N-methoxy-N-methyl-2-(benzo[d][1,3]dioxol-5-yl)acetamide | 153277-41-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-methoxy-N-methyl-2-(benzo[d][1,3]dioxol-5-yl)acetamide
• 英文别名: 2-(1,3-benzodioxol-5-yl)-N-methoxy-N-methyl acetamide；2-benzo(1,3)dioxol-5-yl-N-methoxy-N-methylacetamide；2-(benzo[d][1,3]dioxol-5-yl)-N-methoxy-N-methylacetamide；2-(1,3-benzodioxol-5-yl)-N-methoxy-N-methylacetamide
• CAS: 153277-41-9
• 化学式: C₁₁H₁₃NO₄
• mdl: MFCD25959404
• 分子量: 223.229
• InChiKey: ZVCDSMMCVQXTQN-UHFFFAOYSA-N

物化性质

• 沸点：
  321.3±52.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、DCM

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-2-(benzo[d][1,3]dioxol-5-yl)acetamide 在 四丙基高钌酸铵 、 硼烷四氢呋喃络合物 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.17h， 生成 5-(benzo[d][1,3]dioxol-5-ylmethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  TiCl4 促进的串联羰基或亚胺加成和 Friedel-Crafts 环化：苯并稠合氧杂双环辛烷和壬烷的合成

  摘要：

  描述了苯并稠合的 8-氧杂双环 [3.2.1] 辛烷和 9-氧杂双环 [4.2.1] 壬烷衍生物的新型便捷合成方法。该反应涉及 TiCl 4介导的串联羰基或亚胺加成，然后是 Friedel-Crafts 环化，以提供这些功能化的衍生物，收率非常好，并且具有高非对映选择性。

  DOI：

  10.1021/ol300494q
• 作为产物：
  描述：

  胡椒乙酸 在 氯化亚砜 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 1.0h， 生成 N-methoxy-N-methyl-2-(benzo[d][1,3]dioxol-5-yl)acetamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel 4-thiazolylimidazoles as inhibitors of transforming growth factor-β type I receptor kinase

  摘要：

  A novel series of 4-thiazolylimidazoles was synthesized as transforming growth factor-beta (TGF-beta) type I receptor (also known as activin receptor-like kinase 5 or ALK5) inhibitors. These compounds were evaluated for their ALK5 inhibitory activity in an enzyme assay and their TGF-beta-induced Smad2/3 phosphorylation inhibitory activity in a cell-based assay. N-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1, 3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}butanamide 20, a potent and selective ALK5 inhibitor, exhibited good enzyme inhibitory activity (IC50 = 8.2 nM) as well as inhibitory activity against TGF-beta-induced Smad2/3 phosphorylation at a cellular level (IC50 = 32 nM). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.066

文献信息

• [EN] ANTIBACTERIAL COMPOUNDS AND METHODS FOR USE<br/>[FR] COMPOSÉS ANTIBACTÉRIENS ET PROCÉDÉS POUR LEUR UTILISATION
  申请人：PTC THERAPEUTICS INC

  公开号：WO2013033228A1

  公开（公告）日：2013-03-07

  The present description relates to compounds and forms and pharmaceutical compositions thereof and methods for use thereof to treat or ameliorate bacterial infections caused by wild-type and multi-drug resistant Gram-negative and Gram-positive pathogens. The present description further relates to a compound having activity toward wild-type and MDR bacteria. The present description also relates to a compound having activity against quinolone-resistant Gram-negative strains (including MDR strains) as well as antibacterial activity to MDR resistant Gram-positive pathogens (including MRSA strains).

  本描述涉及化合物、形式、以及其制药组合物，以及治疗或改善由野生型和多药耐药革兰氏阴性和革兰氏阳性病原体引起的细菌感染的方法。本描述还涉及一种对野生型和MDR细菌具有活性的化合物。本描述还涉及一种对喹诺酮耐药革兰氏阴性菌株（包括MDR菌株）具有活性以及对MDR耐药革兰氏阳性病原体（包括MRSA菌株）具有抗菌活性的化合物。
• Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds
  作者：Wen Liu、Maoping Pu、Jun He、Tinghui Zhang、Shunxi Dong、Xiaohua Liu、Yun-Dong Wu、Xiaoming Feng

