2,2-diethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one | 77773-92-3

• 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: 2,2-diethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one
• 英文别名: 2,3-Dihydro-2,2-diethyl-4H-1,3-benzoxazin-4-one；2,2-diethyl-2,3-dihydro-benz[e][1,3]oxazin-4-one；2,2-Diaethyl-2,3-dihydro-benz[e][1,3]oxazin-4-on；2,2-diethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one；2,2-diethyl-3H-1,3-benzoxazin-4-one
• CAS: 77773-92-3
• 化学式: C₁₂H₁₅NO₂
• mdl: MFCD18432248
• 分子量: 205.257
• InChiKey: PBFTWQNHRHZVPF-UHFFFAOYSA-N

物化性质

• 熔点：
  99-100 °C(Solv: hexane (110-54-3))
• 沸点：
  388.6±22.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-diethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one 在 三氯氧磷 、 三氯化磷 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 2-[(5-trifluoromethyl)-1H-benzimidazol-2-yl]phenol
  参考文献：
  名称：

  Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases

  摘要：

  A series of 16 substituted 2-(2-hydroxphenyl)benzimidazoles was synthesized and evaluated in vitro for antibacterial activity against bacteria associated with periodontal diseases. Several compounds demonstrated a high level of activity, in tube dilution assay, against Actinomycetes viscosus and Bacteriodes gingivalis. These results indicate that several of these compounds may serve as topical antibacterial agents for the control of acute marginal inflammatory gingivitis and periodontitis.

  DOI：

  10.1021/jm00384a035
• 作为产物：
  描述：

  3-戊酮 、 水杨酰胺 在 氯仿 、 硫酸 作用下， 生成 2,2-diethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one
  参考文献：
  名称：

  The Condensation of Salicylamide with Aldehydes and Ketones

  摘要：

  DOI：

  10.1021/ja01158a019

文献信息

• ZnCl₂-promoted domino reaction of 2-hydroxybenzonitriles with ketones for synthesis of 1,3-benzoxazin-4-ones
  作者：Ziqi Su、Hongxin Chai、Juan Xu、Jiarong Li

  DOI：10.1039/d1ra04194k

  日期：——

  A ZnCl2-promoted synthesis of 1,3-benzoxazin-4-one from 2-hydroxybenzonitriles and ketones was developed. This method displays facile access to a diverse range of substituted 1,3-benzoxazin-4-ones in good yields. This synthetic protocol has advantages: (i) easy availability of starting material; (ii) strong corrosive acid-free condition; (iii) high yield.

  开发了一种ZnCl 2促进的由2-羟基苯甲腈和酮合成1,3-苯并恶嗪-4-酮的方法。该方法能够以良好的产率轻松获得各种取代的 1,3-苯并恶嗪-4-酮。该合成方案具有以下优点：（i）起始材料易于获得；(ii) 强腐蚀无酸条件；(三)高产。
• Highly stereoselective and practical synthesis of a key intermediate for 1-β-methylcarbapenems
  作者：Takeshi Yamanaka、Masahiko Seki、Tooru Kuroda、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/0040-4039(96)00980-x

  日期：1996.7

  acetoxyazetidinone 3 to give an adduct 4b in 87% yield with virtually complete β-selectivity which was transformed by simple hydrolysis into the optically pure azetidinone-4-isopropionic acid derivative 5, a key intermediate of 1-β-methylcarbapenems.

  使由N-丙酰基-2、2-二乙基-1、3-苯并恶嗪酮2b生成的烯醇钠与乙酰氧基氮杂环丁酮3反应，以87％的收率得到加合物4b，其β-选择性几乎完全，可通过简单水解转化为加合物光学纯的氮杂环丁酮-4-异丙酸衍生物5（1-β-甲基卡巴南的关键中间体）。
• Wachi, Kazuyuki; Terada, Atsusuke, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 2, p. 465 - 472
  作者：Wachi, Kazuyuki、Terada, Atsusuke

  DOI：——

  日期：——
• A new amine catalyzed synthesis of 2-substituted 2,3-dihydro-4H-1,3-benzoxazin-4-ones
  作者：Ronald B. Gammill

  DOI：10.1021/jo00329a041

  日期：1981.7
• A novel synthesis of a key intermediate for penems and carbapenems utilizing lipase-catalyzed kinetic resolution
  作者：Masahiko Seki、Toshiyuki Furutani、Tsutomu Miyake、Takeshi Yamanaka、Hiroshi Ohmizu

  DOI：10.1016/0957-4166(96)00132-2

  日期：1996.5

  Titanium enolate-mediated aldol reaction of N-phthaloyl-beta-alanyl-1, 3-benzoxazinone 5 with acetaldehyde gave the (+/-)-syn-aldol (+/-)-6 in a high yield with high diastereoselectivity. Lipase-catalyzed hydrolysis of the corresponding laurate (+/-)-7b furnished enantiomerically pure (2S, 3R)-N-(2-phthaloylaminomethyl-3-hydroxybutyryl)-1, 3-benzoxazinone 6 in 49% yield. Silylation of the hydroxy group of (29, 3R)-6 follwed by deprotection of the amino and carboxy groups gave the beta-amino acid derivative 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems. Copyright (C) 1996 Elsevier Science Ltd