3,5-dibenzylidene-tetrahydropyran-4-one | 62513-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 3,5-dibenzylidene-tetrahydropyran-4-one
• 英文别名: tetrahydro-3,5-bis-(phenylmethylene)-4H-pyran-4-one；tetrahydro-3,5-bis(phenylmethylene)-4H-pyran-4-one；3,5-dibenzylideneoxan-4-one
• CAS: 62513-33-1
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: BYUOXPBVJAPZNL-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  486.3±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3,5-dibenzylidene-tetrahydropyran-4-one 、 1-methyl-4-(benzylsulfonyl)benzene 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 以78%的产率得到(1S,2R,6R,7S)-1,2,6,7-tetraphenyl-9-oxadispiro[2.1.25.33]decan-4-one
  参考文献：
  名称：

  Synthesis of diarylcyclopropyl spirocyclic ketones

  摘要：

  A facile one-pot synthetic route for preparing a series of functionalized diarylcyclopropyl spirocyclic ketones 4 is developed. The efficient cyclopropanation route of the conjugated cyclic ketones 2 with sulfones 1 in the presence of NaH shows interesting molecular diversities. The reaction mechanism of the stereocontrolled cyclopropanations has been discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.056
• 作为产物：
  描述：

  四氢吡喃酮 、 苯甲醛 在 lithium perchlorate 、 三甲基硅烷基二乙胺 作用下， 反应 3.0h， 以91%的产率得到3,5-dibenzylidene-tetrahydropyran-4-one
  参考文献：
  名称：

  高氯酸锂介导的首次高效合成双（芳基亚甲基）吡喃酮

  摘要：

  摘要 本文描述了在无溶剂条件下，在（三甲基甲硅烷基）二乙胺和高氯酸锂存在下，四氢吡喃-4-酮与多种芳香醛在室温下的非常有效的双交羟醛缩合反应。3,5-双（芳基亚甲基）吡喃酮的高产率是通过简单的一锅通用程序实现的。

  DOI：

  10.1080/00397910500334447

文献信息

• Organocatalytic Conjugate Addition of Malononitrile to Conformationally Restricted Dienones
  作者：Zhi-Peng Hu、Chun-Liang Lou、Jin-Jia Wang、Chun-Xia Chen、Ming Yan

  DOI：10.1021/jo200112r

  日期：2011.5.20

  Organocatalytic conjugate addition of malononitrile to conformationally restricted dienones has been studied. A series of chiral primary and tertiary amine catalysts were screened. A piperidine-based thiourea-tertiary amine was found to be the efficient catalyst. Chiral pyran derivatives were obtained in excellent yields and enantioselectivities via a cascade conjugate addition–intramolecular cyclization pathway

  已经研究了丙二腈向构象受限的二烯酮的有机催化共轭加成。筛选了一系列手性伯胺和叔胺催化剂。发现基于哌啶的硫脲叔胺是有效的催化剂。通过级联共轭加成-分子内环化途径获得了高收率和对映选择性的手性吡喃衍生物。对于构象柔性二烯酮的相应反应，该反应明显不同。
• First Highly Efficient Synthesis of bis(Arylmethylidene)pyranones Mediated by Lithium Perchlorate
  作者：M. Saeed Abaee、Mohammad M. Mojtahedi、M. Mehdi Zahedi、S. Mohammad Bolourtchian

  DOI：10.1080/00397910500334447

  日期：2006.2.1

  Abstract A remarkably efficient double‐crossed aldol condensation of tetrahydropyran‐4‐one with a variety of aromatic aldehydes is described at room temperature in the presence of (trimethylsilyl)diethylamine and lithium perchlorate under solvent‐free conditions. Excellent yields of 3,5‐bis(arylmethylidene)pyranones are achieved in a facile one‐pot general procedure.

