N-[2-(4-methoxyphenyl)-2-oxoethyl]methanesulfonamide | 1266682-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[2-(4-methoxyphenyl)-2-oxoethyl]methanesulfonamide
• CAS: 1266682-60-3
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: ADFZPBQVEXRBIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(4-methoxyphenyl)-2-oxoethyl]methanesulfonamide 、 ethyl 2-acetoxy-3-nitro-4-phenylbut-3-enoate 在 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以86%的产率得到ethyl 2-(4-methoxybenzoyl)-5-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Cascade reaction for 3-pyrrolines and pyrroles from nitroallylic acetates and N-mesyl 2-aminoethanones

  摘要：

  Cascade reactions of nitroallylic acetates with methanesulfonyl 2-aminoethanones affords either the 3-pyrrolines or the pyrroles in one pot depending on reaction solvents and temperature. A possible mechanism for the entire sequence is proposed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.045

文献信息

• Exploring Natural Product Chemistry and Biology with Multicomponent Reactions. 5. Discovery of a Novel Tubulin-Targeting Scaffold Derived from the Rigidin Family of Marine Alkaloids
  作者：Liliya V. Frolova、Igor V. Magedov、Anntherese E. Romero、Menuka Karki、Isaiah Otero、Kathryn Hayden、Nikolai M. Evdokimov、Laetitia Moreno Y. Banuls、Shiva K. Rastogi、W. Ross Smith、Shi-Long Lu、Robert Kiss、Charles B. Shuster、Ernest Hamel、Tania Betancourt、Snezna Rogelj、Alexander Kornienko

  DOI：10.1021/jm400711t

  日期：2013.9.12

  We developed synthetic chemistry to access the marine alkaloid rigidins and over 40 synthetic analogues based on the 7-deazaxanthine, 7-deazaadenine, 7-deazapurine, and 7-deazahypoxanthine skeletons. Analogues based on the 7-deazahypoxanthine skeleton exhibited nanomolar potencies against cell lines representing cancers with dismal prognoses, tumor metastases, and multidrug resistant cells. Studies

  我们开发了合成化学以获取海洋生物碱硬质素和 40 多种基于 7-脱氮黄嘌呤、7-脱氮杂腺嘌呤、7-脱氮嘌呤和 7-脱氮次黄嘌呤骨架的合成类似物。基于 7-脱氮次黄嘌呤骨架的类似物对代表预后不佳的癌症、肿瘤转移和多药耐药细胞的细胞系表现出纳摩尔级的效力。旨在阐明 7-脱氮杂次黄嘌呤在癌细胞中的作用模式的研究表明，它们在活 HeLa 细胞中抑制体外微管蛋白聚合和微管紊乱。评估 7-脱氮杂次黄嘌呤对 [ 3]结合作用的实验H]秋水仙碱到微管蛋白鉴定出微管蛋白上的秋水仙碱位点是癌细胞中这些化合物最可能的靶点。由于许多微管靶向化合物在临床上已成功用于抗癌，我们相信以 7-脱氮次黄嘌呤刚性类似物为代表的新化学类抗微管蛋白药物具有作为新抗癌药物的巨大潜力。
• One-Pot Multicomponent Synthesis of Diversely Substituted 2-Aminopyrroles. A Short General Synthesis of Rigidins A, B, C, and D
  作者：Liliya V. Frolova、Nikolai M. Evdokimov、Kathryn Hayden、Indranil Malik、Snezna Rogelj、Alexander Kornienko、Igor V. Magedov

  DOI：10.1021/ol103149b

  日期：2011.3.4

  Privileged medicinal scaffolds based on the structures of tetra- and pentasubstituted 2-aminopyrroles were prepared via one-pot multicomponent reactions of structurally diverse aldehydes and N-(aryl-, hetaryl-, alkylsulfonamido)acetophenones with activated methylene compounds. This methodology was used in a four-step synthesis of alkaloids rigidins A, B, C, and Din overall yields of 61%, 58%, 60%, and 53%, respectively. Of these, rigidins B, C, and D were synthesized for the first time.
• Cascade reaction for 3-pyrrolines and pyrroles from nitroallylic acetates and N-mesyl 2-aminoethanones
  作者：Tong Chen、Nana Shao、Huajian Zhu、Boya Zhang、Hongbin Zou

  DOI：10.1016/j.tet.2013.10.045

  日期：2013.12

  Cascade reactions of nitroallylic acetates with methanesulfonyl 2-aminoethanones affords either the 3-pyrrolines or the pyrroles in one pot depending on reaction solvents and temperature. A possible mechanism for the entire sequence is proposed. (C) 2013 Elsevier Ltd. All rights reserved.