3,5-bis(allyloxy)benzaldehyde | 189683-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(allyloxy)benzaldehyde
• 英文别名: Benzaldehyde, 3,5-bis(2-propenyloxy)-；3,5-bis(prop-2-enoxy)benzaldehyde
• CAS: 189683-82-7
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: SRQYOPLBSPFYOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  3,5-bis(allyloxy)benzaldehyde 在 扁桃腈裂解酶来源于杏仁 作用下， 以 吡啶 、 二氯甲烷 、 异丙醚 为溶剂， 反应 26.0h， 生成 (R)-2-acetoxy-2-(3,5-bis(allyloxy)phenyl)acetonitrile
  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
• 作为产物：
  描述：

  3,5-diallyloxybenzyl alcohol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,5-bis(allyloxy)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

• Sodium Perborate: A Facile Catalyst for Allylation of Active Centers
  作者：Soora Harinath Jayaprakash、Balam Satheesh Krishna、Sthanikam Siva Prasad、Sarva Santhi Sudha、Cirandur Suresh Reddy

  DOI：10.1080/00397911.2014.963874

  日期：2015.2

  groups has been achieved successfully with the reaction of allyl bromide by using sodium perborate as a new catalyst in aqueous media. The advantage of this method is operationally simple, short reaction time, good yield, and simple workup conditions over the previously reported conventional methods such as amination, oxyalkylation reactions of allyl bromide, and Friedel–Crafts allylation chemistry.

  图形摘要 使用过硼酸钠作为水性介质中的新型催化剂，通过烯丙基溴的反应成功实现了 OH、NH 和 CH 基团的高效且环保的烯丙基化。该方法的优点是操作简单、反应时间短、收率好、后处理条件简单，优于之前报道的传统方法，如胺化、烯丙基溴的烷氧基化反应和 Friedel-Crafts 烯丙基化化学。
• COMPOSITION FOR PHOTODYNAMIC THERAPY COMPRISING A MACROMOLECULAR CAPSULE
  申请人：Kim Kimoon

  公开号：US20120045516A1

  公开（公告）日：2012-02-23

  A composition for photodynamic therapy including a polymer capsule having a diameter of about 10 nm to about 2000 nm synthesized by copolymerization of a flat aromatic compound represented by Formula 1 (see the specification) and an organic compound represented by Formula 2 (see the specification).
• METHOD FOR TREATING A PATIENT VIA PHOTODYNAMIC THERAPY COMPRISING A MACROMOLECULAR CAPSULE
  申请人：POSTECH ACADEMY-INDUSTRY FOUNDATION

  公开号：US20130315989A1

  公开（公告）日：2013-11-28

  A composition for photodynamic therapy including a polymer capsule having a diameter of about 10 nm to about 2000 nm synthesized by copolymerization of a flat aromatic compound represented by Formula 1 (see the specification) and an organic compound represented by Formula 2 (see the specification).
• US6974857B1
  申请人：——

  公开号：US6974857B1

  公开（公告）日：2005-12-13
• 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.