  摘要 本文描述了在无溶剂条件下，在（三甲基甲硅烷基）二乙胺和高氯酸锂存在下，四氢吡喃-4-酮与多种芳香醛在室温下的非常有效的双交羟醛缩合反应。3,5-双（芳基亚甲基）吡喃酮的高产率是通过简单的一锅通用程序实现的。
• Substituted pyrano[4,3-c]pyrazoles, compositions containing same, and
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04178379A1

  公开（公告）日：1979-12-11

  2,4,6,7-Tetrahydropyrano[4,3-c]pyrazoles are provided having the formula ##STR1## wherein Z is O, S, SO or SO.sub.2 ; R is H, halo, lower alkyl, lower alkoxy, lower alkanoyl, aroyl, cyano or CF.sub.3 ; and R' is H, lower alkyl, aryl-lower alkyl, aryl or halo-lower alkyl. In addition, pharmaceutical compositions containing the above compounds and a method of using same to treat inflammatory conditions in mammalian species is also provided.

  本发明提供了具有以下公式的2,4,6,7-四氢吡喃并[4,3-c]吡唑：##STR1## 其中Z为O，S，SO或SO.sub.2; R为H，卤素，低烷基，低烷氧基，低烷酰基，芳酰基，氰基或CF.sub.3; R'为H，低烷基，芳基-低烷基，芳基或卤素-低烷基。此外，本发明还提供了含有上述化合物的制药组合物以及使用它们来治疗哺乳动物物种中的炎症状况的方法。
• Quinine-catalyzed enantioselective tandem conjugate addition/intramolecular cyclization of malononitrile and 1,4-dien-3-ones
  作者：Zhi-Peng Hu、Jian Li、Xiao-Gang Yin、Xue-Jing Zhang、Ming Yan

  DOI：10.3998/ark.5550190.0014.301

  日期：——

  An organocatalytic tandem conjugate addition / intramolecular cyclization of malononitrile and conformationally restricted 1,4-dien-3-ones has been developed. A series of cinchona alkaloids and their derivatives were examined as the catalysts. Quinine was found to be the most efficient catalyst in the absence of any additive. The reaction gave 2-amino-4H-pyrans with high yield and excellent enantiopurity

  已开发出丙二腈和构象受限的 1,4-二烯-3-酮的有机催化串联共轭加成/分子内环化。研究了一系列金鸡纳生物碱及其衍生物作为催化剂。在没有任何添加剂的情况下，奎宁被发现是最有效的催化剂。该反应仅使用 5 mol% 奎宁作为催化剂，以高收率和优异的对映纯度得到 2-氨基-4H-吡喃。
• Three-Component [3 + 3] Heterocyclizations for Flexible Synthesis of Bicyclic Fused Pyridines Under Microwave Irradiation
  作者：Jie Liu、Yuan-Yuan Pan、Li-Yuan Xue、Wen-Juan Hao、Jin-Peng Zhang、Shu-Liang Wang、Bo Jiang

  DOI：10.1002/jhet.2438

  日期：2016.7

  Three‐component [3 + 3] heterocyclizations have been established under microwave irradiation, providing a flexible synthetic approach toward bicyclic fused pyridines. 3,5‐Dibenzylidenedihydro‐2H‐pyran‐4(3H)‐ones were subject with malononitrile and aromatic amines in cosolvent of HOAc and N,N‐dimethylformamide, affording 10 examples of pyrano[4,3‐b]pyridine derivatives in good to excellent yields. Similarly

  在微波辐射下已经建立了三组分[3 + 3]杂环，为双环稠合吡啶提供了灵活的合成方法。3,5-二苄基二氢-2 H-吡喃-4（3 H）-酮与丙二腈和芳香胺在HOAc和N，N-二甲基甲酰胺的共溶剂中共存，提供了10个吡喃并[4,3- b ]吡啶衍生物实例高产到高产。同样，使用硫拴系杂环作为反应伙伴，获得了七个硫吡喃并[4,3- b ]吡啶衍生物的实例。