is selected from the group consisting of .dbd.NH, .dbd.NOH, .dbd.NCN, .dbd.O, and .dbd.S; and R.sup.8 is selected from the group consisting of C.sub.1 -C.sub.4 linear or branched alkyl substituted with 0-3 halogens on each carbon.

  化合物的化学式（I）：##STR1##或其药用盐或前药形式，其中：n为0-1；m为0；p为0-1；R.sup.1为--CO.sub.2 H；R.sup.2选自H、--OH和--NH.sub.2的组；R.sup.3为H；R.sup.4为--C（O）NHR.sup.8；R.sup.5为--NHC（R.sup.6）NH.sub.2 R.sup.6选自.dbd.NH、.dbd.NOH、.dbd.NCN、.dbd.O和.dbd.S的组；R.sup.8选自每个碳上取代有0-3卤素的C.sub.1-C.sub.4直链或支链烷基的组。
• Zr-MOF-808@MCM-41 catalyzed phosgene-free synthesis of polyurethane precursors
  作者：Sergio Rojas-Buzo、Pilar García-García、Avelino Corma

  DOI：10.1039/c8cy02235f

  日期：——

  nanocrystals within the mesoporous material MCM-41. A superior catalytic performance of the Zr-MOF-808@MCM-41 is demonstrated that together with increased stability stands out as an advantageous heterogeneous catalyst for polyurethane production. In situ FTIR studies have allowed a better understanding of the reaction pathway at the molecular level when the active MOF catalyst is present.

  在这项工作中，提出了一种催化方法，可使用碳酸二甲酯代替光气从芳族胺合成芳族氨基甲酸酯，这是一种绿色安全的反应过程。据报道，微晶Zr-MOF-808是一种活性和高效的多相催化剂，可在温和的反应条件下以接近定量的收率选择性地对苯胺和工业上相关的芳族二胺进行氨甲酰化反应。我们已经在介孔材料MCM-41中完成了良好分散的Zr-MOF-808纳米晶体的选择性生长。Zr-MOF-808 @ MCM-41具有优异的催化性能，证明其具有更高的稳定性，是聚氨酯生产中一种有利的多相催化剂。原位 当存在活性MOF催化剂时，FTIR研究可以更好地理解分子水平上的反应途径。