3-甲基-6,7,8,9-四氢-5ah-吡喃并[4,3-b]色烯-1-酮 | 194796-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 3-甲基-6,7,8,9-四氢-5ah-吡喃并[4,3-b]色烯-1-酮
• 英文名称: 3-Methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran
• 英文别名: 3-Methyl-1H-5a,6,7,8,9-pentahydro-1-oxopyrano[4,3-b][1]benzopyran；3-Methyl-6,7,8,9-tetrahydro-5aH-pyrano[4,3-b]chromen-1-one
• CAS: 194796-93-5
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: OOEUMXVXNXRROJ-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  408.5±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 、 1-cyclohexene-1-carboxaldehyde 在 2,4,8,10-tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 以99%的产率得到3-甲基-6,7,8,9-四氢-5ah-吡喃并[4,3-b]色烯-1-酮
  参考文献：
  名称：

  布朗斯台德酸通过正式的[3 + 3]环加成反应合成吡喃

  摘要：

  布朗斯台德酸通过正规的[3 + 3]环加成反应，在温和的条件下以高收率催化将可烯化的β-酮酯加成到α，β-不饱和醛上，从而以高收率生成取代的2H-吡喃。

  DOI：

  10.1002/adsc.200700375

文献信息

• Brønsted Acid‐Catalyzed Synthesis of Pyrans <i>via</i> a Formal [3+3] Cycloaddition
  作者：Claudie Hubert、Julie Moreau、Jessika Batany、Agathe Duboc、Jean‐Pierre Hurvois、Jean‐Luc Renaud

  DOI：10.1002/adsc.200700375

  日期：2008.1.4

  Brønsted acids catalyze the addition of enolizable β-keto esters to α,β-unsaturated aldehydes leading to substituted 2H-pyrans in good yields under mild conditions via a formal [3+3] cycloaddition.

  布朗斯台德酸通过正规的[3 + 3]环加成反应，在温和的条件下以高收率催化将可烯化的β-酮酯加成到α，β-不饱和醛上，从而以高收率生成取代的2H-吡喃。
• A Lewis Acid-Catalyzed Formal [3 + 3] Cycloaddition of α,β-Unsaturated Aldehydes with 4-Hydroxy-2-Pyrone, Diketones, and Vinylogous Esters
  作者：Aleksey V. Kurdyumov、Nan Lin、Richard P. Hsung、Glen C. Gullickson、Kevin P. Cole、Nadiya Sydorenko、Jacob J. Swidorski

  DOI：10.1021/ol0523042

  日期：2006.1.1

  A Lewis acid-catalyzed formal cycloaddition of alpha,beta-unsaturated aldehydes with 6-methyl-4-hydroxy-2-pyrone, 1,3-diketones, and vinylogous silyl esters is described here.
• A Formal [3 + 3] Cycloaddition Reaction. Improved Reactivity Using α,β-Unsaturated Iminium Salts and Evidence for Reversibility of 6π-Electron Electrocyclic Ring Closure of 1-Oxatrienes
  作者：Hong C. Shen、Jiashi Wang、Kevin P. Cole、Michael J. McLaughlin、Christopher D. Morgan、Christopher J. Douglas、Richard P. Hsung、Heather A. Coverdale、Aleksey I. Gerasyuto、Juliet M. Hahn、Jia Liu、Heather M. Sklenicka、Lin-Li Wei、Luke R. Zehnder、Craig A. Zificsak

  DOI：10.1021/jo020688t

  日期：2003.3.1

  A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. The usage of alpha,beta-unsaturated iminium salts is significant in controlling competing reaction pathways to give exclusively 2H-pyrans. Most significantly, experimental evidence is provided to support the mechanism of this reaction that involves a sequential Knoevenagel condensation and a reversible 6pi-electron electrocyclic ringclosure of 1-oxatrienes.
• A One-Pot Condensation of Pyrones and Enals. Synthesis of 1<i>H</i>,7<i>H</i>-5a,6,8,9-Tetrahydro-1-oxopyrano[4,3-<i>b</i>][1]benzopyrans
  作者：Duy H. Hua、Yi Chen、Hong-Sig Sin、Maria J. Maroto、Paul D. Robinson、Steven W. Newell、Elisabeth M. Perchellet、James B. Ladesich、Jonathan A. Freeman、Jean-Pierre Perchellet、Peter K. Chiang

  DOI：10.1021/jo970642d

  日期：1997.10.1

  Condensation of various 6-substituted 4-hydroxypyrones 1 with 1-cyclohexenecarboxaldehydes in the presence of L-proline in ethyl acetate gave high yields of substituted 1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyrans. The reaction presumably occurs via the 1,2-addition of the pyrone with the aldehyde followed by dehydration and then cyclization through a 6 Pi electrocyclic process. A remarkable asymmetric induction was obtained from a stereogenic center (C4) of the cyclohexenecarboxaldehyde [such as (S)-perillaldehyde] to provide only the C5a,7-trans tricyclic pyrone products. On the other hand, condensation of S-(formyloxy)- or 3-hydroxy-2-methyl-1-cyclohexene-carboxaldehydes with pyrones 1 gave mixtures of C5a,6-cis and -trans products. Several of the tricyclic pyrones strongly inhibit acetylcholinesterase activity, DNA synthesis, and tumor cell growth in vitro.
• US5958970A
  申请人：——

  公开号：US5958970A

  公开（公告）日：1999-09-28