(Z)-2-benzylidene-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one | 161530-37-6

• 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)-2-benzylidene-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one
• 英文别名: 2-benzylidene-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one；(Z)-2-benzylidene-4-methyl-2H-1,4-benzoxazin-3(4H)-one；(2Z)-2-benzylidene-4-methyl-1,4-benzoxazin-3-one
• CAS: 161530-37-6
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: OAEQXULZLCEHJE-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基-C-苯基硝酮 、 (Z)-2-benzylidene-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 以 甲苯 为溶剂， 反应 96.0h， 以16%的产率得到(3R,4S,5S)-2,4'-dimethyl-3,4-diphenylspiro[1,2-oxazolidine-5,2'-1,4-benzoxazine]-3'-one
  参考文献：
  名称：

  Croce, Piero Dalla; Ferraccioli, Raffaella; Rosa, Concetta La, Heterocycles, 1995, vol. 40, # 1, p. 349 - 356

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯酚 在 sodium methylate 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 32.5h， 生成 (Z)-2-benzylidene-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-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

• Palladium-Catalyzed One-Pot Approach to 3-(Diarylmethylene)oxindoles from Propiolamidoaryl Triflate
  作者：Dahye Lee、Sunhwa Park、Yoseb Yu、Kye Shin、Jae Seo

  DOI：10.3390/molecules200814022

  日期：——

  3-(Diarylmethylene)oxindoles have been synthesized from propiolamidoaryl triflate utilizing a palladium-catalyzed one-pot reaction consisting of three successive reactions: Sonogashira, Heck, and Suzuki-Miyaura. This method allows for the production of a complex skeleton of 3-(diarylmethylene)oxindole from propiolamidoaryl triflate using a commercially available aryl iodide and arylboronic acid in a simple and efficient way with moderate yield and stereoselectivity.

  通过丙炔酰胺基芳基三氟甲磺酸盐的钯催化一步反应，包括三个连续反应：Sonogashira反应、Heck反应和Suzuki-Miyaura反应，合成得到了3-(二芳甲叉基)吲哚。该方法使得从商业上可获得的芳基碘和芳基硼酸出发，通过简单高效的方式，以中等产率和立体选择性，从丙炔酰胺基芳基三氟甲磺酸盐合成得到3-(二芳甲叉基)吲哚的复杂骨架。
• One-Pot Synthetic Approaches for the Construction of Isochroman-4-ones and Benzoxazin-3-ones Using O,P-Acetals
  作者：Tomohiro Maegawa、Akira Nakamura、Kouhei Yamamoto、Ryo Murakami、Norihito Kawashita、Kouichi Matsumoto

  DOI：10.1055/a-1523-1597

  日期：2021.10

  A method for synthesizing six-membered heterocyclic compounds was developed based on the features of O,P-acetals. Sequential reactions of intramolecular cyclization between the methylene carbon atom of O,P-acetal and its electrophilic functional group (ester or protected carbamate) was followed by Horner–Wadsworth–Emmons (HWE) olefination with various aldehydes. The developed one-pot method yielded

  基于O,P-缩醛的特点，开发了一种六元杂环化合物的合成方法。O,P-缩醛的亚甲基碳原子与其亲电子官能团（酯或受保护的氨基甲酸酯）之间发生分子内环化的顺序反应，然后是霍纳-沃兹沃思-埃蒙斯（HWE）与各种醛的烯化反应。开发的一锅法产生了带有亚烷基部分的 isochroman-4-one 和 benzoxazin-3-one 衍生物。
• Biomimetic design of an α-ketoacylphosphonium-based light-activated oxygenation auxiliary
  作者：Ryoto Oya、Kenji Ota、Masaaki Fuki、Yasuhiro Kobori、Masahiro Higashi、Kazunori Nagao、Hirohisa Ohmiya

  DOI：10.1039/d3sc03572g

  日期：——

  The biomimetic design of a transition metal complex based on the iron(IV)-oxo porphyrin π-cation radical species in cytochrome P450 enzymes has been studied extensively. Herein, we translate the functions of this iron(IV)-oxo porphyrin π-cation radical species to an α-ketoacyl phosphonium species comprised of non-metal atoms and utilize it as a light-activated oxygenation auxiliary for ortho-selective

  基于细胞色素 P450 酶中铁（IV）-氧代卟啉 π-阳离子自由基物种的过渡金属配合物的仿生设计已得到广泛研究。在此，我们将这种铁( IV )-氧代卟啉π-阳离子自由基物种的功能转化为由非金属原子组成的α-酮酰基鏻物种，并将其用作苯胺邻位选择性氧化的光激活氧化辅助剂。可见光照射将 α-酮酰基鏻物质转化为激发态，充当瞬时产生的氧化剂。该过程的分子内性质确保了高区域选择性和化学选择性。辅助装置可轻松拆卸。还描述了一锅法。
• Croce Piero Dalla, Ferraccioli Raffaella, Rosa Concetta La, Heterocycles, 40 (1995) N 1, S 349-355
  作者：Croce Piero Dalla, Ferraccioli Raffaella, Rosa Concetta La

  DOI：——

  日期：——
• BARTSCH, H.;NEUBAUER, G.;SADLER, A., SCI. PHARM., 1985, 53, N 2, 111-117
  作者：BARTSCH, H.、NEUBAUER, G.、SADLER, A.

  DOI：——

  日期：——