4-(allyloxy)-3-[(allyloxy)methyl]benzaldehyde | 189683-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(allyloxy)-3-[(allyloxy)methyl]benzaldehyde
• 英文别名: 4-prop-2-enoxy-3-(prop-2-enoxymethyl)benzaldehyde
• CAS: 189683-83-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: FSPRAQDCXWGDOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-5-甲基-3-硝基苯乙酮 、 4-(allyloxy)-3-[(allyloxy)methyl]benzaldehyde 以to give 470 mg (Yield 45%) of the title compound的产率得到(E)-3-{4-(allyloxy)-3-[(allyloxy)methyl]phenyl}-1-(2-hydroxy-5-methyl-3-nitrophenyl)-2-propen-1-one
  参考文献：
  名称：

  CDK inhibitors having 3-hydroxychromen-4-one structure

  摘要：

  本发明揭示了一种新型的3-羟基香豆素衍生物，其药学上可接受的盐、水合物、溶剂合物或异构体，可用作细胞周期素依赖性激酶（“CDK”）的抑制剂。此外，本发明还揭示了一种制备该化合物的方法和一种组合物，该组合物作为活性成分与药学上可接受的载体一起用于抑制或治疗癌症和由细胞增殖引起的疾病，如炎症、血管狭窄、血管生成等。

  公开号：

  US06683095B2
• 作为产物：
  描述：

  5-溴-2-羟基苯甲醇 在 sodium hydride 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 41.5h， 生成 4-(allyloxy)-3-[(allyloxy)methyl]benzaldehyde
  参考文献：
  名称：

  Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins¹

  摘要：

  Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9.HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of(R)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (R)-7b and c to (R)-salbutamol was not yet possible without racemization.

  DOI：

  10.1021/jo970032d

文献信息

• Cdk inhibitors having 3-hydroxychromen-4-one structure
  申请人：——

  公开号：US20030125356A1

  公开（公告）日：2003-07-03

  The present invention relates to a novel 3-hydroxychromen-4-one derivative of formula (1), pharmaceutically acceptable salt, hydrate, solvate or isomer thereof which is useful as an inhibitor for Cyclin Dependent Kinase (“CDK”); to a process for preparing the compound of formula (1); and to a composition for suppression or treatment of cancer and diseases induced by cell proliferation such as inflammation, angiostenosis, angiogenesis, etc. comprising the compound of formula (1) as an active component together with pharmaceutically acceptable carriers.

  本发明涉及一种新型的3-羟基香豆素-4-酮衍生物，其化学式为(1)，以及其在药理学上可接受的盐、水合物、溶剂合物或同分异构体，该衍生物可用作 Cyclin Dependent Kinase (“CDK”) 的抑制剂；还涉及制备化合物(1)的方法；以及一种用于抑制或治疗癌症和由细胞增殖引起的疾病，如炎症、血管狭窄、血管生成等的组合物，该组合物以化合物(1)作为活性成分，与药理学上可接受的载体一起使用。
• US6683095B2
  申请人：——

  公开号：US6683095B2

  公开（公告）日：2004-01-27
• Synthesis of the Adrenergic Bronchodilators (<i>R</i>)-Terbutaline and (<i>R</i>)-Salbutamol from (<i>R</i>)-Cyanohydrins¹
  作者：Franz Effenberger、Jürgen Jäger

  DOI：10.1021/jo970032d

  日期：1997.6.13

  Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9.HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of(R)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (R)-7b and c to (R)-salbutamol was not yet possible without racemization.
• CDK inhibitors having 3-hydroxychromen-4-one structure
  申请人：LG Life Sciences Ltd.

  公开号：US06683095B2

  公开（公告）日：2004-01-27

  A novel 3-hydroxychromen-4-one derivative, pharmaceutically acceptable salt, hydrate, solvate or isomer thereof which is useful as an inhibitor for Cyclin Dependent Kinase (“CDK”) is disclosed. Further, a process for preparing the compound and a composition for suppression or treatment of cancer and diseases induced by cell proliferation such as inflammation, angiostenosis, angiogenesis, etc. is disclosed comprising the compound as an active component together with pharmaceutically acceptable carriers.

  本发明揭示了一种新型的3-羟基香豆素衍生物，其药学上可接受的盐、水合物、溶剂合物或异构体，可用作细胞周期素依赖性激酶（“CDK”）的抑制剂。此外，本发明还揭示了一种制备该化合物的方法和一种组合物，该组合物作为活性成分与药学上可接受的载体一起用于抑制或治疗癌症和由细胞增殖引起的疾病，如炎症、血管狭窄、血管生成等。