(6-methoxy-2,5,7,8-tetramethylchroman-2-yl)methanol | 184879-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6-methoxy-2,5,7,8-tetramethylchroman-2-yl)methanol
• 英文别名: (±)-6-methoxy-2,5,7,8-tetramethylchroman-2-methanol；3,4-dihydro-6-methoxy-2,5 ,7,8-tetramethyl-2H-benzopyran-2-methanol；(6-Methoxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methanol；(6-methoxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)methanol
• CAS: 184879-62-7
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: NFRJALHADOTRGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-methoxy-2,5,7,8-tetramethylchroman-2-yl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 6-methoxy-2,5,7,8-tetramethylchroman-2-carbaldehyde
  参考文献：
  名称：

  [EN] BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY
  [FR] ACTIVATEURS BIO-INSPIRÉS DES PROTÉASOMES AYANT UNE ACTIVITÉ ANTI-ÂGE

  摘要：

  本发明涉及新型生物启发的混合化合物，其化学式为I，作为蛋白酶体激活剂并具有抗衰老活性，以及其合成方法。这些混合化合物将羟基酪醇和天然抗氧化维生素E或其生物同系物的结构特征结合在一个分子支架中。化合物I的结构包括结构蛋白酶体激活剂（通过立体化学相互作用激活），可用于生产抗衰老产品，如化妆品制剂。此外，它们可以在蛋白酶体被下调的情况和疾病中使用，以及用作蛋白酶体激活控制化合物。

  公开号：

  WO2019171088A1
• 作为产物：
  描述：

  奎诺二甲基丙烯酸酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 49.0h， 生成 (6-methoxy-2,5,7,8-tetramethylchroman-2-yl)methanol
  参考文献：
  名称：

  脂质不饱和度、过氧自由基分配和色醇亲脂尾部如何影响 α-生育酚的抗氧化活性：通过使用荧光α-生育酚类似物进行的高通量荧光研究进行直接可视化

  摘要：

  据报道，制备了两种高度敏感的荧光 α-生育酚 (TOH) 类似物，它们在与过氧自由基反应后荧光强度增强 30 倍以上。探针由与 BODIPY 荧光团的中间位置耦合的色​​原醇部分组成，其中使用亚甲基接头（BODIPY-2,2,5,7,8-pentamethyl-6-hydroxy-chroman 加合物，H(2) B-PMHC) 与酯连接体 (meso-methanoyl BODIPY-6-hydroxy-2,5,7,8-tetramethylchromane-2-羧酸, H(2)B-TOH) 能够调整它们对 H 原子提取的反应性通过过氧自由基。随后描述了用于监测脂质体中过氧自由基反应动力学的高通量荧光测定的开发，其中荧光强度随时间的演变提供了快速、在 TOH 及其类似物存在下进行竞争动力学研究的简便方法。根据从各种生育酚类似物的 H 原子提取 (k(inh)) 的相对速率常数，为强度的时

  DOI：

  10.1021/ja301680m

文献信息

• Formation of sulfinate esters in the synthesis of triflates
  作者：Thomas Netscher、Patrick Bohrer

  DOI：10.1016/0040-4039(96)01930-2

  日期：1996.11

  and phenols with triflic anhydride in the presence of amines, trifluoromethanesulfinyl esters were unexpectedly found. Depending on the reaction conditions and the structures of both hydroxy compound and base, esterified products (yields <5% to 99%) containing 0% to 89% (!) of sulfinates were obtained. The mechanisms of these reactions are discussed. The results of the present study indicate how to

  在胺的存在下用三氟甲磺酸酐对空间拥挤的醇和苯酚进行标准处理时，出乎意料地发现了三氟甲亚磺酰基酯。根据反应条件以及羟基化合物和碱的结构，获得了包含0-89％（1）的亚磺酸盐的酯化产物（产率＜5％至99％）。讨论了这些反应的机理。本研究的结果表明如何避免在三氟甲磺酸酯合成中形成不必要的亚磺酸盐。
• Towards Highly Activating Leaving Groups: Studies on the Preparation of Some Halogenated Alkyl Sulfonates
  作者：Thomas Netscher、Patrick Bohrer

  DOI：10.3390/70800601

  日期：——

  The trichloromethylsulfonyl-, dichloromethylsulfonyl-, chlorosulfonyl-, and fluorosulfonyl esters of a neopentyl-type alcohol have been prepared via sulfonylation or sulfinylation followed by oxidation. The preparative usefulness and potential of the transformations are discussed.

  新戊基型醇的三氯甲基磺酰基-、二氯甲基磺酰基-、氯磺酰基-和氟磺酰基酯已通过磺酰化或亚磺酰化随后氧化制备。讨论了转换的准备用途和潜力。
• Microwave-assisted synthesis of 3,5-disubstituted isoxazoles and evaluation of their anti-ageing activity
  作者：Maria Koufaki、Theano Fotopoulou、Marianna Kapetanou、Georgios A. Heropoulos、Efstathios S. Gonos、Niki Chondrogianni

  DOI：10.1016/j.ejmech.2014.06.046

  日期：2014.8

  One-pot uncatalysed microwave-assisted 1,3-dipolar cycloaddition reactions between in situ generated nitrile oxides and alkynes bearing protected antioxidant substituents, were regioselectively afforded 3,5-disubstituted isoxazoles. The yields were moderate, based on the starting aldehydes, while the reaction times were in general shorter than those reported in the literature. The cytoprotective and anti-ageing effect of the final deprotected compounds was evaluated in vitro, on cellular survival following oxidative challenge and in vivo, on organismal longevity using the nematode Caenorhabditis elegans. The activity of the isoxazole analogues depends on the nature and the number of the antioxidant substituents. Analogue 17 bearing a phenolic group and a 6-OH-chroman group is a promising anti-ageing agent, since it increased survival of human primary fibroblasts following treatment with H2O2 and extended C. elegans lifespan.
• A New Tactic for Tocopherol Synthesis Using Intramolecular Benzyne Trapping by an Alcohol
  作者：David W. Knight、Qing Xu

  DOI：10.3987/com-15-s(t)52

  日期：——

  A formal total synthesis of (S)-alpha-tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-amination using an oxaziridine; chiral, nonracemic intermediates are generated using asymmetric dihydroxylation.This paper is dedicated to Professor Lutz Tietze on his 75th birthday, with all best wishes.
• A synthesis of α-tocopherol featuring benzyne trapping by an alcohol
  作者：David W. Knight、Xu Qing

  DOI：10.1016/j.tetlet.2009.03.022

  日期：2009.7

  A formal total synthesis of alpha-tocopherol, the main component of Vitamin E, has been achieved in which a central step is the intramolecular trapping of a highly substituted benzyne by an alcohol group to establish the pyran ring. (C) 2009 Elsevier Ltd. All right reserved.