3-(benzothiazol-2-ylamino)-1-phenylpropan-1-one | 7269-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzothiazol-2-ylamino)-1-phenylpropan-1-one
• 英文别名: 3-benzothiazol-2-ylamino-1-phenyl-propan-1-one；2-<3-Phenyl-3-oxo-propylamino>-benzothiazol
• CAS: 7269-68-3
• 化学式: C₁₆H₁₄N₂OS
• 分子量: 282.366
• InChiKey: WBNMLVBNQJFYOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(benzothiazol-2-ylamino)-1-phenylpropan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以72%的产率得到3-(benzothiazol-2-ylamino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  Synthesis and Anticonvulsant Activity of 3-(6-Substituted-benzothiazol-2-yl)-6-phenyl-[1, 3]-xazinane-2-thiones

  摘要：

  A new series of 3-(6-substituted-benzothiazol-2-yl)-6-phenyl-[1,3]-oxazinane-2-thiones (4 a-j) has been synthesised using an appropriate synthetic route (Scheme 1) and characterised by elemental analyses and spectral (IR, H-1 NMR, C-13 NMR, and El MS) data. The anticonvulsant activity of all the title compounds (4 a-j) was evaluated against Maximal Electroshock (MES) induced seizures and furthermore the most potent compounds were evaluated against subcutaneous pentylene-in mice. The neurotoxicity was assessed tetrazole (sc PTZ) induced seizures model, using the rotorod procedure. All the test compounds were administered intraperitoneally at various dose levels ranging from 30-200 mg/kg body wt and the median effective dose (ED50), median toxic dose (TD50), and protection index (PI) values were determined (Table 2). Among the compounds tested, the 3-(6-dimethylaminobenzothiazol-2-yl)-6-phenyl-[1,3]-oxazinane-2-thiones (4j) was found to be the most potent (ED50: 9.85 and 14.8 in MES model and 12 and 17 in scPTZ model at t = 0.5 h and 4 h, respectively, and TD50 42.8 and 44 at t = 0.5 h and 4 h, respectively, which has been found to be significant at p < 0.01 with respect to reference standard phenytoin) with protection index (PI) 4.85.

  DOI：

  10.1002/1521-4184(200211)335:8<381::aid-ardp381>3.0.co;2-s
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 、 2-氨基苯并噻唑 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 甲苯 为溶剂， 以88 %的产率得到3-(benzothiazol-2-ylamino)-1-phenylpropan-1-one
  参考文献：
  名称：

  银 (I) 催化和 DBU 促进的炔丙醇与胺的异构化/加成反应得到 β-氨基酮

  摘要：

  另一种合成 β-氨基酮的策略是通过银 (I) 催化和 DBU 促进的炔丙醇与胺的异构化/加成实现的。该机制可能涉及异构化和顺序加成与烯基自由基过程相结合。该方案具有底物范围广、原子经济性优越、操作简单、收率优良等特点，为克级药物的合成提供了一种新方法，为β-氨基酮的构建提供了实际应用。

  DOI：

  10.1016/j.tetlet.2024.155163

文献信息

• I₂-catalyzed intramolecular oxidative amination of C(sp³)–H bond: efficient access to 3-acylimidazo[1,2-<i>a</i>]pyridines under neat condition
  作者：Lilan Huang、Wenqing Yin、Jian Wang、Chunfang Gan、Yanmin Huang、Chusheng Huang、Yimiao He

  DOI：10.1039/c8ra10118c

  日期：——

  An efficient and “green” protocol for the synthesis of 3-acylimidazo[1,2-a]pyridines through intramolecular oxidative α-amination of carbonyl compounds has been developed. The reaction proceeds smoothly utilizing I2 as a catalyst and H2O2 as an oxidant under neat condition with broad substrate scope. Several complex nitrogen-containing fused rings are conveniently constructed, which are not easy to

  已经开发了一种通过羰基化合物的分子内氧化 α-胺化合成 3-酰基咪唑并[1,2- a ]吡啶的有效且“绿色”的方案。以I 2为催化剂，H 2 O 2为氧化剂，反应在纯净条件下顺利进行，底物范围广。几个复杂的含氮稠环结构方便，传统方法不易获得。
• ALKYLATION OF CYCLIC AMIDINES WITH MANNICH BASES
  作者：C. Podesva、K. Vagi

  DOI：10.1139/v66-282

  日期：1966.8.1

  not available

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