(Z)-3-(2-(4-chlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one | 70372-52-0

• 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-chlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
• 英文别名: 3-[(Z)-2-(4-chloro-phenyl)-2-oxo-ethylidene]-3,4-dihydro-benzo[1,4]oxazin-2-one；(3Z)-3-[2-(4-chlorophenyl)-2-oxoethylidene]-4H-1,4-benzoxazin-2-one
• CAS: 70372-52-0
• 化学式: C₁₆H₁₀ClNO₃
• 分子量: 299.713
• InChiKey: XARBPNLWLGOIKZ-LCYFTJDESA-N

物化性质

• 沸点：
  457.8±45.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 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-chlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one 以89%的产率得到
  参考文献：
  名称：

  Masliwech A. N., Mashewskaja I. W., Krasnykh O. P., Shurow S. N., Andreii+, Zh. organ. khimii, 28 (1992) N 12, S 2545-2553

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯乙酮 在 sodium 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (Z)-3-(2-(4-chlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activity of benzoxazinone derivatives and open-ring analogues: Preliminary data and computational analysis

  摘要：

  This study examines in depth benzoxazine nucleus for antimycobacterial property. We synthesized some benzoxazin-2-one and benzoxazin-3-one derivatives, which were tested for activity against a panel of Mycobacterium tuberculosis (Mtb) strains, including H37Ra, H37Rv and some resistant strains. Several compounds displayed a high antimycobacterial activity and the three isoniazid analogue derivatives 8a-c exhibited a MIC range of 0.125-0.250 mu g/mL (0.37-0.75 mu M) against strain H37Ra, therefore lower than the isoniazid reference drug. Two benzoxazin-2-one derivatives, 1c and 5j, together with isoniazid-analogue compound 8a, also revealed low MIC values against resistant strains and proved highly selective for mycobacterial cells, compared to mammalian Vero cells. To predict whether molecule 8a is able to interact with the active site of InhA, we docked it into the crystal structure; indeed, during the molecular dynamic simulation the compound never left the protein pocket. The more active compounds were predicted for ADME properties and all proved to be potentially orally active in humans.

  DOI：

  10.1016/j.bmcl.2019.07.025

文献信息

• Chemistry of Acyl(imidoyl)ketenes: IX. Synthesis and Thermolysis of 3-Aroyl-8-chloro-1,2-dihydro-4H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones
  作者：T.D. Semenova、O.P. Krasnykh

  DOI：10.1007/s11178-005-0321-9

  日期：2005.8

  Reactions of 3-Z-aroylmethylene-6-chloro-3,4-dihydro-2H-1,4-benzoxazine-2-ones with oxalyl chloride afford 3-aroyl-8-chloro-1,2-dihydro-4H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones and Z-3-(2-aryl-2-chlorovinyl)-6-chloro-2H-1,4-benzoxazine-2-ones. Aroyl(imidoyl)ketenes generated by decarbonylation of pyrrolobenzoxazinetriones undergo dimerization through [4+2]-cycloaddition to form 4-aroyl-3-aroyloxy-2-(2-oxo-2H-1,4-benzoxazin-3-yl)-1H, 5H-pyrido[2,1-c][1,4]benzoxazine-1,5-diones.

  3-Z-芳酰基亚甲基-6-氯-3,4-二氢-2H-1,4-苯并恶嗪-2-酮与草酰氯反应生成 3-芳酰基-8-氯-1,2-二氢-4H-吡咯并[2,1-c][1,4]苯并恶嗪-1,2,4-三酮和 Z-3-(2-芳基-2-氯乙烯基)-6-氯-2H-1,4-苯并恶嗪-2-酮。由吡咯并噁嗪三酮脱羰基生成的丙酰基（酰亚胺酰）酮通过 [4+2] - 环加成反应发生二聚化，形成 4-芳酰基-3-芳酰氧基-2-(2-氧代-2H-1,4-苯并噁嗪-3-基)-1H, 5H-吡啶并[2,1-c][1,4]苯并噁嗪-1,5-二酮。
• Sulfamic Acid as an Effective Catalyst in Solvent‐Free Synthesis of β‐Enaminoketone Derivatives and X‐ray Crystallography of Their Representatives
  作者：Min Xia、Bin Wu、Guo‐Feng Xiang

