6-chloro-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one | 82944-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 6-chloro-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
• 英文别名: 6-Chloro-2,2-dimethyl-benzo[1,3]dioxin-4-one；6-chloro-2,2-dimethyl-1,3-benzodioxin-4-one
• CAS: 82944-16-9
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: LPCHPOPJHXAXEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-chloro-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 、 (4aR,8aS)-3-(Octahydro-quinolin-1-yl)-propylamine 以 甲苯 为溶剂， 生成 5-Chloro-2-hydroxy-N-[(4aR,8aS)-3-(octahydro-quinolin-1-yl)-propyl]-benzamide
  参考文献：
  名称：

  Salicylamide inhibitors of influenza virus fusion

  摘要：

  Structural variation of the quinolizidine heterocycle of the influenza fusion inhibitor BMY-27709 was examined by several topological dissections in order to illuminate the critical features of the ring system. This exercise resulted in the identification of a series of synthetically more accessible decahydroquinolines that retained the structural elements of BMY-27709 important for antiviral activity. The 2-methyl-cis-decahydroquinoline 6f was the most potent influenza inhibitor identified that demonstrated an EC50 of 90 ng/mL in a plaque reduction assay. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00335-8
• 作为产物：
  描述：

  5-氯水杨酸乙酯 在 potassium dithionate 、 四乙基溴化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 0.67h， 生成 6-chloro-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  通过醚和硫醚的 α-Csp3-H 活化实现无过渡金属的脱氢环化

  摘要：

  我们在此报道了四乙基溴化铵催化 O- 或 S- 烷基化水杨酸或硫代水杨酸衍生物的分子内氧化环化以获得 4 H -苯并[ d ] [1,3] 二恶英-4-酮或 4 H -苯并[ d ] [ 1,3]oxathiin-4-ones，分别。水杨酸衍生物的氧化环化在 110 °C 通过自由基途径进行。相反，硫代水杨酸的环化在室温下通过离子途径顺利进行。值得注意的是，整体反应速度快，反应时间短，产品收率高，季碳中心形成顺利。

  DOI：

  10.1055/a-2017-6065

文献信息

• An approach to the identification of potent inhibitors of influenza virus fusion using parallel synthesis methodology
  作者：Milind S Deshpande、Jianmei Wei、Guangxiang Luo、Christopher Cianci、Stephanie Danetz、Al Torri、Laurence Tiley、Mark Krystal、Kuo-Long Yu、Stella Huang、Qi Gao、Nicholas A Meanwell

  DOI：10.1016/s0960-894x(01)00459-0

  日期：2001.9

  Structure-activity studies associated with the salicylic acid-derived inhibitor of influenza fusion, BMY-27709, were examined using a parallel synthesis approach. This SAR survey led to the discovery of potent influenza inhibitory activity in a series of aromatic amides and thioamides derived from 1,3,3-trimethyl-5-hydroxycyclohexylmethylamine. Select compounds were characterized as inhibitors of the HI subtype of influenza A viruses that act by preventing the pl-l-induced fusion process, thereby blocking viral entry into host cells. In a plaque-reduction assay, the most potent inhibitors displayed EC50 values of 0.02-0.14 mug/mL. (C) 2001 Elsevier Science Ltd. All rights reserved.