8-azido-3,6-dioxaoctyl thioacetate | 178685-34-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 8-azido-3,6-dioxaoctyl thioacetate
• 英文别名: S-[2-[2-(2-azidoethoxy)ethoxy]ethyl] ethanethioate
• CAS: 178685-34-2
• 化学式: C₈H₁₅N₃O₃S
• 分子量: 233.291
• InChiKey: QGLYXWXSTVAYAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-azido-3,6-dioxaoctyl thioacetate 在 sodium methylate 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 48.67h， 生成 (9H-fluoren-9-yl)methyl (2-(4-(3-((2-(2-(2-azidoethoxy)ethoxy)ethyl)thio)propyl)-5-hydroxy-1H-indol-3-yl)ethyl)carbamate
  参考文献：
  名称：

  Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support

  摘要：

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.

  DOI：

  10.1021/jo2025477
• 作为产物：
  描述：

  2-(2-(2-azidoethoxy)ethoxy)ethyl methanesulfonate 、 potassium thioacetate 以 乙醇 为溶剂， 以90%的产率得到8-azido-3,6-dioxaoctyl thioacetate
  参考文献：
  名称：

  Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support

  摘要：

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.

  DOI：

  10.1021/jo2025477

文献信息

• SULFORAPHANE-DERIVED COMPOUNDS, PRODUCTION METHOD THEREOF AND THE MEDICAL, FOOD AND COSMETIC USE OF SAME
  申请人：Consejo Superior De Investigaciones CientÍficas (CSIC)

  公开号：US20150110863A1

  公开（公告）日：2015-04-23

  The present invention relates to a new series of compounds having general formula (I) and the optical isomer or enantiomer forms thereof, which belong to the family of sulforaphane derivatives. The invention also relates to the production method thereof. The invention further relates to the multiple medical (pharmaceutical, homeopathic and phytotherapeutic), food, cosmetic and dietary uses of said series of compounds, especially the use thereof in the prevention and/or treatment of diseases and any type of illness or damage associated with an oxidative process or which, although not involved in said process, are mediated by the Nrf2 transcription factor, such as, for example, cancer. The compounds can be used alone or, alternatively, encapsulated in cyclodextrins.

  本发明涉及具有一般式(I)及其光学异构体或对映体形式的新系列化合物，属于硫代异硫氰酸酯衍生物家族。该发明还涉及其生产方法。此发明还涉及该系列化合物的多种医学（药用、顺势疗法和植物疗法）、食品、化妆品和膳食用途，特别是在预防和/或治疗与氧化过程相关的疾病和任何类型的疾病或损伤方面的使用，或者虽然不涉及该过程，但受Nrf2转录因子介导，例如癌症。这些化合物可以单独使用，或者被包埋在环糊精中。
• GRGDS-Functionalized Poly(lactide)-<i>graft</i>-poly(ethylene glycol) Copolymers: Combining Thiol–Ene Chemistry with Staudinger Ligation
  作者：Dorothee E. Borchmann、Niels ten Brummelhuis、Marcus Weck

  DOI：10.1021/ma4005633

  日期：2013.6.11

  A tri(ethylene glycol)-containing lactide analogue was synthesized via thiol–ene chemistry between a bifunctional triethylene glycol and allyl lactide. Subsequent tin octoate catalyzed ring-opening polymerization yielded well-defined poly(lactide)-graft-poly(ethylene glycol) copolymers with molecular weights of 6 × 103 g/mol and polydispersity indices of 1.6. The tri(ethylene glycol) chains along the

  通过双功能三甘醇和烯丙交酯之间的硫醇-烯化学合成了含有三（乙二醇）的丙交酯类似物。随后的辛酸锡催化的开环聚合产生了明确定义的聚（丙交酯）-接枝-聚（乙二醇）共聚物，其分子量为 6 × 10 3  g/mol，多分散指数为 1.6。沿着共聚物的三（乙二醇）链包含能够进行有效的聚合后官能化的叠氮化物末端。该策略的效用通过成功的 Staudinger 连接来安装 Gly-Arg-Gly-Asp-Ser (GRGDS) 肽得到证明。
• US9884816B2
  申请人：——

  公开号：US9884816B2

  公开（公告）日：2018-02-06
• Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support
  作者：Erik Daa Funder、Anne Bjørnskov Jensen、Thomas Tørring、Anne Louise Bank Kodal、Ane Rebolledo Azcargorta、Kurt Vesterager Gothelf

  DOI：10.1021/jo2025477

  日期：2012.4.6

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.