  DOI：10.1080/00397910701873250

  日期：2008.3.28

  Abstract Two types of β‐enaminoketone derivatives of 3‐(2‐oxo‐2‐arylethylidene)‐3,4‐dihydro‐1H‐quinoxalin‐2‐ones and 3‐(2‐oxo‐2‐arylethylidene)‐3,4‐dihydro‐benzo[1,4]oxazin‐2‐ ones were effectively and conveniently prepared in good to excellent yields under solvent‐free conditions via the catalysis of sulfamic acid in the corresponding condensations of o‐phenylenediamine and o‐aminophenol with ethyl

  摘要 3-(2-oxo-2-arylethylidene)-3,4-dihydro-1H-quinoxalin-2-ones和3-(2-oxo-2-arylethylidene)-3,4的两种β-烯氨基酮衍生物在无溶剂条件下，通过氨基磺酸催化邻苯二胺和邻氨基苯酚与乙基 2 的相应缩合反应，可以有效且方便地制备-二氢苯并[1,4]恶嗪-2-类化合物。 ,4-dioxo-4-arylbutyrate 分别。化合物经 IR、1H NMR 和 13C NMR 确证，代表性化合物通过 X 射线晶体学进一步确定。
• Synthesis, structure and spectral study of two types of novel fluorescent BF2 complexes with heterocyclic 1,3-enaminoketone ligands
  作者：Min Xia、Bin Wu、Guofeng Xiang

  DOI：10.1016/j.jfluchem.2008.01.019

  日期：2008.5

  Two types of novel BF2 complexes are readily obtained by the reaction of BF3OEt with 3-(2-oxo-2-arylethylidene)-3,4-dihydro-1H-quinoxalin-2-ones or 3-(2-oxo-2-arylethylidene)-3,4-dihydrobenzo[1,4]oxazin-2-ones, respectively in refluxing acetic acid/toluene solvent mixture. The complexes are confirmed by elemental analysis, FT-IR, 1H, 13C, 11B, 19F NMR and one of them is executed its X-ray crystallographic

  两种类型的新颖的BF 2个络合物容易由BF的反应获得3 OET与3-（2-氧代-2- arylethylidene）-3,4-二氢-1- ħ -喹喔啉-2-酮或3-（2-氧代-2-芳基亚乙基）-3,4-二氢苯并[1,4]恶嗪-2-酮分别在回流的乙酸/甲苯溶剂混合物中。通过元素分析，FT-IR，1 H，13 C，11 B，19 F NMR证实了该配合物，并对其中之一进行了X射线晶体学研究。这些配合物的出色的光物理性质由紫外可见吸收和荧光发射光谱法确定。
• 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.
• Chemistry of 2-methylene-2,3-dihydro-3-furanones
  作者：E. N. Kozminykh、N. M. Igidov、G. A. Shavkunova、V. O. Kozminykh

  DOI：10.1007/bf02495929

  日期：1997.7

  2-p-Chlorobenzoylmethylene-5-phenyl-2,3-dihydro-3-furanone reacts with arylamines or N-arylideneamines to form the products of ring opening, 1,6-diaryl-1-arylamino-4-hydroxy-1,4-hexadiene-3,6-diones. The reaction of 5-aryl-2-p-chlorobenzoylmethylene-2,3-dihydro-3-furanones with o-aminophenol afforded 3-p-chlorobenzoylmethylene-3,4-dihydro-2H-benzo[b]-1,4-oxazin-2-one. Nucleophilic attack of amines is directed either to electrophilic centers at the C(5) and C(2) atoms or to the carbonyl group of the 2-phenacylidene substituent of the 3-oxofuran ring.