3-ethylidenedihydro-2(3H)-furanone | 43142-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-ethylidenedihydro-2(3H)-furanone
• 英文别名: (E)-α-ethylidene-γ-butyrolactone；(E)-3-ethylidenetetrahydrofuran-2-one；3-trans-ethylidene-tetrahydro-2-furanone；(3E)-3-ethylidenedihydrofuran-2(3H)-one；(3E)-3-ethylideneoxolan-2-one
• CAS: 43142-58-1
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: IDXLALZVWZGIDG-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-ethylidenedihydro-2(3H)-furanone 以 甲醇 为溶剂， 反应 6.5h， 以75%的产率得到2-vinyl-γ-butyrolactone
  参考文献：
  名称：

  A Convenient Synthesis of α-Vinyl-lactones by Photo-Deconjugation of α,β-Unsaturated γ- or δ-Lactones

  摘要：

  DOI：

  10.1055/s-1983-30609
• 作为产物：
  描述：

  (3RS,1'SR)-4,5-dihydro-3-(1'-hydroxy-ethyl)-3-(phenylthio)furan-2(3H)-one 在 2-fluoro-1-ethylpyridinium tetrafluoroborate 、 三乙胺 、 lithium iodide 作用下， 生成 3-ethylidenedihydro-2(3H)-furanone
  参考文献：
  名称：

  Preparation of .beta.-hydroxy-.alpha.-phenylthio esters via condensation of aldehydes with .alpha.-phenylthioester enolate anions

  摘要：

  DOI：

  10.1021/jo01306a002

文献信息

• A new stereospecific route to α-alkylidene γ-lactones
  作者：W. Roy Jackson、Patrick Perlmutter、Andrew J. Smallridge

  DOI：10.1039/c39850001509

  日期：——

  Hydrocyanation of a range of protected β-hydroxyalkynes give unsaturated nitriles which can be cyclised to α-alkylidene γ-lactones and in most cases the regioselectivity of hydrocyanation can be controlled giving the desired cyanoalkenes with stereospecific formation of the E-isomer.

  一系列受保护的β-羟基炔烃的氢氰化产生不饱和腈，其可以环化为α-亚烷基γ-内酯，并且在大多数情况下，可以控制氢氰化的区域选择性，从而得到具有立体异构的E-异构体的所需氰基烯烃。
• The clerodane ring system: investigating the viability of a direct Diels–Alder approach
  作者：Andrew T. Merritt、Rebecca H. Pouwer、David J. Williams、Craig M. Williams、Steven V. Ley

  DOI：10.1039/c1ob05422h

  日期：——

  A direct synthetic approach to the spiro-γ-lactone clerodane ring system has been investigated. This work builds on that of Jung and highlights the inherent difficulties associated with the otherwise obvious Diels–Alder approach.

  研究了螺-γ-内酯环戊烷环系统的直接合成方法。这项工作以荣格（Jung）的工作为基础，强调了与其他明显的Diels-Alder方法有关的固有困难。
• Asymmetric hydrogenation of unsaturated carbonyl compounds catalyzed by BINAP-Ru(II) complexes. Enantioselective synthesis of γ-butyrolactones and cyclopentanones
  作者：Tetsuo Ohta、Tsutomu Miyake、Nobuo Seido、Hidenori Kumobayashi、Susumu Akutagawa、Hidemasa Takaya

  DOI：10.1016/s0040-4039(00)92330-x

  日期：1992.1

  Asymmetric hydrogenation of 2- and 4-alkylidene-γ-butyrolactones and 2-alkylidenecyclopentanones catalyzed by BINAP—Ru(II) complexes affords the corresponding γ-butyrolactones and cyclopentanones in 94–98% ee. Hydrogenation of (E)- and (Z)-2-propylidene-γ-butyrolactone catalyzed by the same catalyst gave the products with the same absolute configuration and in almost equal enantioselectivities, which

  BINAP-Ru（II）配合物催化2-和4-亚烷基-γ-丁内酯和2-亚烷基环戊酮的不对称加氢，可得到94-98％ee的相应γ-丁内酯和环戊酮。在同一催化剂下催化的（E）-和（Z）-2-亚丙基-γ-丁内酯的加氢反应得到的产物具有相同的绝对构型和几乎相等的对映选择性，这表明烯烃的几何形状不会影响立体化学和对映选择性。
• Stereospecific nuclephilic addition reaction of thiophenol to .ALPHA.,.BETA.-unsaturated esters.
  作者：Okiko MIYATA、Tetsuro SHINADA、Takeaki NAITO、Ichiya NINOMIYA

  DOI：10.1248/cpb.37.3158

  日期：——

  A concerted method for the stereospecific addition of thiophenol to α, β-unsaturated esters 1 and 3 has been developed. This provides a convenient route for the stereo-selective preparation of less available Z__--α, β-unsaturated esters and lactones 3.

  我们开发了一种将噻吩酚与α、β-不饱和酯 1 和 3 进行立体特异性加成的协同方法。这为立体选择性制备较少的 Z__--α、β--不饱和酯和内酯 3 提供了一条便捷的途径。
• Efficient Synthesis of 2-Vinyl-γ-butyrolactones and 2-Vinyl-γ-butyrolactams by Palladium-Catalyzed Decarboxylative Carbonylation
  作者：Takashi Bando、Shuji Tanaka、Keigo Fugami、Zen-ichi Yoshida、Yoshinao Tamaru

  DOI：10.1246/bcsj.65.97

  日期：1992.1

  4-Vinyl-1,3-dioxan-2-ones (cyclic carbonates) undergo decarboxylation-carbonylation by the catalysis of Pd(0) species under CO (in most cases, 1 atm) to provide 2-vinyl-γ-butyrolactones in good yields. The course of the reaction of 6-vinyltetrahydro-2H-1,3-oxazin-2-ones (cyclic carbamates) depends on the substituent on the nitrogen atom. When it is H or Ts (and COPh), 2-vinyl-γ-butyrolactams or 6-amino-3-hexenoic acid esters are obtained. Cyclic N-benzylcarbamates are unreactive. trans-2,3-Disubstituted lactones and lactams arise stereoselectively from carbonates and carbamates, irrespective of their stereochemistry, respectively.

  4-乙烯基-1,3-二恶烷-2-酮（环状碳酸酯）在 CO（大多数情况下为 1 个大气压）下，通过 Pd(0) 物质的催化作用进行脱羧-羰基化，生成 2-乙烯基-γ-丁内酯良好的产量。 6-乙烯基四氢-2H-1,3-恶嗪-2-酮（环状氨基甲酸酯）的反应过程取决于氮原子上的取代基。当它是H或Ts(和COPh)时，获得2-乙烯基-γ-丁内酰胺或6-氨基-3-己烯酸酯。环状N-苄基氨基甲酸酯不具有反应性。反式2,3-二取代内酯和内酰胺分别立体选择性地由碳酸酯和氨基甲酸酯产生，无论其立体化学如何。

表征谱图