2-vinyl-γ-butyrolactone | 43142-60-5

• 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: 2-vinyl-γ-butyrolactone
• 英文别名: 3-Ethylidene-4,5-dihydro-2(3H)-furanone；α-vinyl-γ-butyrolactone；3-Vinyl-4,5-dihydro-2(3H)-furanon；3-vinyl-dihydro-furan-2-one；vinylbutyrolactone；3-ethenyloxolan-2-one
• CAS: 43142-60-5
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: IOTNLSAKNNGZGC-UHFFFAOYSA-N

物化性质

• 沸点：
  41-42 °C(Press: 0.5 Torr)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  1
• 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：

  2-vinyl-γ-butyrolactone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 生成 3-ethylidenedihydro-2(3H)-furanone
  参考文献：
  名称：

  Efficient Synthesis of 2-Vinyl-γ-butyrolactones and 2-Vinyl-γ-butyrolactams by Palladium-Catalyzed Decarboxylative Carbonylation

  摘要：

  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。

  DOI：

  10.1246/bcsj.65.97
• 作为产物：
  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

文献信息

• Stereochemical consequence in the elimination of β-hydroxyalkylsilanes: Stereoselective formation of (Z)- and (E)-alkylidene-γ-butyrolactones
  作者：Keiji Yamomoto、Yoichi Tomo、Shigeaki Suzuki

  DOI：10.1016/s0040-4039(00)78628-x

  日期：1980.1

  Titanium(IV) chloride-mediated reaction of 4,5-dihydro-2-(trimethylsiloxy)-3-(trimethylsilyl)furan (1a) with acetaldehyde gave diastereomerically pure (3S*, 1′R*)-4,5-dihydro-3-(1′hydroxyethyl)-3-(trimethylsilyl)-2(3H)furanone (2a), which afforded selectively either (Z)- or (E)-α-ethylidene-γ-butyrolactone (3a) under proper conditions. Facile isomerization of 2a into diastereomerically pure (3S*, 1′R*)-4

  钛（IV），氯化介导的4,5-二氢-2-（三甲基硅氧基）-3-（三甲基硅烷基）呋喃（1a）的反应与乙醛，得到对映异构纯（3小号*，1' - [R *）-4,5-二氢-3-（1'羟乙基）-3-（三甲基甲硅烷基）-2（3H）呋喃酮（2a），在适当的条件下有选择地提供（Z）-或（E）-α-亚乙基-γ-丁内酯（3a）情况。2a的容易异构化为非对映体纯的（3小号*，1' - [R *）-4,5-二氢-3 - ＆1' - （三甲基硅氧基）乙基} -2-（3H）呋喃酮（4）表明一个有趣的立体化学结果从2a到（E）-3a通过4的烯醇化。
• Preparation of tetrahydropyran-4-carboxylic acid and esters thereof
  申请人：BASF Aktiengesellschaft

  公开号：US05371246A1

  公开（公告）日：1994-12-06

  A process for the preparation of tetrahydropyran-4-carboxylic acid and esters thereof of the general formula I ##STR1## in which R.sup.1 denotes hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.8 cycloalkyl, or aryl by the reaction of a dihydro-2(3H)furanone of the general formula II ##STR2## in which R.sup.2 denotes hydrogen, C.sub.1 -C.sub.6 alkyl, or --CO--R.sup.3 and R.sup.3 denotes hydrogen or C.sub.1 -C.sub.6 alkyl, with water or an alcohol of the general formula III R.sup.1 --OH (III), in which R.sup.1 has the aforementioned meaning, at temperatures ranging from 200.degree. to 350.degree. C. in the presence of a heterogenous acid catalyst, in which use is made of a fixed heterogenous acid catalyst.

  一种制备一般式I的四氢吡喃-4-羧酸及其酯的方法，其中R1表示氢、C1-C6烷基、C5-C8环烷基或芳基，通过将一般式II的二氢-2（3H）呋喃酮与水或一般式III R1-OH（III）的醇反应，其中R1具有上述含义，在200℃至350℃的温度下，在固定的异相酸催化剂的存在下进行。
• Use of quinolizine and quinolizinone derivatives in the manufacture of medicaments for increasing gastric motility
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0329905A1

  公开（公告）日：1989-08-30

  The present invention is directed to the use of esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-­ones and hexahydro-8-hydroxy-2,6-methano-2H-quinolizines in the manufacture of gastric motility stimulants.

  本发明涉及六氢-8-羟基-2,6-甲桥-2H-喹嗪-3(4H)-酮和六氢-8-羟基-2,6-甲桥-2H-喹嗪的酯类在胃动力兴奋剂生产中的应用。
• Use of quinolizine and quinolizinone derivatives in the manufacture of medicaments
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0329932A2

  公开（公告）日：1989-08-30

  The present invention relates to the use of quinolizine and quinolizinone derivatives in the manufacture of a medicament for the treatment of anxiety, psychosis, glaucoma, and to stimulate gastric motility. The invention also relates to certain novel derivatives of quinolizine and quinolizinone which are useful for the purposes indicated above and which are also useful for the treatment of migraine and the treatment of nausea and vomiting.

  本发明涉及使用喹嗪和喹嗪酮衍生物制造治疗焦虑症、精神病、青光眼和刺激胃肠蠕动的药物。本发明还涉及喹嗪和喹嗪酮的某些新型衍生物，这些衍生物可用于上述目的，也可用于治疗偏头痛和治疗恶心呕吐。
• Use of quinolizine and quinolizinone derivatives in the manufacture of medicaments for the treatment of cardiac arrhythmias
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0330824A1

  公开（公告）日：1989-09-06

  The present invention is directed to the use of hetrocyclic esters of hexahydro-8-hydroxy-2,6-methano-2H-­quinolizin-3(4H)-one and hexahydro-8-hydroxy-2,6-methano-2H-­quinolizines as cardiac antiarrhythmic agents.

  本发明是关于六氢-8-羟基-2,6-甲桥-2H-喹嗪-3(4H)-酮和六氢-8-羟基-2,6-甲桥-2H-喹嗪的六环酯作为抗心律失常药物的用途。