allyl 3,5-bis(allyloxy)benzoate | 189684-08-0

• 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: allyl 3,5-bis(allyloxy)benzoate
• 英文别名: prop-2-enyl 3,5-bis(prop-2-enoxy)benzoate
• CAS: 189684-08-0
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: RIGKJYIWZLKFKV-UHFFFAOYSA-N

物化性质

• 沸点：
  382.4±37.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  allyl 3,5-bis(allyloxy)benzoate 在 lithium aluminium tetrahydride 、 扁桃腈裂解酶来源于杏仁 、 硫酸 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 异丙醚 、 溶剂黄146 为溶剂， 反应 49.0h， 生成 (R)-2-acetoxy-2-(3,5-bis(allyloxy)phenyl)-N-tert-butylacetamide
  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：

  3,5-二羟基苯甲酸 、 3-溴丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 allyl 3,5-bis(allyloxy)benzoate
  参考文献：
  名称：

  混合硫醇-烯/炔反应中的端基作为多酶响应聚合两亲物的简单方法

  摘要：

  利用硫醇-烯和硫醇-炔化学的高保真度，我们使用硫醇的混合物制备了可降解的 PEG-树枝状两亲物，其功能化了两种不同类型的酶促可裂解端基。通过调整两种硫醇的进料比，我们实现了具有统计上不同端基比例的杂化物的混合物。统计混合杂交体的分解研究表明，当与每种活化酶一起孵育时，这些两亲物具有更高程度的响应，而对于两种不同两亲物的对照混合物观察到更高程度的选择性，这需要两种类型的存在酶进行完全分解。

  DOI：

  10.1055/s-0037-1611340

文献信息

• Contrast media
  申请人：Amersham Health AS

  公开号：US06448442B1

  公开（公告）日：2002-09-10

  The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents of formula I wherein n is 0 or 1, and where n is 1 each C6R5 moiety may be the same or different; X denotes a bond or a group providing a 1 to 7 atom chain linking two C6R5 moieties or, where n is 0, X denotes a group R; each group R is a hydrogen atom, an iodine atom or a hydrophilic moiety M or M1, two or three non-adjacent R groups in each C6R5 moiety being iodine and at least one R group in each C6R5 moiety being an M or M1 moiety; each M which may be the same or different, is a non-ionic hydrophilic moiety; and each M1 independently represents a —CHOHCON(R1)2 group wherein each R1, which may be the same or different, is a hydrogen atom, an OH group or a C1-6 alkoxy or optionally hydroxylated C1-5 alkyl group; at least one R group in the molecule being an M1 moiety; and isomers thereof.

  该发明提供了低粘度碘化芳基化合物，作为公式I的X射线造影剂，其中n为0或1，当n为1时，每个C6R5基团可以相同也可以不同；X表示连接两个C6R5基团的1至7个原子链的键或基团，或者当n为0时，X表示基团R；每个基团R是氢原子、碘原子或亲水基团M或M1，每个C6R5基团中的两个或三个非相邻的R基团为碘，且每个C6R5基团中至少一个R基团为M或M1基团；每个M可以相同也可以不同，是非离子性亲水基团；每个M1独立地表示一个—CHOHCON(R1)2基团，其中每个R1可以相同也可以不同，是氢原子、羟基或C1-6烷氧基或选择性羟基化的C1-5烷基基团；分子中至少一个R基团为M1基团；以及其异构体。
• Iodinated x-ray contrast media
  申请人：Nycomed Imaging AS

  公开号：US06310243B1

  公开（公告）日：2001-10-30

  The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula C6R6 wherein three non-adjacent R groups are iodine and the remaining R groups are non-ionic, hydrophilic moieties, said compound being water soluble at 20° C. to a concentration of at least 350 mgl/ml and which in aqueous solution at 20° C. at a concentration of 350 mgl/ml has a viscosity no greater than 13.8 mPas.

  该发明提供了低粘度碘化芳基化合物，可用作X射线造影剂，其化学式为C6R6，其中三个非相邻的R基团为碘，其余的R基团为非离子、亲水基团，所述化合物在20°C时可溶于水，浓度至少为350 mgl/ml，在20°C时在水溶液中浓度为350 mgl/ml时，粘度不大于13.8 mPas。
• 스즈키 커플링 반응을 이용한 모라신 F 합성방법
  申请人：Industry Academic Cooperation Foundation, Hallym University 한림대학교 산학협력단(220070195175) BRN ▼221-82-10284

  公开号：KR101778964B1

  公开（公告）日：2017-09-18

  해결하려는 과제: 생물학적 활성을 가진 천연 화합물 모라신 F를 합성하는 방법을 제공하는 것. 과제 해결수단: 본 발명자들은 상업적으로 입수 가능한 출발물질로부터 스즈키 커플링 반응을 핵심 단계로 이용하여 생물학적 활성을 가진 모라신 F를 효율적으로 합성할 수 있다.

  任务：提供合成具有生物活性的天然化合物莫拉信F的方法。解决方法：本发明人利用可商业获取的起始物质，通过铃木偶联反应作为关键步骤，可以高效地合成具有生物活性的莫拉信F。
• Diversity Oriented Synthesis of Natural 2-Arylbenzofuran, Moracin F
  作者：So-Ra Yun、Jong-Gab Jun

  DOI：10.1002/bkcs.10847

  日期：2016.8

  Diversity oriented synthesis of natural 2‐arylbenzofuran, moracin F (1) has been carried out from the commercially available starting materials using Sonogashira coupling, Suzuki coupling, neutral Al2O3 mediated cyclization, and intramolecular Wittig reaction as key steps.

  使用Sonogashira偶联，Suzuki偶联，中性Al 2 O 3介导的环化和分子内Wittig反应作为关键步骤，已经从市售的起始原料中进行了面向天然的2-芳基苯并呋喃，草精F（1）的多样性导向合成。
• 소노가시라 커플링 반응을 이용한 모라신 F 합성방법
  申请人：Industry Academic Cooperation Foundation, Hallym University 한림대학교 산학협력단(220070195175) BRN ▼221-82-10284

  公开号：KR101739728B1

  公开（公告）日：2017-05-25

  해결하려는 과제: 생물학적 활성을 가진 천연 화합물 모라신 F를 합성하는 방법을 제공하는 것. 과제 해결수단: 본 발명자들은 상업적으로 입수 가능한 출발물질로부터 소노가시라 커플링 반응을 핵심 단계로 이용하여 생물학적 활성을 가진 모라신 F를 효율적으로 합성할 수 있다.

  解决的问题：提供合成具有生物活性的天然化合物莫拉信F的方法。解决方法：本发明者利用商业上可获得的起始物质，通过索诺加斯里偶联反应作为关键步骤，可以高效地合成具有生物活性的莫拉信F。