4-methyl-6-phenyl-5,6-dihydro-2H-pyran-2-one | 29643-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-methyl-6-phenyl-5,6-dihydro-2H-pyran-2-one
• 英文别名: 5,6-dihydro-4-methyl-6-phenyl-2H-pyran-2-one；4-methyl-6-phenyl-5,6-dihydropyran-2-one；3-methyl-5-phenyl-2-penten-5-olide；4-methyl-6-phenyl-5,6-dihydro-pyran-2-one；4-Methyl-6-phenyl-5,6-dihydro-pyran-2-on；4-methyl-2-phenyl-2,3-dihydropyran-6-one
• CAS: 29643-79-6
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: SVMFLXHTBXCJEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  130 °C(Press: 0.1 Torr)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-methyl-6-phenyl-5,6-dihydro-2H-pyran-2-one 在 三乙基硅烷 、 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 3,6-二氢-4-甲基-2-苯基-2H-吡喃
  参考文献：
  名称：

  Conversion of lactones into ethers

  摘要：

  DOI：

  10.1021/jo00324a050
• 作为产物：
  描述：

  2-[(E)-4-phenylbut-3-en-2-ylidene]propanedioic acid 在 哌啶 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 4-methyl-6-phenyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  A survey of mono- or bis-decarboxylation of β-methyl polyethylenic-malonic acids

  摘要：

  Diverse experimental conditions, leading to mono- or bis-decarboxylation of beta-methyl polyethylenic-malonic acids, were examined. A clean and easy bis-decarboxylation was reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01022-0

文献信息

• GENERAL METHOD FOR INCREASING STEREOSELECTIVITY IN STEREOSELECTIVE REACTIONS
  申请人：Meyer Matthew P.

  公开号：US20090163741A1

  公开（公告）日：2009-06-25

  This invention is directed to a method of performing a stereoselective reaction without use of a solvent comprising contacting a reactant with a chiral reagent under sonication conditions to form an excess of an enantiomer.

  这项发明涉及一种在无溶剂的情况下执行立体选择反应的方法，包括将反应物与手性试剂在声波条件下接触，形成一种对映体的过量。
• Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation(allylation)-ring closing metathesis–oxidation sequence
  作者：J.Alberto Marco、Miguel Carda、Santiago Rodrı́guez、Encarnación Castillo、Marı́a N. Kneeteman

  DOI：10.1016/s0040-4020(03)00584-2

  日期：2003.6

  aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl or homoallyl ethers, respectively. Ring-closing metathesis of these compounds afforded in many cases cyclic ethers (dihydrofurans and dihydropyrans, respectively) bearing disubstituted and trisubstituted CC bonds. These were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones. Reasons

  醛和酮的亲核C-乙烯基化和C-烯丙基化，然后将得到的甲醇进行O-烯丙基化，分别得到相应的烯丙基或高烯丙基醚。这些化合物的闭环易位在许多情况下提供带有二取代和三取代的CC键的环状醚（分别为二氢呋喃和二氢吡喃）。然后将它们进行烯丙基氧化以产生共轭的γ-和δ-内酯。介绍并讨论了观察到的故障的原因。
• Synthesis of Conjugated γ- and δ-Lactones from Aldehydes and Ketones via a Vinylation/Allylation-Ring Closing Metathesis-Oxidation Sequence
  作者：Miguel Carda、Encarnación Castillo、Santiago Rodríguez、Santiago Uriel、J. Alberto Marco

  DOI：10.1055/s-1999-2897

  日期：——

  Nucleophilic C-vinylation or C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl ethers. Ring-closing metathesis of the latter afforded cyclic ethers (dihydrofurans and dihydropyrans, respectively) which were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones.

  通过对醛和酮进行亲核碳乙烯基化或碳烯丙基化反应，随后对所得卡宾醇进行氧烯丙基化，得到了相应的烯丙醚。后者经过环闭合易位反应，分别得到环醚（二氢呋喃和二氢吡喃），再经过烯丙位的氧化反应，分别生成共轭的γ-和δ-内酯。
• [3 + n] Annulation Reactions by Means of 3-Trimethylstannyl-2-[(trimethylstannyl)methyl]propene, an Isobutene Dianion Synthetic Equivalent
  作者：Alessandro Degl'Innocenti、Pasquale Dembech、Alessandro Mordini、Alfredo Ricci、Giancarlo Seconi

  DOI：10.1055/s-1991-26441

  日期：——

  Stepwise functionalization of the two carbon-tin bonds in 3-trimethylstannyl-2-[(trimethylstannyl)methyl]propene with electrophiles (diacyl dichlorides or aldehydes and carbon dioxide, provides a promising route for [3 + n] annulation reactions.

  3- 三甲基锡-2-[(三甲基锡)甲基]丙烯中的两个碳-锡键与亲电体（二酰二氯或醛和二氧化碳）的逐步官能化为 [3 + n] 环化反应提供了一条很有前景的途径。
• Three-step assembly of 4-aminotetrahydropyran-2-ones from isoxazoline-2-oxides
  作者：A. S. Naumova、A. A. Mikhaylov、Yu. A. Khomutova、R. A. Novikov、D. E. Arkhipov、A. A. Korlyukov、S. L. Ioffe

  DOI：10.1039/c3ra47309k

  日期：——

  constructed by a three step protocol from easily available isoxazoline 2-oxides. In the first stage, the carbon skeleton of the target product is formed upon a C,C-coupling of a silyl ketene acetal with a nitronate function, under silyl triflate catalysis. The key step of the assembly consists of the oxidative cleavage of an endocyclic N–O bond of intermediate cyclic nitroso acetals with mCPBA, accompanied

  具有3-氨基官能团的四氢吡喃-2-酮与叔碳原子连接（一种广泛存在的天然片段），是通过三步操作从易得的异恶唑啉2氧化物中合成的。在第一阶段中，目标产物的碳骨架是在三氟甲磺酸硅烷基酯催化下，将具有亚硝酸盐官能团的甲硅烷基乙烯酮缩醛进行C，C偶联而形成的。组装的关键步骤包括中间环亚硝基缩醛与m CPBA的内环N-O键的内环N-O键的氧化裂解，伴随着内酯环的闭合，产生β-硝基-δ-内酯的产率为63-85％。 。后者用合并的铝还原，以提供目标支架。