6-styryl-5,6-dihydro-γ-pyrone | 85613-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-styryl-5,6-dihydro-γ-pyrone
• 英文别名: styryldihydropyrone；2-(E-styryl)-2,3-dihydro-4H-pyran-4-one；2-styryl-2,3-dihydropyran-4-one；(E)-2-styryl-2H-pyran-4(3H)-one；(R)-2-E-Styryl-2,3-dihydro-4H-pyran4-one；2-[(E)-2-phenylethenyl]-2,3-dihydropyran-4-one
• CAS: 85613-04-3
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: FZAHUWLRLKATJP-VOTSOKGWSA-N

物化性质

• 沸点：
  322.4±32.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-styryl-5,6-dihydro-γ-pyrone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 以85%的产率得到(E)-2-styryl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

  摘要：

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.059
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 5.5h， 生成 6-styryl-5,6-dihydro-γ-pyrone
  参考文献：
  名称：

  On the scope, mechanism and stereochemistry of the Lewis acid catalyzed cyclocondensation of activated dienes with aldehydes: an application to the erythronolide problem

  摘要：

  DOI：

  10.1021/ja00291a026

文献信息

• A Lewis Base-catalyzed Hetero Diels–Alder Reaction between Aldehydes and the Danishefsky’s Diene
  作者：Teruaki Mukaiyama、Takayuki Kitazawa、Hidehiko Fujisawa

  DOI：10.1246/cl.2006.328

  日期：2006.3

  A lithium methoxide-catalyzed hetero Diels–Alder reaction of aromatic and aliphatic aldehydes with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky’s diene) is described. It proceeds through the Mukaiyama-Aldol reaction pathway and affords the corresponding 2,3-dihydropyran-4-one skeletons in good to excellent yields.

  报道了由甲醇锂催化的芳香醛和脂肪醛与1-甲氧基-3-三甲基硅氧基-1,3-丁二烯（Danishefsky双烯）的杂Diels-Alder反应。该反应通过Mukaiyama-Aldol反应途径进行，并以优异的产率获得了相应的2,3-二氢吡喃-4-酮骨架。
• On the mechanism of the lewis acid catalyzed cyclocondensation of aldehydes with siloxydienes
  作者：Eric R. Larson、Samuel Danishefsky

  DOI：10.1016/s0040-4039(00)87237-8

  日期：1982.1

  Competing cycloaddition versus aldolization-cyclization processes are demonstrated in the formation of 6-styryl-5,6-dihydro-y-pyronevia the BF3 catalyzed reaction of cinnamaldehyde with trans-1-methoxy 3-trimethylsilyloxy-1,3-butadiene.

  竞争性的环加成与醛醇缩合-环化过程通过肉桂醛与反式-1-甲氧基3-三甲基甲硅烷氧基-1,3-丁二烯的BF 3催化反应形成了6-苯乙烯基-5,6-二氢-吡喃酮。
• CHIRAL DISULFONIMIDES
  申请人：List Benjamin

  公开号：US20110313150A1

  公开（公告）日：2011-12-22

  Chiral disulfonimides having the formula I to III, wherein at least one of the groups A and B in the compound of formula I, C and D of the compound in formula II, and E and F of the compound in formula III is a chiral group, or E and F together form a chiral backbone, X is C, Si, O, N or S, and n is 0, 1, 2, 3, 4, 5 or 6, where n is >1 only if X is C, and G is as defined herein, and to the organic salts, metal salts and metal complexes thereof, are suited as NMR shift reagents and as reagents for racemate splitting, and also as chiral Brønsted acid catalysts or chiral Lewis acid catalysts for activating ketones, aldehydes and alkenes, and also as catalysts in the organic synthesis.

  拥有I至III式的手性二磺酰胺，其中在式I化合物中的A和B基团中至少有一个是手性基团，在式II化合物中的C和D以及在式III化合物中的E和F中，E和F可以共同形成一个手性骨架，X为C、Si、O、N或S，n为0、1、2、3、4、5或6，当X为C时n>1，G如本文所定义，并且适用于其有机盐、金属盐和金属配合物，作为NMR位移试剂和对消旋体分离的试剂，还可作为手性Brønsted酸催化剂或手性Lewis酸催化剂，用于活化酮、醛和烯烃，以及作为有机合成中的催化剂。
• Diiodosamarium, a catalyst precursor for diels-alder and hetero diels-alder reactions
  作者：Pierre van de Weghe、Jacqueline Collin

  DOI：10.1016/s0040-4039(00)77166-8

  日期：1994.4

  SmI2 presents catalystic activity for Diels-Alder reactions between cyclopentadiene or isoprene and various dienophiles, and for hetero Diels-Alder reactions.

  SmI 2对环戊二烯或异戊二烯与各种亲二烯体之间的Diels-Alder反应以及杂Diels-Alder反应具有催化活性。
• Competitive [2,3]- and [1,2]-Oxonium Ylide Rearrangements. Concerted or Stepwise?
  作者：Deana M. Jaber、Ryan N. Burgin、Matthew Helper、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1021/ol300213u

  日期：2012.4.6

  The axial equatorial conformational isomer distribution of the reactant diazoacetoacetate or its metal carbene intermediate is reflected in Rh(II) catalyzed oxonium ylide forming reactions of 3-(trans-2-arylvinyl)tetrahydropyranone-5-diazoacetoacetates that afford diastereoisomeric products for both the symmetry-allowed [2,3)- and the formally symmetry-forbidden [1,2]-oxonium ylide rearrangements.