13-acetyl-9-methyl-4-bromo-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.0^2,7]trideca-2,4,6-triene | 1240487-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 13-acetyl-9-methyl-4-bromo-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.0^2,7]trideca-2,4,6-triene
• 英文别名: 1-(4-Bromo-9-methyl-11-thioxo-8-oxa-10,12-diazatricyclo[7,3,1,0 2,7]trideca-2,4,6-trien-13-yl)ethanone；1-(4-bromo-9-methyl-11-sulfanylidene-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-13-yl)ethanone
• CAS: 1240487-13-1
• 化学式: C₁₃H₁₃BrN₂O₂S
• 分子量: 341.228
• InChiKey: RWCSERREQPVYKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫脲 、 乙酰丙酮 、 5-溴水杨醛 以 乙醇 为溶剂， 反应 2.5h， 以91%的产率得到13-acetyl-9-methyl-4-bromo-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.0^2,7]trideca-2,4,6-triene
  参考文献：
  名称：

  Fruit Extract of Averrhoa bilimbi: A Green Neoteric Micellar Medium for Isoxazole and Biginelli-Like Synthesis

  摘要：

  一种无过渡金属/配体/添加剂/促进剂的3-甲基-4-芳基亚甲基异噁唑-5(4H)-酮的合成以及类似Biginelli合成在Averrhoa bilimbi提取物（ABE）的天然酸性介质中进行，采用更清洁和更简便的方法。异噁唑-5(4H)-酮和11-乙酰基-2-甲基-5,6-二氢-2H-2,6-亚甲基苯并[g][1,3,5]-噁二唑嗪-4(3H)-酮分别在室温和乙醇回流温度下在有氧条件下合成。该生态友好、经济廉价、无毒的酸性催化介质来源于可再生资源，其动态相通过光学显微镜、动态光散射（DLS）技术和临界胶束浓度（c.m.c.）测量得到确认。显著的优点包括所获得产品的优异产率、底物处理的多样性、催化剂的重复使用、不使用有害有机溶剂以及废物或副产品的最小化。因此，报道的程序简单、环保，并且是现有异噁唑-5(4H)-酮合成和类似Biginelli合成的可靠替代方案。

  DOI：

  10.1007/s11164-021-04539-y

文献信息

• One-Pot Synthesis of 13-Acetyl-9-methyl-11-oxo(or thioxo)-8-oxa-10,12-diazatricyclo[7.3.1.0^2,7]trideca-2,4,6-trienes under Microwave Irradiation
  作者：Qingfang Cheng、Qifa Wang、Tin Tan、Na Chen、Mei Shuai

  DOI：10.1002/jhet.978

  日期：2012.11

  Oxygen‐bridged monastrol analogs, 13‐acetyl‐9‐methyl‐11‐oxo(or thioxo)‐8‐oxa‐10,12‐diazatricyclo[7.3. 1.02,7]trideca‐2,4,6‐trienes, were synthesized by one‐pot three component condensation reaction of substituted salicylaldehyde, acetylacetone and urea or thiourea with nontoxic, inexpensive, and easily available NaHSO4 as catalyst under microwave irradiation and solvent‐free conditions in short time with good

  氧桥蒙纳斯特类似物13-乙酰基-9-甲基-11-氧代（或thioxo）-8-氧代-10,12-二氮杂三环[7.3。1.0 2,7 ] trideca-2,4,6-三烯是通过取代的水杨醛，乙酰丙酮和尿素或硫脲的一锅三组分缩合反应与无毒，廉价且易于获得的NaHSO 4作为催化剂在微波辐射下合成的。短时间内无溶剂，收率高。产物的结构通过IR，1 H NMR，13 C NMR光谱和元素分析来表征。
• Fruit Extract of Averrhoa bilimbi: A Green Neoteric Micellar Medium for Isoxazole and Biginelli-Like Synthesis
  作者：Bhagyashree M. Patil、Sachinkumar K. Shinde、Ashutosh A. Jagdale、Swati D. Jadhav、Suresh S. Patil

  DOI：10.1007/s11164-021-04539-y

  日期：2021.10

  A transition metal/ligand/additive/promoter-free synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones and the Biginelli-like synthesis is carried out in a natural acidic medium of Averrhoa bilimbi extract (ABE) with cleaner and facile approach smentioned here. The isoxazol-5(4H)-ones and 11-acetyl-2-methyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]-oxadiaazocin-4(3H)-ones are synthesized, respectively, under aerobic conditions at room temperature and at reflux temperature of ethanol. This eco-friendly and economically cheap, non-toxic acidic catalytic media is obtained from the renewable resource, and its dynamic phase is confirmed by the optical microscopy, DLS technique, and with critical micelle concentration (c.m.c.) measurements. The notable advantages are excellent yields of the obtained products, versatility in handling substrates, reuse of the catalyst, use of no hazardous organic solvents, and minimization of waste or side products. So, the reported procedure is simple, evergreen, and a sound alternative to the existing protocols for isoxazol-5(4H)-one synthesis and for Biginelli-like synthesis as well.

  一种无过渡金属/配体/添加剂/促进剂的3-甲基-4-芳基亚甲基异噁唑-5(4H)-酮的合成以及类似Biginelli合成在Averrhoa bilimbi提取物（ABE）的天然酸性介质中进行，采用更清洁和更简便的方法。异噁唑-5(4H)-酮和11-乙酰基-2-甲基-5,6-二氢-2H-2,6-亚甲基苯并[g][1,3,5]-噁二唑嗪-4(3H)-酮分别在室温和乙醇回流温度下在有氧条件下合成。该生态友好、经济廉价、无毒的酸性催化介质来源于可再生资源，其动态相通过光学显微镜、动态光散射（DLS）技术和临界胶束浓度（c.m.c.）测量得到确认。显著的优点包括所获得产品的优异产率、底物处理的多样性、催化剂的重复使用、不使用有害有机溶剂以及废物或副产品的最小化。因此，报道的程序简单、环保，并且是现有异噁唑-5(4H)-酮合成和类似Biginelli合成的可靠替代方案。