  DOI：10.1021/jacs.1c05881

  日期：2021.8.4

  Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C–N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated

  烯烃的叠氮化是合成有机叠氮化物的有效方法，有机叠氮化物是有机合成中的重要结构基序。由于自由基固有的不稳定性和独特的结构，对映选择性自由基叠氮化作为安装 C-N 3键的有用策略仍然具有挑战性。在这里，我们公开了由手性N , N '-二氧化物 / Fe(OTf) 2催化的α,β-不饱和酮和酰胺的有效对映选择性自由基碳叠氮化和重氮化复合体。一系列取代的烯烃被转化为相应的α-叠氮羰基衍生物，具有良好到优异的对映选择性，有利于手性α-氨基酮、邻氨基醇和邻二胺的制备。对照实验和机理研究证明了反应过程中的自由基途径。DFT 计算表明叠氮基通过分子内五元过渡态与 Fe-N 3物种的内部氮转移到自由基中间体。
• New Six- to Eight-Membered-Ring Formation Based on the lntramolecular Endo-Mode Ring Closure of Allenyl (Substituted Phenyl)alkyl Ketones
  作者：Yoshimitsu Nagao、Woo Song Lee、Yoichi Komaki、Shigeki Sano、Motoo Shiro

  DOI：10.1246/cl.1994.597

  日期：1994.3

  Several allenyl ketones possessing an aryl group were submitted to a new intramolecular endo-mode cyclization with BF3·OEt2 or TiCl4 in CH2Cl2 to afford the corresponding 6-, 7-, and 8-membered carbocyclic products.

  在 CH2Cl2 中，用 BF3-OEt2 或 TiCl4 对几种带有芳基的烯基酮进行了新的分子内内向模式环化，得到了相应的 6、7 和 8 元碳环产物。
• Some unusual reactions of weinreb amides
  作者：Gary E. Keck、Stanton F. McHardy、Jerry A. Murry

  DOI：10.1016/s0040-4039(00)73713-0

  日期：1993.9

  Certain N-methoxy-N-methyl amides yield products of formal reduction and/or rearrangement upon exposure to tert-butyldimethylsilyl triflate and collidine or triethylamine.

  当暴露于三氟甲磺酸叔丁基二甲基甲硅烷基酯和可力丁或三乙胺时，某些N-甲氧基-N-甲基酰胺会产生形式还原和/或重排的产物。
• Thiazole derivative
  申请人：Sato Masakazu

  公开号：US20070154428A1

  公开（公告）日：2007-07-05

  A thiazolylimidazole derivative represented by the formula or a pharmaceutically acceptable salt thereof, and an ALK5 inhibitor, an therapeutic agent for alopecia or a hair growth agent having the above as an active ingredient, wherein: X 1 and X 2 are different from each other and represent a sulfur atom or a carbon atom; R 1 represents a phenyl group; a substituted phenyl group; a phenyl group condensed with a hetero aromatic ring; a pyridyl group; or a pyridyl group condensed with a hetero aromatic ring; R 2 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms substituted with 1 to 5 halogen atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyl group having 1 to 5 carbon atoms, or a hydroxyalkyl group having 1 to 6 carbon atoms, A represents a group which is represented by the formula. The present invention provides an inhibitory substance against ALK5 which is a TGF-β type I receptor and provides a hair growth stimulant or a hair growth agent based on its novel activities.

  一种由以下公式表示的噻唑咪唑衍生物或其药学上可接受的盐，以及ALK5抑制剂，作为治疗脱发或促进头发生长的活性成分。其中：X1和X2不同，分别表示硫原子或碳原子；R1表示苯基；取代苯基；与杂环芳香环融合的苯基；吡啶基；或与杂环芳香环融合的吡啶基；R2表示氢原子，卤素原子，具有1到6个碳原子的烷基，具有1到6个碳原子的烷基，该烷基被1到5个卤素原子取代，具有1到6个碳原子的烷氧基，具有1到5个碳原子的烷酰基或具有1到6个碳原子的羟基烷基；A表示由以下公式表示的基团。本发明提供了一种抗TGF-β类型I受体ALK5的抑制物质，并基于其新颖的活性提供了一种促进头发生长的刺激剂或头发生长剂。