2-(1'-hydroxy-1'-methylethyl)-5-methylfuran | 80828-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(1'-hydroxy-1'-methylethyl)-5-methylfuran
• 英文别名: 2-(5-methyl-2-furanyl)-2-propanol；2-(5-methylfuran-2-yl)propan-2-ol；2-(5-methyl-[2]furyl)-propan-2-ol
• CAS: 80828-39-3
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: XXMJEVAPHZUYBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1'-hydroxy-1'-methylethyl)-5-methylfuran 在 双氧水 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 7.0h， 以77%的产率得到6-hydroperoxy-2,2,6-trimethyl-2H-pyran-3(6H)-one
  参考文献：
  名称：

  New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions

  摘要：

  Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used Lis oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)(4)/L-DET or Ti(O-i-Pr)(4)/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomierically enriched Ti(IV)/BINOL/H2O complexes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00326-9
• 作为产物：
  描述：

  2-甲基呋喃 在 乙醚 、 四氯化锡 作用下， 生成 2-(1'-hydroxy-1'-methylethyl)-5-methylfuran
  参考文献：
  名称：

  Fetizon; Baranger, Bulletin de la Societe Chimique de France, 1957, p. 1311,1315

  摘要：

  DOI：

文献信息

• POLYSUBSTITUTED DERIVATIVES OF 6-HETEROARYLIMIDAZO[1,2-a]PYRIDINES, AND PREPARATION AND THERAPEUTIC USE THEREOF
  申请人：DE PERETTI Danielle

  公开号：US20110065700A1

  公开（公告）日：2011-03-17

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , Het and X are as defined in the disclosure, or an acid addition salt thereof, and the therapeutic use and process of synthesis thereof.

  式(I)的化合物： 其中R1、R2、R3、R4、Het和X如披露中所定义，或其酸盐加合物，以及其治疗用途和合成过程。
• Formal Synthesis of (−)-Englerin A and Cytotoxicity Studies of Truncated Englerins
  作者：Jing Xu、Eduardo J. E. Caro-Diaz、Ayse Batova、Steven D. E. Sullivan、Emmanuel A. Theodorakis

  DOI：10.1002/asia.201101021

  日期：2012.5

  An efficient formal synthesis of (−)‐englerin A (1) is reported. The target molecule is a recently isolated guaiane sesquiterpene that possesses highly potent and selective activity against renal cancer cell‐lines. Our enantioselective strategy involved the construction of the BC ring system of compound 1 through a RhII‐catalyzed [4+3] cycloaddition reaction followed by subsequent attachment of the

  报道了 (-)-englerin A ( 1 )的有效形式合成。目标分子是最近分离的愈创木酚倍半萜烯，它对肾癌细胞系具有高效和选择性的活性。我们的对映选择性策略涉及通过 Rh II构建化合物1的 BC 环系统-催化的 [4+3] 环加成反应，随后通过分子内醛醇缩合反应连接 A 环。因此，该策略允许合成截断的 englerins。用 A498 肾癌细胞系对这些类似物进行评估表明，englerin 的 A 环对其抗增殖活性至关重要。此外，对这些类似物的评估导致鉴定了 CEM 细胞的强效生长抑制剂，其 GI 50值在 1-3 μM范围内。
• Synthetic Approach to Analogues of the Original Structure of Sclerophytin A
  作者：Michael E. Jung、Joseph Pontillo

  DOI：10.1021/jo016246j

  日期：2002.9.1

  is described. The beta-anomer of dideoxyribosyl nitriles 10a,b (prepared from glutamic acid) was converted into the methyl ketone 11. Addition of a silylated acetylide to 11 in diethyl ether/trimethylamine gave mainly 22a. Alkylation with methallyl halide and ozonolysis gave the ketone 24, which was then converted by hydrogenation and a second ozonolysis into the keto aldehyde 26. A two-step aldol process

  描述了硬化菌素A的原始结构的类似物的途径。将双脱氧核糖基腈10a，b的β-端基异构体（由谷氨酸制备）转化为甲基酮11。在乙醚/三甲胺中将甲硅烷基化的乙炔化物加到11上，主要得到22a。用甲基烯丙基卤化物烷基化并进行臭氧分解，得到酮24，然后通过氢化和第二次臭氧分解将其转化为酮醛26。两步的醇醛缩醛工艺以良好的总产率提供了所需的3-吡喃酮27。然而，几种将该烯酮27转化为所需的菌藻素类似物2的方法失败了。
• The first enzymatic Achmatowicz reaction: selective laccase-catalyzed synthesis of 6-hydroxy-(2H)-pyran-3(6H)-ones and (2H)-pyran-2,5(6H)-diones
  作者：Chimène Asta、Dietmar Schmidt、Jürgen Conrad、Bernhard Förster-Fromme、Till Tolasch、Uwe Beifuss

  DOI：10.1039/c3ra44107e

  日期：——

  laccase-catalyzed oxidation of (5-alkylfuran-2-yl)carbinols using aerial oxygen as an oxidant selectively affords 6-hydroxy-(2H)-pyran-3(6H)-ones with yields up to 90%. With suitable substituted furan-2-yl carbinols as substrates the procedure allows the efficient preparation of (2H)-pyran-2,5(6H)-diones in a single step.

  使用空气中的氧气作为氧化剂的漆酶催化的（5-烷基呋喃-2-基）甲醇的氧化选择性生成6-羟基-（2 H）-吡喃-3（6 H）-一，收率高达90％。以合适的取代的呋喃-2-基甲醇为底物，该方法允许在一个步骤中高效制备（2 H）-吡喃-2,5（6 H）-二酮。
• Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds
  作者：Dimitris Noutsias、Ioanna Alexopoulou、Tamsyn Montagnon、Georgios Vassilikogiannakis

  DOI：10.1039/c2gc16397g

  日期：——

  A new set of completely green methods utilising air, light, water and spirulina to transform readily accessible furan substrates into a diverse range of synthetically useful polyoxygenated motifs commonly found in natural products is presented herein.

  本文介绍了一套全新的绿色方法，利用空气、光、水和螺旋藻将易获得的呋喃底物转化为在天然产物中常见的多种合成上有用的多氧官能团结构单元。