2,3,6-trimethoxytoluene | 25576-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3,6-trimethoxytoluene
• 英文别名: 1,2,4-trimethoxy-3-methylbenzene；2-methyl-1,3,4-trimethoxybenzene；3-Methyl-1,2,4-trimethoxybenzene；2,3,6-trimethoxy-toluene；2,3,6-Trimethoxy-toluol；2,3,6-Trimethoxytoluol
• CAS: 25576-97-0
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: LGTNJVXAUPLFNU-UHFFFAOYSA-N

物化性质

• 熔点：
  30-31 °C
• 沸点：
  145-147 °C
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,6-trimethoxytoluene 在 二硫化碳 、 三氯化铝 、 硫酸 作用下， 生成 1.3.4-Trihydroxy-2-methyl-anthrachinon
  参考文献：
  名称：

  19.曲霉菌色素的化学性质。第一部分

  摘要：

  DOI：

  10.1039/jr9370000080
• 作为产物：
  描述：

  2,6-二甲氧基甲苯 在 dioxane*Br₂ 作用下， 生成 2,3,6-trimethoxytoluene
  参考文献：
  名称：

  Catechol O-methyltransferase. 9. Mechanism of inactivation by 6-hydroxydopamine

  摘要：

  A series of methylated analogues of 6-hydroxydopamine (6-OHDA) has been synthesized and evaluated as irreversible inhibitors of catechol O-methyltransferase (COMT). These analogues have been prepared in an effort to elucidate the mechanism involved in the inactivation of this enzyme by 6-OHDA. The analogues prepared had methyl groups incorporated in the 2 and/or 5 positions of 6-OHDA so as to block nucleophilic attakc at these positions in the corresponding oxidation products [6-hydroxydopamine-p-quinone (6-OHDAQ), aminochromes I and II]. Such 2- and/or 5-methylated 6-OHDA analogues were found to be inhibitors of COMT with the inactivation apparently resulting from modification of an essential amino acid residue at the active site of the enzyme. The activity of these analogues as inhibitors of COMT argues against a mechanism involving a 1,4 Michael addition reaction by a protein nucleophile at the 2 or 5 positions on 6-OHDAQ or on the corresponding aminochromes. Instead, an alternative mechanism is proposed to explain these data, which involves attack of a protein nucleophile at the carbonyl group in the 6 position of 6-OHDAQ or at the imine functionality on aminochromes I and II. The results of the present experiments have provided insight into the mechanism involved in inactivation of COMT by 6-OHDA. In addition, this study has provided considerable insight into the chemical reactivity of the electrophilic species generated after oxidation of 6-OHDA.

  DOI：

  10.1021/jm00232a007

文献信息

• Gold(I)-Catalyzed Intramolecular [4+2] Cycloadditions of Arylalkynes or 1,3-Enynes with Alkenes:  Scope and Mechanism
  作者：Cristina Nieto-Oberhuber、Patricia Pérez-Galán、Elena Herrero-Gómez、Thorsten Lauterbach、Cristina Rodríguez、Salomé López、Christophe Bour、Antonio Rosellón、Diego J. Cárdenas、Antonio M. Echavarren

  DOI：10.1021/ja075794x

  日期：2008.1.1

  The cyclizations of enynes substituted at the alkyne gives products of formal [4+2] cyclization with Au(I) catalysts. 1,8-Dien-3-ynes cyclize by a 5-exo-dig pathway to form hydrindanes. 1,6-Enynes with an aryl ring at the alkyne give 2,3,9,9a-tetrahydro-1H-cyclopenta[b]naphthalenes by a 5-exo-dig cyclization followed by a Friedel-Crafts-type ring expansion. A 6-endo-dig cyclization is also observed

  在炔烃上取代的烯炔环化得到正式的 [4+2] 环化产物与 Au(I) 催化剂。1,8-Dien-3-ynes 通过 5-exo-dig 途径环化形成hydrindanes。在炔烃上带有芳环的 1,6-烯炔通过 5-exo-dig 环化和 Friedel-Crafts 型环扩展得到 2,3,9,9a-四氢-1H-环戊 [b] 萘。在某些情况下，6-endo-dig 环化也被视为次要过程，尽管在少数情况下，这是主要的环化途径。除了带有大量联苯膦的阳离子金配合物外，具有三（2,6-二叔丁基苯基）亚磷酸酯的金配合物作为该反应的催化剂具有异常的反应活性。在微波辐射下加热也可以非常有效地进行这种环化。
• FULLERENE DERIVATIVE, AND METHOD OF PREPARING THE SAME
  申请人：YANAGAWA Yoshiki

  公开号：US20150158814A1

  公开（公告）日：2015-06-11

  A fullerene derivative having 60 or more carbon atoms, includes at least one specific structure.

  具有60个或更多碳原子的富勒烯衍生物包括至少一种特定结构。
• Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (−)-Elisabethadione
  作者：Paul S. O'Hora、Celia A. Incerti-Pradillos、Mikhail A. Kabeshov、Sergei A. Shipilovskikh、Aleksandr E. Rubtsov、Mark R. J. Elsegood、Andrei V. Malkov

  DOI：10.1002/chem.201500176

  日期：2015.3.16

  A new, highly efficient Lewis base catalyst for a practical enantio‐ and diastereoselective crotylation of unsaturated aldehydes with E‐ and Z‐crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (−)‐elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy‐Cope

  已开发出一种新型的高效路易斯碱催化剂，用于将不饱和醛与E-和Z-巴豆基三氯硅烷进行实际的对映异构和非对映异构的丁烯化。该方法被用作新的生物活性六氟烷二萜（-）-伊丽莎白乙二酮的不对称合成中的关键步骤。建立立体生成中心的其他战略反应包括阴离子氧化-Cope重排和阳离子环化。合成途径依赖于简单，高产率的反应，并且避免使用保护基或手性助剂。
• Synthesis of Polyfluoroalkyl Aza-Polycyclic Aromatic Hydrocarbons Enabled by Addition of Perfluoroalkyl Radicals onto Vinyl Azides
  作者：Yi-Feng Wang、Geoffroy Hervé Lonca、Maïwenn Le Runigo、Shunsuke Chiba

  DOI：10.1021/ol501997n

  日期：2014.8.15

  Radical perfluoroalkylation of α-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (Rf = CF3, C2F5, and C3F7) are employed as the sources of perfluoroalkyl radicals upon oxidation with PhI(OAc)2. The addition of perfluoroalkyl radicals to biarylvinyl azides generates the corresponding iminyl radicals, which

  α-（联芳基-2-基）乙烯基叠氮化物的自由基全氟烷基化能够提供多氟烷基氮杂-多环芳烃（氮杂-PAHs）。使用可商购获得的Me 3 SiR f（R f = CF 3，C 2 F 5和C 3 F 7）作为在用PhI（OAc）2氧化时的全氟烷基自由基的来源。将全氟烷基自由基加到联芳基乙烯基叠氮化物上产生相应的亚氨基自由基，其随后与分子内芳烃部分环化，从而提供具有多氟烷基（R f CH 2）功能的氮杂-PAH骨架。
• Boron trichloride as a selective demethylating agent for hindered ethers
  作者：Christopher F. Carvalho、Melvyn V. Sargent

  DOI：10.1039/c39840000227

  日期：——

  Boron trichloride has been found to be an efficient reagent for the selective cleavage of sterically hindered methoxy groups in methoxyarenes; the scope and utility of this reaction are explored.

  已发现三氯化硼是一种有效裂解甲氧基芳烃中位阻甲氧基的有效试剂。探索了该反应的范围和效用。