dimethyl (4-methylphenylsulfonamido)(naphthalen-2-yl)methylphosphonate | 1373284-92-4

• 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: dimethyl (4-methylphenylsulfonamido)(naphthalen-2-yl)methylphosphonate
• 英文别名: dimethyl [(2-naphthyl)(tosylamino)methyl]phosphonate；N-[[dimethoxy(oxido)phosphaniumyl]-naphthalen-2-ylmethyl]-4-methylbenzenesulfonamide
• CAS: 1373284-92-4
• 化学式: C₂₀H₂₂NO₅PS
• 分子量: 419.438
• InChiKey: NETHKFFXKGGLIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二甲基三甲硅基膦酸酯 、 苯磺酰胺,4-甲基-N-(2-萘基亚甲基)- 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以92%的产率得到dimethyl (4-methylphenylsulfonamido)(naphthalen-2-yl)methylphosphonate
  参考文献：
  名称：

  无催化剂条件下醛亚胺的氢膦酰化

  摘要：

  亚磷酸三甲基甲硅烷基酯与醛亚胺在无催化剂的条件下有效地反应，得到高产的α-氨基膦酸酯。此外，可以轻松扩大反应规模，并保持高收率。

  DOI：

  10.1002/cjoc.201200119

文献信息

• Nucleophilic Carbene-Mediated Hydrophosphonylation of Aldimines
  作者：Guang-Fen Du、Lin He、Zhi-Hua Cai、Bin Dai

  DOI：10.1055/s-0031-1289690

  日期：2012.3

  Aldimines undergo efficient hydrophosphonylation reactions with dimethyl phosphite in the presence of nucleophilic heterocyclic­ carbenes (NHCs) as organocatalysts to give the corresponding (α-aminoalkyl)phosphonates in moderate-to-excellent yields.

  阿尔基亚胺在亲核杂环氨烯（NHCs）作为有机催化剂的存在下，与二甲基磷酸酯进行高效的氢磷酸化反应，生成相应的（α-氨基烷基）磷酸酯，收率中等至优良。
• α-Sulfonamidophosphonates as new anti-mycobacterial chemotypes: Design, development of synthetic methodology, and biological evaluation
  作者：Srikant Bhagat、Metheku Supriya、Satish Pathak、Dharmarajan Sriram、Asit K. Chakraborti

  DOI：10.1016/j.bioorg.2018.09.023

  日期：2019.2

  Tuberculosis (TB) is the leading cause of death worldwide due to bacterial infection. The scarcity of effective drugs to treat the disease and the compounded problems due to the development of resistance to the available therapeutics and TB-HIV synergism drive medicinal chemists to search for new anti-Mtb chemotypes. Towards this endeavor, the alpha-sulfonamidophosphonate moiety has been identified as new anti-Mtb chemotype through the scaffold hopping as the design strategy, development of an effective synthetic methodology using green chemistry tools, and evaluation of anti-TB activity of the synthesized compounds against Mtb (Mycobacterium tuberculosis) H37Rv. Out of the sixteen compounds, five have been found to have MIC values of 1.56 mu g/mL and one 3.125 mu g/mL. The five most active compounds are non-cytotoxic to RAW 264.7 (mouse leukemic monocyte macrophage) cell lines. The compounds are found to possess acceptable values of the various parameters for drug likeness in accordance with the Lipinski rule with the topological surface area (tPSA) of > 70 that suggest eligibility of these new molecular entities for further consideration as potential drug candidates.
• Hydrophosphonylation of Aldimines under Catalysts‐Free Conditions
  作者：Zhihua Cai、Yecheng Fan、Guangfen Du、Lin He

  DOI：10.1002/cjoc.201200119

  日期：2012.7

  Trimethylsilyl phosphite reacted with aldimines efficiently under catalysts‐free conditions, giving α‐aminophosphonates in good to excellent yields. Furthermore, the reaction can be scaled‐up easily and the high yield can be maintained.

  亚磷酸三甲基甲硅烷基酯与醛亚胺在无催化剂的条件下有效地反应，得到高产的α-氨基膦酸酯。此外，可以轻松扩大反应规模，并保持高收率。