2-丙烯基芝麻酚 | 193757-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 2-丙烯基芝麻酚
• 英文名称: 4,5-methylenedioxy-2-(1-propenyl)phenol
• 英文别名: 6-(prop-1-enyl)-1,3-benzodioxol-5-ol；2-propenylsesamol；6-Prop-1-enyl-1,3-benzodioxol-5-ol
• CAS: 193757-32-3
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: DHBXSKXIJDFPSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-丙烯基芝麻酚 在 Mo(CHCMe2Ph)2 、 四丁基硫酸氢铵 、 lead(II) chloride sodium hydroxide 、 四甲基乙二胺 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 苯 为溶剂， 反应 47.0h， 生成 2-(2',4'-dibenzyloxyphenyl)-5,6-methylenedioxybenzofuran
  参考文献：
  名称：

  The Synthesis of Cyclic Enol Ethers via Molybdenum Alkylidene-Catalyzed Ring-Closing Metathesis

  摘要：

  An efficient method for the construction of five- and six-membered cyclic vinyl ethers from unsaturated esters using stoichiometric titanium reagents to convert the esters to acyclic olefinic enol ethers which are then transformed to the desired products by catalytic ring-closing olefin metathesis with a molybdenum alkylidene complex is described.

  DOI：

  10.1021/jo00094a002
• 作为产物：
  描述：

  5-hydroxy-6-(2-propenyl)-1,3-benzodioxole 在 immobilised version of Felkin's iridium catalyst 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到2-丙烯基芝麻酚
  参考文献：
  名称：

  使用固体负载试剂和清除剂简明合成天然产物卡帕酮

  摘要：

  聚合物支持的试剂已应用于天然产物卡帕酮的合成，无需常规纯化技术即可实现清洁高效的合成。

  DOI：

  10.1055/s-2001-16783

文献信息

• A Polymer-supported Iridium Catalyst for the Stereoselective Isomerisation of Double Bonds
  作者：Ian R. Baxendale、Ai-Lan Lee、Steven V. Ley

  DOI：10.1055/s-2002-20483

  日期：——

  A polymer-supported iridium catalyst has been prepared and used in the isomerisation of the double bonds in aryl allylic derivatives with excellent trans selectivity and without the need for conventional work-up procedures.

  一种聚合物负载的铱催化剂已经被制备出来，并用于芳基烯丙基衍生物中双键的异构化过程，具有优异的反式选择性，且无需传统后处理步骤。
• Silver-Catalyzed Asymmetric Synthesis of 2,3-Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans
  作者：Leticia Jiménez-González、Sergio García-Muñoz、Miriam Álvarez-Corral、Manuel Muñoz-Dorado、Ignacio Rodríguez-García

  DOI：10.1002/chem.200600332

  日期：2006.11.24

  of fluoride ion. The application of this strategy by using chiral catalysts leads to a new enantioselective total synthesis of natural cis-pterocarpans and their trans isomers. Through this method, the first enantioselective total synthesis of the antifungal agent (-)-pterocarpin was achieved. In addition, a new entry into the heteroaromatic system of 2,5-dihydrobenzoxepine is also presented.

  2,3-二氢苯并呋喃可以在Ag（I）配合物的催化下，在氟离子源的存在下，通过芳族醛与2,3-二氢苯并西拉西平的缩合，非对映选择性地制备。通过使用手性催化剂应用该策略导致了天然顺式-罗汉果及其反式异构体的新的对映选择性全合成。通过该方法，实现了抗真菌剂（-）-罗哌卡丁的首次对映选择性全合成。另外，还提出了新的进入2，5-二氢苯并己平杂芳族体系的方法。
• A Concise Synthesis of the Natural Product Carpanone Using Solid-Supported Reagents and Scavengers
  作者：Ian R. Baxendale、Ai-Lan Lee、Steven V. Ley

  DOI：10.1055/s-2001-16783

  日期：——

  Polymer-supported reagents have been applied to the synthesis of the natural product carpanone resulting in a clean and efficient synthesis without the requirement for conventional purification techniques.

  聚合物支持的试剂已应用于天然产物卡帕酮的合成，无需常规纯化技术即可实现清洁高效的合成。
• A New Catalytic Cu(II)/Sparteine Oxidant System for β,β-Phenolic Couplings of Styrenyl Phenols: Synthesis of Carpanone and Unnatural Analogs
  作者：R. Nathan Daniels、Olugbeminiyi O. Fadeyi、Craig W. Lindsley

  DOI：10.1021/ol801643t

  日期：2008.9.18

  A new catalytic Cu(II)/sparteine system has been developed to promote beta,beta-phenolic couplings of styrenyl phenols en route to carpanone and related unnatural congeners in yields exceeding 85%.
• Oxidative Dimerization of (<i>E</i>)- and (<i>Z</i>)-2-Propenylsesamol with O₂ in the Presence and Absence of Laccases and Other Catalysts: Selective Formation of Carpanones and Benzopyrans under Different Reaction Conditions
  作者：Mihaela-Anca Constantin、Jürgen Conrad、Elena Merişor、Katja Koschorreck、Vlada B. Urlacher、Uwe Beifuss

  DOI：10.1021/jo300263k

  日期：2012.5.18

  The oxidative dimerization of 2-propenylsesamol to carpanone with O-2 as the oxidant, which probably proceeds as a domino phenol oxidation/anti-beta,beta-radical coupling/intramolecular hetero Diets-Alder reaction, can be efficiently catalyzed by laccases. Experiments with laccases and other catalysts like a Co(salen) type catalyst and PdCl2 clearly demonstrate that the diastereoselectivity of the carpanone formation does not depend on the catalyst but on the double-bond geometry of the substrate. With (E)-2-propenylsesamol as the substrate, carpanone and a so far unknown carpanone diastereoisomer are formed in a 9:1 ratio. When (Z)-2-propenylsesamol is used as starting material, carpanone is accompanied by two carpanone diastereoisomers unknown so far in a 5:1:4 ratio. All three carpanone diastereoisomers have been separated by HPLC, and their structures have been elucidated unambiguously by NMR spectroscopy, DFT calculations, and spin work analysis. When the oxidation of 2-propenylsesamol with O-2 is performed in the absence of any catalyst two diastereoisomeric benzopyrans are formed, probably as the result of a domino oxidation/intermolecular hetero Diets-Alder reaction. Under these conditions, carpanone is formed in trace amounts only.