(-)-(R)-Cordiachromene

• 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: (-)-(R)-Cordiachromene
• 英文别名: (2R)-(+)-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-6-ol；(2R)-2-methyl-2-(4-methylpent-3-enyl)chromen-6-ol
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: CEZCHPFUKBTQGN-MRXNPFEDSA-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

• 作为产物：
  描述：

  芳樟醇 在 甲醇 、 4-二甲氨基吡啶 、 palladium diacetate 、 三氯化铝 、 potassium carbonate 、 caesium carbonate 、 三乙胺 、 乙硫醇 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 12.05h， 生成 (-)-(R)-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。
• Enantioselective 6-endo-trig Wacker-type cyclization of 2-geranylphenols: application to a facile synthesis of (−)-cordiachromene
  作者：Kazuhiro Takenaka、Yugo Tanigaki、Mahesh L. Patil、C.V. Laxman Rao、Shinobu Takizawa、Takeyuki Suzuki、Hiroaki Sasai

  DOI：10.1016/j.tetasy.2010.04.060

  日期：2010.4

  An enantioselective intramolecular oxidative cyclization of 2-geranylphenols catalyzed by a Pd(II)-spiro bis(isoxazoline) complex is reported. The reaction proceeds in a 6-endo-trig manner to give chromene derivatives in reasonable yields and with moderate enantioselectivities. This transformation can be applied to a protecting-group-free total synthesis of naturally occurring cordiachromene.

  报道了Pd（II）-螺双（异恶唑啉）配合物催化的2-香叶基酚的对映选择性分子内氧化环化。反应以6-内-触发方式进行，以合理的收率和适度的对映选择性得到色烯衍生物。该转化可以应用于天然存在的堇青色烯的无保护基的全合成。
• Enantioselective Synthesis of (−)-(<i>R</i>)-Cordiachromene and (−)-(<i>R</i>)-Dictyochromenol Utilizing Intramolecular<i>S</i>_NAr Reaction
  作者：Yoshihiro Noda、Misato Yasuda

  DOI：10.1002/hlca.201200312

  日期：2012.10

  A simple and efficient enantioselective synthesis of chromene, (−)‐(R)‐cordiachromene (1), and (−)‐(R)‐dictyochromenol (2) has been accomplished. This convergent synthesis utilizes intramolecular SNAr reaction for the formation of chroman ring, and Seebach's method of ‘self‐reproduction of chirality’ should establish the (R)‐configuration of the C(2) side chain as key steps.

  一个简单而有效的对苯二酚，（-）-（R）-cordiachromene（1）和（-）-（R）-dictyochromenol（2）的对映选择性合成已经完成。这种聚合合成利用分子内的S N Ar反应形成苯并二氢吡喃环，Seebach的“手性自我复制”方法应将C（2）侧链的（R）-构型确立为关键步骤。
• 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
• Enantioselective Synthesis of Cordiachromene
  作者：Samir Bouzbouz、Jean-Yves Goujon、Jerôme Deplanne、Bernard Kirschleger

  DOI：10.1002/1099-0690(200009)2000:18<3223::aid-ejoc3223>3.0.co;2-l

  日期：2000.9