3-(1-methylethoxy)-4(phenylethynyl)cyclobut-3-ene-1,2-dione | 114094-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-methylethoxy)-4(phenylethynyl)cyclobut-3-ene-1,2-dione
• 英文别名: 3-Isopropoxy-4-(phenylethynyl)-3-cyclobutene-1,2-dione；3-(2-phenylethynyl)-4-propan-2-yloxycyclobut-3-ene-1,2-dione
• CAS: 114094-73-4
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: GKYGQJRZSDWMPF-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  364.1±52.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氟甲基膦酸二乙酯 、 3-(1-methylethoxy)-4(phenylethynyl)cyclobut-3-ene-1,2-dione 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以67%的产率得到diethyl difluoro(1-hydroxy-2-isopropoxy-4-oxo-3-(phenylethynyl)cyclobut-2-enyl)methylphosphonate
  参考文献：
  名称：

  Synthesis of γ-Difluoromethylated Tetronate Derivatives from Squarates Using Difluoromethylphosphonate

  摘要：

  DOI：

  10.3987/com-18-s(f)29
• 作为产物：
  描述：

  2,3-bis(1-methylethoxy)-4-hydroxy-4-(phenylethynyl)-cyclobut-2-en-1-one 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 以98%的产率得到3-(1-methylethoxy)-4(phenylethynyl)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Cyclobutenediones as precursors to quinones and cyclopentenones

  摘要：

  DOI：

  10.1016/s0040-4020(01)80131-9

文献信息

• Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect
  作者：Songsong Gao、Xiangdong Hu

  DOI：10.1039/c7cc03340k

  日期：——

  A Ni-catalyzed ring-opening of α-hydroxycyclobutenones is reported herein. A remarkable ligand effect was observed during transformations following the ring-opening. The employment of PPh3 leads to the formation of 2-furanones 2 through a migration of an alkoxyl group, and 2-furanones 3 were generated through a migration of hydrogen in the presence of Xantphos, affording a divergent approach to 2-furanones

  本文报道了Ni催化的α-羟基环丁烯酮的开环。开环后的转化过程中观察到了显着的配体效应。PPh3的使用通过烷氧基的迁移导致形成2-呋喃酮2，而在Xantphos的存在下通过氢的迁移生成了2-呋喃酮3，从而提供了一种具有多种功能的2-呋喃酮的发散方法。组。
• The Squarate Ester−Polyquinane Connection. An Analysis of the Capacity of Achiral Divinyl Adducts To Rearrange Spontaneously to Polycyclic Networks Housing Multiple Stereogenic Centers
  作者：Leo A. Paquette、Tina M. Morwick

  DOI：10.1021/ja963214i

  日期：1997.2.1

  The condensation of diisopropyl squarate and related cyclobutene-1,2-diones with 2 equiv of the same alkenyl anion or 1 equiv each of two different alkenyl anions can be a very effective method for the highly stenocontrolled synthesis of di-, tri-, and tetraquinanes. Two reaction cascades have been identified, The most prevalent and often exclusive reaction course is triggered by trans 1,2-addition of the two nucleophiles. Two consecutive conrotatory processes subsequently arise to deliver a doubly charged eight-membered ring intermediate, protonation of which leads to transannular adolization. The second option begins with cis 1,2-addition, this event triggering structural reorganization via a dianionic oxy-Cope rearrangement, When the alkenyl anions are sufficiently substituted, the two pathways are distinguishable on stereochemical grounds, A minor pathway consisting of trans 1,4-addition is seen to operate in certain contexts, especially when the alkenyllithium is ''soft''. Acetylide anions can also be utilized successfully; in such cases, the benefit of regiocontrolled protonation surfaces and gives rise to a single product, Other aspects of these complex tandem reactions have been investigated and are discussed.
• Synthesis of γ-Trifluoromethyl Tetronate Derivatives from Squarates
  作者：Yoshihiko Yamamoto、Yosuke Takamizu、Takashi Kurohara、Masatoshi Shibuya

  DOI：10.3987/com-16-s(s)12

  日期：——

  Squarates and semisquarates were treated with TMSCF3 in the presence of a catalytic amount of AcONa in DMF at room temperature to afford 4-trifluoromethyl-4-hydroxycyclobutenones. Subsequent oxidative ring expansion of these products was performed using Pb(OAc)(4) in the presence of MS 4A in 1,2-dichloroethane at 50 degrees C to afford gamma-trifluoromethyl tetronate derivatives.
• An improved method for the synthesis of substituted cyclobutenediones
  作者：Lanny S. Liebeskind、Richard W. Fengl、Kevin R. Wirtz、Thomas T. Shawe

  DOI：10.1021/jo00246a017

  日期：1988.5
• Rearrangement of 2-Dienylcyclobutenones. Synthesis of Highly Substituted Annulated Furans
  作者：Philip Turnbull、Matthew J. Heileman、Harold W. Moore

  DOI：10.1021/jo952247y

  日期：1996.1.1