(Z)-3-(2-(4-bromophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one | 70372-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (Z)-3-(2-(4-bromophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
• 英文别名: (3Z)-3-[2-(4-bromophenyl)-2-oxoethylidene]-4H-1,4-benzoxazin-2-one
• CAS: 70372-51-9
• 化学式: C₁₆H₁₀BrNO₃
• 分子量: 344.164
• InChiKey: FTIXRAOPJQQYIK-LCYFTJDESA-N

物化性质

• 沸点：
  472.2±45.0 °C(Predicted)
• 密度：
  1.618±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-(2-(4-bromophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one 、 草酰氯 以 苯 为溶剂， 反应 1.83h， 生成 3-p-bromobenzoyl-2,4-dihydro-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-trione
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: XCVIII. [4 + 2]-cycloaddition of alkyl vinyl ethers to 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones. A new synthetic approach to heteroanalogs of 13(14→8)-abeo steroids

  摘要：

  3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with alkyl vinyl ethers according to the [4 + 2]-cycloaddition pattern with formation of substituted (1S*,16R*)- and (1R*,16R*)-16-alkoxy-14-aryl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-triones. The structure of (1S*,16R*)-7-chloro-16-ethoxy-14-phenyl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-trione was determined by X-ray analysis. A new synthetic approach was developed to heteroanalogs of 13(14 -> 8)-abeo steroids, substituted 3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadecanes.

  DOI：

  10.1134/s1070428013120105
• 作为产物：
  描述：

  3-[6-(4-bromophenyl)-3-cyclohexyl-2-cyclohexylimino-4-oxo-3,4-dihydro-2H-1,3-oxazin-5-yl]-2H-1,4-benzoxazin-2-one 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 (Z)-3-(2-(4-bromophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
  参考文献：
  名称：

  Five-membered 2,3-dioxo heterocycles: LXXXVIII. Reaction of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones with N,N′-dicyclohexylcarbodiimide under thermolysis conditions

  摘要：

  Thermolysis of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones generates aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes which react as dienes at the aroylketene fragment in [4 + 2]-cycloaddition at the C=N bond of N,N'-dicyclohexylcarbodiimide with formation of 3-[6-aryl-4-oxo-3-cyclohexyl-2-cyclohexylimino-3,4-dihydro-2H-1,3-oxazin-5-yl]-2H-1,4-benzoxazin-2-ones. Thermolysis of the latter is accompanied by elimination of N,N'-dicyclohexylcarbodiimide, and aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes thus generated undergo cyclodimerization to produce 7-aroyl-6,10-dioxo-9-(2-oxo-2H-1,4-benzoxazin-3-yl)-6,10-dihydrobenzo[b]pyrido[1,2-d][1,4]oxazin-8-yl benzoates.

  DOI：

  10.1134/s1070428012090151

文献信息

• “On water” ultrasound-assisted one pot efficient synthesis of functionalized 2-oxo-benzo[1,4]oxazines: First application to the synthesis of anticancer indole alkaloid, Cephalandole A
  作者：Pradeep K. Jaiswal、Vashundhra Sharma、Jaroslav Prikhodko、Irina V. Mashevskaya、Sandeep Chaudhary

  DOI：10.1016/j.tetlet.2017.03.048

  日期：2017.5

  For the first time, an efficient, simple, synthetic green protocol for the one-pot synthesis of functionalized 2-oxo-benzo[1,4]oxazines 24–29 in water under ultrasound irradiation is presented. As compared to conventional methods, the present protocol avoids traditional chromatography and purification steps and furnished the target molecules in excellent yields (upto 98%) with no side products. The

  对于第一次，一个高效，简便的，合成的绿协议的一锅合成官能-2-氧代苯并[1,4]恶嗪24 - 29在超声照射下的水被呈现。与常规方法相比，本方案避免了传统的色谱和纯化步骤，并以极高的收率（高达98％）提供了目标分子，且没有副产物。该方法也已在克级合成中得到证明。此外，官能化2-氧代-喹喔啉类似物31 - 33，另一类生物活性杂环支架的，使用这种方法，还制备。该方案首次成功地用于抗癌吲哚生物碱Cephalandole A的合成35。
• Microwave-assisted One-pot Efficient Synthesis of Functionalized 2-Oxo-2-phenylethylidenes-linked 2-Oxobenzo[1,4]oxazines and 2-Oxoquino[1,4]oxalines: Synthetic Applications, Antioxidant Activity, SAR and Cytotoxic Studies
  作者：Vashundhra Sharma、Pradeep K. Jaiswal、Dharmendra K. Yadav、Mukesh Saran、Jaroslav Prikhodko、Manas Mathur、Ajit K. Swami、Irina V. Mashevskaya、Sandeep Chaudhary

  DOI：10.17344/acsi.2017.3709

  日期：2017.12.15

  A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2- phenylethylidene)-3, 4-dihydro-2H-benzo[b][1,4] oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3,4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 +/- 0.08 mu g/mL, 9.89 +/- 0.15 mu g/mL and 8.97 +/- 0.13 mu g/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 mu g/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C-0.5 FRAP = 546.2 mu M). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T(3) fibroblast cell lines using MTT assay.
• Iwanami,Y.; Inagaki,T., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 681 - 684
  作者：Iwanami,Y.、Inagaki,T.

  DOI：——

  日期：——
• Five-membered 2,3-dioxo heterocycles: XCVIII. [4 + 2]-cycloaddition of alkyl vinyl ethers to 3-aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones. A new synthetic approach to heteroanalogs of 13(14→8)-abeo steroids
  作者：E. E. Stepanova、Z. G. Aliev、A. N. Maslivets

  DOI：10.1134/s1070428013120105

  日期：2013.12

  3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with alkyl vinyl ethers according to the [4 + 2]-cycloaddition pattern with formation of substituted (1S*,16R*)- and (1R*,16R*)-16-alkoxy-14-aryl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-triones. The structure of (1S*,16R*)-7-chloro-16-ethoxy-14-phenyl-3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadeca-4,6,8,13-tetraene-2,11,12-trione was determined by X-ray analysis. A new synthetic approach was developed to heteroanalogs of 13(14 -> 8)-abeo steroids, substituted 3,15-dioxa-10-azatetracyclo[8.7.0.0(1,13).0(4,9)]heptadecanes.
• Five-membered 2,3-dioxo heterocycles: LXXXVIII. Reaction of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones with N,N′-dicyclohexylcarbodiimide under thermolysis conditions
  作者：V. A. Maslivets、A. N. Maslivets

  DOI：10.1134/s1070428012090151

  日期：2012.9

  Thermolysis of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones generates aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes which react as dienes at the aroylketene fragment in [4 + 2]-cycloaddition at the C=N bond of N,N'-dicyclohexylcarbodiimide with formation of 3-[6-aryl-4-oxo-3-cyclohexyl-2-cyclohexylimino-3,4-dihydro-2H-1,3-oxazin-5-yl]-2H-1,4-benzoxazin-2-ones. Thermolysis of the latter is accompanied by elimination of N,N'-dicyclohexylcarbodiimide, and aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes thus generated undergo cyclodimerization to produce 7-aroyl-6,10-dioxo-9-(2-oxo-2H-1,4-benzoxazin-3-yl)-6,10-dihydrobenzo[b]pyrido[1,2-d][1,4]oxazin-8-yl benzoates.