cordiachromene | 123164-53-4

• 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: cordiachromene
• 英文别名: cordiachromene A；2-Methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-ol；2-methyl-2-(4-methylpent-3-enyl)chromen-6-ol
• CAS: 123164-53-4
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: CEZCHPFUKBTQGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cordiachromene 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以23.4 mg的产率得到elaeagin
  参考文献：
  名称：

  Manners, Gary D., Journal of the Chemical Society. Perkin transactions I, 1983, # 1, p. 39 - 43

  摘要：

  DOI：
• 作为产物：
  描述：

  芳樟醇 在 palladium diacetate 、 三氯化铝 、 caesium carbonate 、 乙硫醇 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 4.0h， 生成 cordiachromene
  参考文献：
  名称：

  Synthesis of various 2H-benzopyran compounds and their kinetic resolution by asymmetric hydrolysis of their racemic acetates mediated by lipases

  摘要：

  The preparation of 2H-benzopyrans from bromophenols and tertiary allylic alcohols is described. The reaction is characterised by its mildness, good yields and ease of work-up. Kinetic resolution of the latter up to 95% ee was obtained by using enzyme-catalysed enantioselective hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00176-2

文献信息

• [EN] SYNTHESIS OF CHROMANE COMPOUNDS AND THEIR DERIVATIVES BY A COPPER-CATALYZED CONJUGATE ADDITION REACTION<br/>[FR] SYNTHÈSE DE COMPOSÉS DE CHROMANE ET DE LEURS DÉRIVÉS PAR UNE RÉACTION D'ADDITION CONJUGUÉE CATALYSÉE PAR DU CUIVRE
  申请人：DSM IP ASSETS BV

  公开号：WO2015059129A1

  公开（公告）日：2015-04-30

  The present invention relates to the preparation of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction. It has been observed that in highly stereoselective manner a methyl group can be introduced to the 2 position of chromane ring by reaction of a chromenone with Al(CH3)3 in the presence of a Cu(I) salt and specific chiral phosphoramidites. The compounds obtained are important intermediates particularly for the synthesis of chiral tocopherols.

  本发明涉及通过铜催化的共轭加成反应制备色满化合物及其衍生物。观察到，在高度立体选择性的方式下，通过色满酮与三甲基铝在铜(I)盐和特定手性磷酰胺的存在下反应，可以将甲基引入到色满环的2位。所得到的化合物是重要的中间体，特别适用于合成手性生育酚。
• Efficient Access to (All-<i>rac</i>)-α-Tocopherol Acetate by a Crombie Chromene Synthesis
  作者：Vincent Gembus、Nathalie Sala-Jung、Daniel Uguen

  DOI：10.1246/bcsj.82.843

  日期：2009.7.15

  In contrast to reports in the literature, the pyridine-catalysed condensation of phenolic compounds and conjugated aldehydes to chromenes was found to be applicable to trimethylhydroquinone 2a with the result of complementary convergent approaches to the title acetate using citral 3a and dihydromyrcene 9 as precursors of the phytyl residue.

  与文献中的报告相比，发现吡啶催化的酚类化合物与共轭醛类的缩合反应可以适用于三甲基氢醌2a，从而得到了利用香草醛3a和二氢美克烯9作为植基残基前体的互补聚合途径生成的目标醋酸酯。
• [EN] PROCESS OF SEPARATING CHIRAL ISOMERS OF CHROMAN COMPOUNDS AND THEIR DERIVATIVES AND PRECURSORS<br/>[FR] PROCÉDÉ DE SÉPARATION DES ISOMÈRES CHIRAUX DES COMPOSÉS DE CHROMANE, DE LEURS DÉRIVÉS ET PRÉCURSEURS
  申请人：DSM IP ASSETS BV

  公开号：WO2012152779A1

  公开（公告）日：2012-11-15

  The present invention relates to a process of separating chiral isomers of chroman compounds, particularly tocopherols and tocotrienols as well as the esters and intermediates thereof. It has been found that this process allows a separation of the desired isomer with a higher yield and enables the use of the non-desired isomers in a very efficient way. Said process is particularly useful when implemented in an industrial process. Furthermore, it has been found that this process allows using isomer mixtures as they result from traditional industrial synthesis.

  本发明涉及一种分离手性异构体的过程，特别是对于类胡萝卜素化合物中的生育酚和生育三烯酚以及它们的酯类和中间体。已经发现，该过程允许以更高的产率分离所需的异构体，并且能够非常有效地利用非所需的异构体。该过程在工业生产中实施时特别有用。此外，已经发现，该过程允许使用异构体混合物，因为它们是传统工业合成的结果。
• A short synthesis of cordiachromene
  作者：Philippe H. Kahn、Janine Cossy

  DOI：10.1016/s0040-4039(99)01728-1

  日期：1999.11

  Cordiachromene was synthesized from 5-methyl hept-5-en-2-one by using a Claisen rearrangement (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of chromane compounds and their derivatives by a copper-catalyzed conjugate addition reaction
  申请人：DSM IP Assets B.V.

  公开号：EP2865677B1

  公开（公告）日：2016-11-23