2-甲基-2-(3-戊炔-1-基)-1,3-二氧戊环 | 22592-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-2-(3-戊炔-1-基)-1,3-二氧戊环
• 英文名称: 2-(ethylenedioxy)-5-heptyne
• 英文别名: 5-heptyn-2-one ethylene ketal；2-Methyl-2--<1,3>-dioxolan；2-methyl-2-pent-3-ynyl-[1,3]dioxolane；2-Methyl-2-pent-3-ynyl-1,3-dioxolane
• CAS: 22592-16-1
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: VLIFFBAMCXCKEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-2-(3-戊炔-1-基)-1,3-二氧戊环 在 lithium aluminium tetrahydride 、 乙醇 、 硫酸 、 锌 作用下， 以 丙酮 、 苯 为溶剂， 生成 3-methyl-2-octen-6-yn-1-ol
  参考文献：
  名称：

  Direct conversion of terpenylalkanolamines to ethylidyne N-nitroso compounds

  摘要：

  DOI：

  10.1021/jo00364a013
• 作为产物：
  描述：

  5-己炔-2-酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 19.0h， 生成 2-甲基-2-(3-戊炔-1-基)-1,3-二氧戊环
  参考文献：
  名称：

  分子内环加成法合成（±）-肌act啶

  摘要：

  描述了一种新的（±）-act啶（1）合成，该合成依赖于乙炔在嘧啶环上的分子内环加成。制备5-（庚基-5-yn-2-基）-4，6-二羟基嘧啶（2），然后热解，得到1-羟基act啶（13），可以通过氯化和氢化将其转化为（±）-act啶。

  DOI：

  10.1039/p19810001909

文献信息

• Synthesis of ketols of the natural pyrethrins
  作者：L. Crombie、P. Hemesley、Gerald Pattenden

  DOI：10.1039/j39690001016

  日期：——

  A stereospecific five-stage synthesis of (±)-cis-pyrethrolone is described, involving cis-octa-1,3-dien-7-one as the key intermediate. The ethylene acetal of this ketone was made by a Wittig reaction, under salt-free condiditions, with vaporised acraldehyde. The overall yield for the synthesis was 21%, and it provides highly pure (pm;)-cis-pyrethrolone for the first time. The material is spectrally

  描述了（±）-顺式-吡咯烷酮的立体有择的五阶段合成，涉及顺式-octa-1,3-dien-7-one作为关键中间体。该酮的乙缩醛是通过Wittig反应在无盐条件下与汽化的丙烯醛反应制得的。合成的总产率为21％，并且它首次提供了高纯度的（pm；）-顺式-吡咯烷酮。该物质与自然（+）-吡咯烷酮样品在光谱上相同。
• Ring-Enlarging Annulations. A One-Step Conversion of Cyclic Silyl Acyloins and .omega.-Alkynyl Acetals to Polycyclic Enediones
  作者：Aaron Balog、Dennis P. Curran

  DOI：10.1021/jo00107a011

  日期：1995.1

  new sequence of cationic reactions that converts cyclic silyl acyloins and omega-alkynyl acetals to polycyclic enediones is reported. For example, treatment of bis-1,2-((trimethylsilyl)oxy)cyclobutene and 2-(ethylenedioxy)-5-heptyne with excess boron trifluoride etherate in methylene chloride for 2 days provides 4-acetyl-3,5,6,6a-tetrahydro-6a-methyl-1-(2H)-pentalenone in 58% yield. This product is formed via a sequence involving a Mukaiyama aldol reaction, a pinacol ring expansion, and a 5-exo-dig alkynyl ketone cyclization. In the case of terminal alkynes, the last cyclization occurs in a 6-endo-dig fashion. The scope and limitations of this process are studied, and a number of bi- and tricyclic ring systems are formed.
• Implication of a common trimethylenemethane intermediate in dimer formation and structural methylenecyclopropane rearrangement of a bicyclo[3.1.0]hex-1-ene to a 5-alkylidenebicyclo[2.1.0]pentane
  作者：Richard F. Salinaro、Jerome A. Berson

  DOI：10.1021/ja00372a020

  日期：1982.4
• Annulative ring expansions. Direct conversion of .omega.-alkynyl acetals to polycyclic unsaturated ketones
  作者：Joseph Sisko、Aaron Balog、Dennis P. Curran

  DOI：10.1021/jo00042a007

  日期：1992.7

  Geminal acylation of omega-acetylenic acetals and bis(silyloxy)cycloalkenes under Lewis acid conditions preceded cationic cyclization of the alkyne onto the ketone to produce polycyclic unsaturated ketones.
• Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones
  作者：Aaron Balog、Steven V. Geib、Dennis P. Curran

  DOI：10.1021/jo00107a012

  日期：1995.1

  The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.