2-丙基-2,6,7,8-四氢色烯-5-酮 | 234774-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-丙基-2,6,7,8-四氢色烯-5-酮
• 英文名称: 2-Propyl-2,6,7,8-tetrahydro-chromen-5-one
• 英文别名: 2-propyl-2,6,7,8-tetrahydrochromen-5-one
• CAS: 234774-56-2
• 化学式: C₁₂H₁₆O₂
• mdl: MFCD08752445
• 分子量: 192.258
• InChiKey: XAHMZLCWLWMPGH-UHFFFAOYSA-N

物化性质

• 沸点：
  333.9±22.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.583
• 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：

  丁炔二酸二甲酯 、 2-丙基-2,6,7,8-四氢色烯-5-酮 以 甲苯 为溶剂， 反应 24.0h， 以41%的产率得到5-Oxo-5,6,7,8-tetrahydronaphthalin-1,2-dicarbonsaeure-dimethylester
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo020688t
• 作为产物：
  描述：

  2-已烯醛 、 1,3-环己二酮 在 哌啶 、 乙酸酐 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 37.08h， 以55%的产率得到2-丙基-2,6,7,8-四氢色烯-5-酮
  参考文献：
  名称：

  Formal Cycloaddition Reactions of Vinylogous Amides with α,β-Unsaturated Iminiums. A Strategy for Constructing Piperidinyl Heterocycles

  摘要：

  A formal [3 + 3] cycloaddition strategy for constructing piperidinyl heterocycles from vinylogous amides and alpha,beta-unsaturated iminiums is described here, These reactions proceed well, leading to various heterocycles that could serve as useful synthetic building blocks. Comparative studies between the reactivities of vinylogous amides and other 1,3-diketo systems have also been examined. Preferences for the nitrogen atom during the electrocyclic ring closure step are noted in these reactions, and preliminary calculations suggest that these preferences could result from electronic factors.

  DOI：

  10.1021/ol990107v

文献信息

• Lipase-catalyzed regioselective domino reaction for the synthesis of chromenone derivatives
  作者：Qi Yang、Long-Hua Zhou、Wan-Xia Wu、Wei Zhang、Na Wang、Xiao-Qi Yu

  DOI：10.1039/c5ra13267c

  日期：——

  An efficient synthesis of 2H-chromenones and 2-hydroxyl-2H-chromenones derivatives has been developed from 1,3-dicarbonyls and α,β-unsaturated aldehydes by a controllable regioselective domino cyclization reaction under catalysis of different lipases. 2H-Chromenones derivatives were synthesized by bovine pancreatic lipase (BPL) in acetonitrile, while lipase from Pseudomonas fluorescens (PFL) can catalyze

  为2个的有效的合成ħ -chromenones和2-羟基-2- ħ -chromenones衍生物已经从1,3-二羰基和α，β不饱和醛通过在不同脂肪酶催化的可控区域选择性多米诺环化反应的发展。2 H- Chromenones衍生物是由牛胰脂肪酶（BPL）在乙腈中合成的，而荧光假单胞菌（PFL）的脂肪酶则可以在二氯甲烷中以中等至高收率催化2-hydroxyl-2 H -chromenones衍生物的合成。
• 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.