3-(4-bromophenyl)-7-methyl-2H-1,4-benzoxazine | 1318877-20-1

• 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: 3-(4-bromophenyl)-7-methyl-2H-1,4-benzoxazine
• CAS: 1318877-20-1
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: QTXPVXDMRLYDPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-7-methyl-2H-1,4-benzoxazine 在 bis-triphenylphosphine-palladium(II) chloride 、 二氟化氢钾 、 potassium acetate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Design and synthesis of boron containing 2,4-disubstituted-phthalazin-1(2H)-one and 3,7-disubstituted-2H-benzo[b][1,4] oxazine derivatives as potential HGF-mimetic agents

  摘要：

  We synthesized boron containing 2-(4-methoxybenzyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioaborolan-2-yl)phenyl) phthalazin-1(2H)-one 3 and 7-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[b][1,4] oxazine 8. The reaction of compound 2 with B(2)pin(2) using potassium acetate as the base and Pd(PPh3)(2)Cl-2 as the catalyst, produced the corresponding boron-containing derivative 3 as a white solid in 65% yield. Alternatively, we have synthesized compound 8 as a yellow solid in 59% yield using the Miyaura borylation reaction. The potassium trifluoro(44-methyl-2H-benzo[b][1,4]oxazine-3-yl)phenylborate 9 was then obtained after treatment of 8 with aqueous solution of KF2H in methanol as white solid product in 60% yield. The biological activities of the synthetic compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.032
• 作为产物：
  描述：

  6-氨基间甲酚 、 2,4'-二溴苯乙酮 在 四丁基醋酸铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 3-(4-bromophenyl)-7-methyl-2H-1,4-benzoxazine
  参考文献：
  名称：

  铑催化的[3 + 2]环状芳族醛亚胺/丁酮和N-取代的马来酰亚胺

  摘要：

  这项研究报道了一种新型的铑催化的C–H活化引发[3 + 2]芳族醛亚胺或酮亚胺和马来酰亚胺的环化反应。广泛范围的不带吸电子基团的一般亚胺被成功活化，可以与N-取代的马来酰亚胺有效反应，以良好的收率和优异的非对映选择性提供周环，多手性中心胺。

  DOI：

  10.1021/acs.orglett.8b02671

文献信息

• RETINOIC ACID RECEPTOR ANTAGONISTS AS CHAPERONE-MEDIATED AUTOPHAGY MODULATORS AND USES THEREOF
  申请人：ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY

  公开号：US20150166492A1

  公开（公告）日：2015-06-18

  Compounds, compositions and methods are provided for selectively activating chaperone-mediated autophagy (CMA), protecting cells from oxidative stress, proteotoxicity and lipotoxicity, and/or antagonizing activity of retinoic acid receptor alpha (RARα) in subjects in need thereof.

  本发明提供了一种选择性激活伴随蛋白介导的自噬（CMA），保护细胞免受氧化应激、蛋白毒性和脂毒性的化合物、组合物和方法，并/或在需要的受试者中拮抗视黄酸受体α（RARα）的活性。
• US9512092B2
  申请人：——

  公开号：US9512092B2

  公开（公告）日：2016-12-06
• A Rhodium-Catalyzed [3 + 2] Annulation of General Aromatic Aldimines/Ketimines and <i>N-</i>Substituted Maleimides
  作者：Chengfeng Zhu、Jichao Luan、Jun Fang、Xu Zhao、Xiang Wu、Yougui Li、Yunfei Luo

  DOI：10.1021/acs.orglett.8b02671

  日期：2018.9.21

  A new class of rhodium-catalyzed, C–H activation triggered [3 + 2] annulations of aromatic aldimines or ketimines and maleimides was reported in this study. A broad scope of general imines without electron-withdrawing groups were successfully activated and could effectively react with N-substituted maleimide to afford pericyclic, multichiral centered amines in good yields and with excellent diastereoselectivity

  这项研究报道了一种新型的铑催化的C–H活化引发[3 + 2]芳族醛亚胺或酮亚胺和马来酰亚胺的环化反应。广泛范围的不带吸电子基团的一般亚胺被成功活化，可以与N-取代的马来酰亚胺有效反应，以良好的收率和优异的非对映选择性提供周环，多手性中心胺。
• Design and synthesis of boron containing 2,4-disubstituted-phthalazin-1(2H)-one and 3,7-disubstituted-2H-benzo[b][1,4] oxazine derivatives as potential HGF-mimetic agents
  作者：Bhaskar C. Das、Xiang-Ying Tang、Swarnava Sanyal

  DOI：10.1016/j.tetlet.2011.06.032

  日期：2011.8

  We synthesized boron containing 2-(4-methoxybenzyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioaborolan-2-yl)phenyl) phthalazin-1(2H)-one 3 and 7-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[b][1,4] oxazine 8. The reaction of compound 2 with B(2)pin(2) using potassium acetate as the base and Pd(PPh3)(2)Cl-2 as the catalyst, produced the corresponding boron-containing derivative 3 as a white solid in 65% yield. Alternatively, we have synthesized compound 8 as a yellow solid in 59% yield using the Miyaura borylation reaction. The potassium trifluoro(44-methyl-2H-benzo[b][1,4]oxazine-3-yl)phenylborate 9 was then obtained after treatment of 8 with aqueous solution of KF2H in methanol as white solid product in 60% yield. The biological activities of the synthetic compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.