2-(4-ethoxyphenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine | 303121-20-2

• 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: 2-(4-ethoxyphenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
• 英文别名: 2-(4-Ethoxyphenyl)-1H,2H,3H-naphtho[1,2-E][1,3]oxazine；2-(4-ethoxyphenyl)-1,3-dihydrobenzo[f][1,3]benzoxazine
• CAS: 303121-20-2
• 化学式: C₂₀H₁₉NO₂
• mdl: MFCD01916524
• 分子量: 305.376
• InChiKey: BUGRBLIRHCZREP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-乙氧基苯基氨基)乙酸乙酯 、 2-萘酚 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 lipase B Candida antarctica 作用下， 以 水 、 乙腈 为溶剂， 以50%的产率得到2-(4-ethoxyphenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
  参考文献：
  名称：

  酶和光氧化还原顺序催化一锅合成1,3-恶嗪衍生物

  摘要：

  首次介绍了一种将可见光和酶催化结合在一个罐中的新策略，该策略用于从[小的α]-或[小的β]-萘酚和N-芳基甘氨酸乙酯合成1，3-恶嗪衍生物。

  DOI：

  10.1039/c6cy02682f

文献信息

• An Efficient One-Pot Strategies for the Synthesis of [1,3] Oxazine Derivatives
  作者：Sapkal, Suryakant B.、Shelke, Kiran F.、Shingate, Bapurao B.、Shingare, Murlidhar S.

  DOI：10.5012/jkcs.2010.54.4.437

  日期：2010.8.20

  수용액 속에서 $NaHSO_4$, TBAB (phase transfer catalyst), ionic liquid (IL) (1-butyl-3-methyl imidazolium hydrogen sulphate [bmim]$HSO_4$)를 사용하여, formalin, $\beta}$-naphthol, aromatic amines을 반응시켜서 대응하는 2,3-dihydro-2-phenyl-1Hnaphtho-[1,2-e] [1,3] oxazine 유도체를 합성할 수 있는 보다 친환경적이고, 수율이 좋고, 크로마토그래피 분리 방법을 사용하지 않는 합성 방법을 개발하였다. Sodium hydrogen sulphate ($NaHSO_4$), n-tetra butyl ammonium bromide (TBAB) as a phase transfer catalyst (PTC) in water, and 1-butyl-3-methyl imidazolium hydrogen sulphate [bmim]$HSO_4$ as ionic liquid (IL) has been used as a mild reaction promoter for the cyclocondensation of formalin, $\beta}$-naphthol and aromatic amines to afford respective 2,3-dihydro-2-phenyl-1H-naphtho-[1,2-e] [1,3] oxazine derivatives. The present protocols are greener, high yielding and involved the nonchromatographic isolation procedure.

  수용액속에서$NaHSO_4$，TBAB（相转移催化剂）、离子液体（1-丁基-3-甲基咪唑硫酸氢[bmim]$HSO_4$）、福尔马林、$\beta}$-萘酚、2,3- 二氢-2-苯基-1Hnaphtho-[1,2-e] [1,3] oxazine 유도체를 합성할 수 있는 보다 친환경적이고, 수율이 좋고, 크로마토그래피 분리 방법을 사용하지 않는 합성 방법을 개발하였다. 硫酸氢钠（$NaHSO_4$）、作为水中相转移催化剂（PTC）的正丁基溴化铵（TBAB）和作为离子液体（IL）的 1-丁基-3-甲基咪唑硫酸氢盐 [bmim]$HSO_4$ 被用作福尔马林环缩合的温和反应促进剂、$\beta}$-萘酚和芳香胺可分别生成 2,3-二氢-2-苯基-1H-萘并[1,2-e] [1,3] 恶嗪衍生物。本方案更环保、产率高，并采用了非色谱分离程序。
• Polyethylene glycol (PEG) mediated expeditious synthetic route to 1,3-oxazine derivatives
  作者：Pravin V. Shinde、Amol H. Kategaonkar、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.cclet.2011.01.011

  日期：2011.8

  Various 1,3-oxazine derivatives were synthesized in high yields, within shorter reaction times using PEG-400 as a safer medium/mediator. This synthetic route is exceedingly easy and avoids the use of acid/base catalysts. (C) 2011 Murlidhar S. Shingare. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• REPORTER SYSTEM FOR HIGH THROUGHPUT SCREENING OF COMPOUNDS AND USES THEREOF
  申请人：RATAN Rajiv

  公开号：US20130005666A1

  公开（公告）日：2013-01-03

  The NF-E2-related factor 2 (Nrf2) is a key transcriptional regulator of antioxidant defense and detoxification. To directly monitor stabilization of Nrf2 we fused its Neh2 domain, responsible for the interaction with its nucleocytoplasmic regulator, Keap1, to firefly luciferase (Neh2-luciferase). It is shown herein that Neh2 domain is sufficient for recognition, ubiquitination and proteasomal degradation of Neh2-luciferase fusion protein. The novel Neh2-luc reporter system allows direct monitoring of the adaptive response to redox stress and classification of drugs based on the time-course of reporter activation. The novel reporter was used to screen a library of compounds to identify activators of Nrf2. The most robust and yet non toxic Nrf2 activators found—nordihydroguaiaretic acid, fisetin, and gedunin-induced astrocyte-dependent neuroprotection from oxidative stress via an Nrf2-dependent mechanism.
• US9200046B2
  申请人：——

  公开号：US9200046B2

  公开（公告）日：2015-12-01
• Enzyme and photoredox sequential catalysis for the synthesis of 1,3-oxazine derivatives in one pot
  作者：Guo-Yan Zhang、Yang Xiang、Zhi Guan、Yan-Hong He

  DOI：10.1039/c6cy02682f

  日期：——

  A novel strategy combining visible-light and enzyme catalysis in one pot for the synthesis of 1,3-oxazine derivatives from [small alpha]- or [small beta]-naphthols and ethyl N-aryl glycinates is described for the first...

  首次介绍了一种将可见光和酶催化结合在一个罐中的新策略，该策略用于从[小的α]-或[小的β]-萘酚和N-芳基甘氨酸乙酯合成1，3-恶嗪衍生物。