5-chloro-2,3-dihydro-1-benzoxepin-4-carboxaldehyde | 14063-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 5-chloro-2,3-dihydro-1-benzoxepin-4-carboxaldehyde
• 英文别名: 5-chloro-2,3-dihydrobenzo[b]oxepine-4-carbaldehyde；5-chloro-2,3-dihydro-1-benzoxepine-4-carbaldehyde
• CAS: 14063-84-4
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: SIZZLPNGOVAVEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2,3-dihydro-1-benzoxepin-4-carboxaldehyde 在 palladium diacetate 、 sodium chlorite 、 氯化亚砜 、 四丁基溴化铵 、 双氧水 、 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 生成 7,8-Dihydro-5,9-dioxa-benzo[6,7]cyclohepta[1,2-a]naphthalen-6-one
  参考文献：
  名称：

  A rapid access to coumarin derivatives (using Vilsmeier–Haack and Suzuki cross-coupling reactions)

  摘要：

  A four-step preparation of compounds containing a coumarinic moiety is presented. This synthesis involves notably a Suzuki cross-coupling reaction (performed in aqueous Media) and a ring closure by formation of delta-lactone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02373-5
• 作为产物：
  描述：

  2-(2-乙酰基苯氧基)-1-溴乙烷 在 sodium hydride 、 三氯氧磷 作用下， 生成 5-chloro-2,3-dihydro-1-benzoxepin-4-carboxaldehyde
  参考文献：
  名称：

  Structure-based design of thienobenzoxepin inhibitors of PI3-kinase

  摘要：

  Starting from thienobenzopyran HTS hit 1, co-crystallization, molecular modeling and metabolic analysis were used to design potent and metabolically stable inhibitors of PI3-kinase. Compound 15 demonstrated PI3K pathway suppression in a mouse MCF7 xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.124

文献信息

• BENZOPYRAN AND BENZOXEPIN PI3K INHIBITOR COMPOUNDS AND METHODS OF USE
  申请人：Do Steven

  公开号：US20090247567A1

  公开（公告）日：2009-10-01

  Benzopyran and benzoxepin compounds of Formulas I and II, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formulas I and II for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  Benzopyran和benzoxepin的化合物I和II的分子式，包括其立体异构体、几何异构体、互变异构体、溶剂合物、代谢物和药学上可接受的盐，可用于抑制脂质激酶，包括p110 alpha和PI3K的其他同系物，并用于治疗由脂质激酶介导的癌症等疾病。公开了使用分子式I和II的化合物在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗此类疾病或相关病理条件的方法。
• Palladium-Catalyzed C-C Bond Formation from β-Chloroacroleins in Aqueous Media
  作者：Stéphanie Hesse、Gilbert Kirsch

  DOI：10.1055/s-2001-12775

  日期：——

  The Suzuki coupling of several β-chloroacroleins with arylboronic acids was successfully performed with good yields under mild conditions (3 h at 45 °C) in aqueous media without any organic co-solvent.

  几种β-氯丙烯醛与芳基硼酸的铃木偶联反应在温和条件下（45°C下反应3小时）成功进行，且收率良好，反应在水相中进行，无需任何有机共溶剂。
• Studies on the reactivity of new types of tetracyclic-1,5-benzoxazepines: Part V
  作者：Batchu Chandra Sekhar、Devalla Venkata Ramana、Sukuru Raghu Ramadas

  DOI：10.1002/jhet.5570380211

  日期：2001.3

  The syntheses of tetracyclic 1,5-benzoxazepines 3a-e from heterocyclic (3-chloroaldehydes 1a-e and 2-aminophenol are reported herein (Scheme I). Attempted lithium aluminium hydride (LiAlH4) reduction of the imine double bond in 3a-e failed to furnish the corresponding saturated compounds 5a-e. Attempted catalytic hydrogenation of 3a-e in the presence of acetic acid and acetic anhydride gave surprisingly

  本文报道了由杂环（3-氯醛1a-e和2-氨基苯酚）合成四环1,5-苯并x庚因3a-e（方案I）尝试氢化氢化锂铝（LiAlH 4）还原3a-亚胺双键e未能提供相应的饱和化合物5a-e。在乙酸和乙酸酐的存在下尝试进行3a-e的催化加氢令人惊讶地仅以高收率得到了乙酰氧基衍生物6a-e（方案II）。碱催化的乙酰氧基水解衍生物6a-e如预期提供了相应的酚类衍生物7a-e，产量中等。然而，尝试用巯基乙酸或其甲酯对3a-e进行环官能化以获得新的五环杂环4a-e并不成功。
• Benzopyran and benzoxepin PI3K inhibitor compounds and methods of use
  申请人：Genentech, Inc.

  公开号：US07928248B2

  公开（公告）日：2011-04-19

  Benzopyran and benzoxepin compounds of Formulas I and II, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formulas I and II for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式I和II的苯并吡喃和苯并氧杂环化合物，包括立体异构体、几何异构体、互变异构体、溶剂化物、代谢物和药学上可接受的盐，可用于抑制脂质激酶，包括p110α和其他PI3K同系物，并用于治疗由脂质激酶介导的癌症等疾病。公开了使用公式I和II化合物在哺乳动物细胞中进行体外、体内和原位诊断、预防或治疗此类疾病或相关病理条件的方法。
• 4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene compounds
  申请人：Do Steven

  公开号：US08399690B2

  公开（公告）日：2013-03-19

  Benzopyran and benzoxepin compounds of Formulas I and II, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formulas I and II for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

  公式I和II中的苯并吡喃和苯并氧杂环化合物，包括立体异构体、几何异构体、互变异构体、溶剂化物、代谢物和其药学上可接受的盐，可用于抑制脂质激酶，包括p110α和其他PI3K同系物，并用于治疗由脂质激酶介导的癌症等疾病。本文揭示了使用公式I和II化合物的方法，用于哺乳动物细胞中的体外、体内诊断、预防或治疗此类疾病或相关病理条件。