4-methanesulfonyloxy-3-methoxybenzyl alcohol

• 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-methanesulfonyloxy-3-methoxybenzyl alcohol
• 英文别名: p-(hydroxymethyl)-2-methoxyphenyl methanesulfonate；Methanesulfonic acid 4-hydroxymethyl-2-methoxy-phenyl ester；[4-(hydroxymethyl)-2-methoxyphenyl] methanesulfonate
• 化学式: C₉H₁₂O₅S
• 分子量: 232.257
• InChiKey: UQZGDNZFPTYSAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methanesulfonyloxy-3-methoxybenzyl alcohol 在 2,2,6,6-四甲基哌啶氧化物 作用下， 以 叔丁醇 为溶剂， 以81%的产率得到4-methanesulfonyloxy-3-methoxybenzaldehyde
  参考文献：
  名称：

  TEMPO介导的微流控电解池中伯醇和仲醇的电氧化

  摘要：

  描述了2,2,6,6-四甲基哌啶-1-氧基（TEMPO）介导的修饰用于微流电解池的伯醇和仲醇电氧化的一般程序。电催化系统利用缓冲的叔丁醇水溶液反应介质，该介质可有效运行而无需额外的电解质，为在实验室规模的环境温度下将醇氧化为醛和酮提供了温和的方案。讨论了工艺的优化以及15种代表性醇的氧化。

  DOI：

  10.1002/cssc.201100601
• 作为产物：
  描述：

  4-methanesulfonyloxy-3-methoxybenzaldehyde 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 以81%的产率得到4-methanesulfonyloxy-3-methoxybenzyl alcohol
  参考文献：
  名称：

  A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

  摘要：

  sA low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency, and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin-related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multiphasic process for converting guaiacol to anisole and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate byproduct. Green chemistry aspects and the potential for industrial adoption are discussed.

  DOI：

  10.1021/acs.oprd.6b00314

文献信息

• Synthesis of <i>N</i> ‐alkylated pyrazolo[3,4‐ <i>d</i> ]pyrimidine analogs and evaluation of acetylcholinesterase and carbonic anhydrase inhibition properties
  作者：Busra O. Aydin、Derya Anil、Yeliz Demir

  DOI：10.1002/ardp.202000330

  日期：2021.5

  Fused pyrimidines, especially pyrazolo[3,4‐d]pyrimidines, are among the most preferred building blocks for pharmacology studies, as they exhibit a broad spectrum of biological activity. In this study, new derivatives of pyrazolo[3,4‐d]pyrimidine were synthesized by alkylation of the N1 nitrogen atom. We synthesized 3‐iodo‐1H‐pyrazolo[3,4‐d]pyrimidin‐4‐amine 2 from commercially available aminopyrazolopyrimidine

  稠合嘧啶，尤其是吡唑并[3,4- d ]嘧啶，是药理学研究中最优选的组成部分，因为它们表现出广泛的生物活性。本研究通过N1氮原子的烷基化合成了吡唑并[3,4- d ]嘧啶的新衍生物。我们合成了3-碘-1 ħ -吡唑并[3,4- d ]嘧啶-4-胺2由市售aminopyrazolopyrimidine 1使用Ñ碘代丁二酰亚胺作为碘化剂。化合物2的合成开始于3-iodo-1 H - pyrazolo[3,4- d的亲核取代]嘧啶-4-胺与R-X（X：-OMs，-Br，-Cl），得到 N-烷基化吡唑并[3,4- d ]嘧啶。我们使用弱无机碱进行这种合成，温和的温度也用于两步程序以生成N-烷基化吡唑并[3,4- d ]嘧啶衍生物。此外，还测试了所有化合物抑制乙酰胆碱酯酶 (AChE) 和人碳酸酐酶 (hCA) 异构体 I 和 II 的能力，ACh​​E 的K i值范围为 15.41 ± 1.39–63
• A Versatile Stereoselective Synthesis of <i>e</i><i>ndo,</i><i>e</i><i>xo</i>-Furofuranones:  Application to the Enantioselective Synthesis of Furofuran Lignans
  作者：Nigel A. Swain、Richard C. D. Brown、Gordon Bruton

  DOI：10.1021/jo035365r

  日期：2004.1.1

  key α-diazo-γ-butyrolactones 22−25. Highly stereoselective rhodium-catalyzed C−H insertion reactions of diazolactones 22−25 completed the synthesis of endo,exo-2,6-diarylfurofuranones 26−29 in overall yields ranging from 41 to 48% from 1-phenylallyl alcohol (±)-10. The approach developed for the furofuranones 26−29 was then applied to the asymmetric syntheses of four furofuran lignans, (+)-xanthoxylol

  使用Mn（III）介导的分子内环丙烷化和CH插入反应作为关键的CC键形成步骤，已开发出一种新的选择性内向-2,6-二芳基呋喃呋喃酮内酯的立体选择路线。Mn（III）介导的乙酰乙酸酯衍生物11的氧化环化反应提供了具有出色的非对映异构控制作用的1-乙酰基-4-芳基-3-氧杂双环[3.1.0]己-2-酮（12）（dr 22：1）。在激活的环丙烷环的存在随后的路易斯酸催化的开口12与苄醇然后给α乙酰-γ丁内酯16和18 - 20，其与原位生成的TFN有效地进行反应3来固定键α-重氮γ-丁内酯22 – 25。diazolactones的高度立体选择性铑催化的C-H插入反应22 - 25完成的合成内，外-2,6- diarylfurofuranones 26 - 29中的总产率，从1-苯基烯丙基醇范围从41到48％（±） - 10。用于furofuranones发展的方法，26 - 29（xanthoxylol
• TEMPO-Mediated Electrooxidation of Primary and Secondary Alcohols in a Microfluidic Electrolytic Cell
  作者：Joseph T. Hill-Cousins、Jekaterina Kuleshova、Robert A. Green、Peter R. Birkin、Derek Pletcher、Toby J. Underwood、Stuart G. Leach、Richard C. D. Brown

  DOI：10.1002/cssc.201100601

  日期：2012.2.13

  ne‐1‐oxyl (TEMPO)‐mediated electrooxidation of primary and secondary alcohols modified for application in a microfluidic electrolytic cell is described. The electrocatalytic system utilises a buffered aqueous tert‐butanol reaction medium, which operates effectively without the requirement for additional electrolyte, providing a mild protocol for the oxidation of alcohols to aldehydes and ketones at

  描述了2,2,6,6-四甲基哌啶-1-氧基（TEMPO）介导的修饰用于微流电解池的伯醇和仲醇电氧化的一般程序。电催化系统利用缓冲的叔丁醇水溶液反应介质，该介质可有效运行而无需额外的电解质，为在实验室规模的环境温度下将醇氧化为醛和酮提供了温和的方案。讨论了工艺的优化以及15种代表性醇的氧化。
• A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow
  作者：Yuhan Zhao、Georgina King、Maria H.T. Kwan、A. John Blacker

  DOI：10.1021/acs.oprd.6b00314

  日期：2016.11.18

  sA low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency, and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin-related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multiphasic process for converting guaiacol to anisole and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate byproduct. Green chemistry aspects and the potential for industrial adoption are discussed.