2(1H)-异喹啉碳杂氧杂脒,3,4-二氢-N-羟基-1,8-二甲基- | 84529-13-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2(1H)-异喹啉碳杂氧杂脒,3,4-二氢-N-羟基-1,8-二甲基-
• 英文名称: 3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
• 英文别名: 2H-1,4-Benzoxazin-2-one, 3,4-dihydro-3-methyl-；3-methyl-3,4-dihydro-1,4-benzoxazin-2-one
• CAS: 84529-13-5
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: QKXXBIFQENFWPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-2H-1,4-苯并恶嗪-2-酮 在 iron(II) triflate 、 菲啶 、 十二羰基三铁 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 65.0 ℃ 、5.0 MPa 条件下， 反应 24.0h， 以85%的产率得到2(1H)-异喹啉碳杂氧杂脒,3,4-二氢-N-羟基-1,8-二甲基-
  参考文献：
  名称：

  铁催化氢化用于NAD（P）H模型的原位再生：仿生还原α-酮基/α-氨基酯

  摘要：

  两根熨斗使表面光滑：NAD（P）H模型易于通过分子氢进行铁催化还原而在原位再生。在存在铁基路易斯酸（LA）的情况下，随后的仿生还原α-酮/α-亚氨基酸酯的过程进展顺利，以良好的产率提供了α-羟基酯和氨基酸酯（参见方案； NAD（P））+＝烟酰胺腺嘌呤二核苷酸（磷酸盐），TM ＝过渡金属）。

  DOI：

  10.1002/anie.201301972

文献信息

• Pd/C-catalyzed Reductive Mono-<i>N</i>-alkylation of Nitrophenol Derivatives in One-pot Way
  作者：Zhonghao Jin、Dao Li、Xingyi Wang、Qin Xiao

  DOI：10.1002/cjoc.201090029

  日期：2010.1

  A range of different nitrophenol derivatives were converted in one‐pot to the corresponding secondary alkyl aminophenols in good to excellent yields by using ketones as alkyl source and hydrogen over 10 wt% Pd/C as reducing agent. In all examples, except for one, the secondary amine was the sole alkylation product isolated. When aldehydes were used as alkyl source, the corresponding tertiary amine

  通过使用酮作为烷基源，使用氢含量超过10 wt％的Pd / C作为还原剂，可以将一系列不同的硝基苯酚衍生物一次转化为相应的仲烷基氨基苯酚，收率良好。在所有实施例中，除了一个以外，仲胺是分离的唯一烷基化产物。当醛用作烷基源时，分离出相应的叔胺作为唯一的烷基化产物。
• Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines
  作者：Yixiao Pan、Changjun Chen、Xin Xu、Haoqiang Zhao、Jiahong Han、Huanrong Li、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1039/c7gc03095a

  日期：——

  B(C₆F₅)₃-Catalyzed tandem cyclization/hydrosilylation for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines from readily available starting materials has been developed.

  B(C6F5)3催化的串联环化/氢硅烷化反应，可从易得的起始物构建1,2,3,4-四氢喹啉。
• The First General, Highly Enantioselective Lewis Base Organo- catalyzed Hydrosilylation of Benzoxazinones and Quinoxalinones
  作者：Zhou-Yang Xue、Yan Jiang、Xiao-Zhi Peng、Wei-Cheng Yuan、Xiao-Mei Zhang

  DOI：10.1002/adsc.201000274

  日期：2010.9.10

  The first general, highly enantioselective hydrosilylation of benzoxazinones and quinoxalinones has been developed. The chiral Lewis base organocatalysts that are readily accessible from (1S,2R)‐ephedrine and (1R,2S)‐ephedrine promoted the title reaction to afford various chiral dihydrobenzoxazinones and dihydroquinoxalinones with good yields as well as good enantioselectivities.

  已经开发出第一个一般的苯并恶嗪酮和喹喔啉酮的高度对映选择性加氢硅烷化反应。易于从（1 S，2 R）-麻黄碱和（1 R，2 S）-麻黄碱获得的手性Lewis碱有机催化剂促进了标题反应，从而提供了具有良好收率和良好对映选择性的各种手性二氢苯并恶嗪酮和二氢喹喔啉。
• Manganese Pentacarbonyl Bromide as Regeneration Catalyst Enabled Biomimetic Asymmetric Reduction
  作者：Zheng Liu、Yan-Jiang Yu、Yu-Qing Bai、Mu-Wang Chen、Yong-Gui Zhou

  DOI：10.1021/acs.orglett.4c00425

  日期：2024.4.5

  Using readily available manganese pentacarbonyl bromide as a regeneration catalyst, biomimetic asymmetric reduction of imines including quinoxalinones, benzoxazinones, and benzoxazine has been successfully developed in the presence of transfer catalyst chiral phosphoric acids, providing the chiral amines with high yields and enantioselectivities.

  使用易于获得的五羰基溴化锰作为再生催化剂，在转移催化剂手性磷酸的存在下成功开发了包括喹喔啉酮、苯并恶嗪酮和苯并恶嗪在内的亚胺的仿生不对称还原，提供了高产率和对映选择性的手性胺。
• Microwave-assisted one-pot regioselective synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines
  作者：Wei-Min Dai、Xuan Wang、Chen Ma

  DOI：10.1016/j.tet.2005.04.072

  日期：2005.7

  A protocol for regioselective one-pot synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been developed. Starting from commercially available 2-aminophenols, a base-mediated regioselective O-alkylation took place with 2-bromoalkanoates to give the acyclic intermediates, which underwent spontaneously an intramolecular amidation reaction to furnish 2-alkyl-3,4-dihydro-3-oxo-2H-1.4-benzoxazines in 44-82% yields. For the acyclic intermediate possessing an electron-withdrawing group, microwave heating was necessary for the annulation reaction. (c) 2005 Elsevier Ltd. All rights reserved.