4-vinyltetrahydro-2H-pyran-2-one | 89030-33-1

• 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: 4-vinyltetrahydro-2H-pyran-2-one
• 英文别名: 4-vinyltetrahydropyran-2-one；4-ethenyl-tetrahydro-2H-pyran-2-one；2H-Pyran-2-one, 4-ethenyltetrahydro-；4-ethenyloxan-2-one
• CAS: 89030-33-1
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: DPTJFTFDPACGGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  227.7±29.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  4-vinyltetrahydro-2H-pyran-2-one 在 palladium on activated charcoal palladium diacetate 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 125.0 ℃ 、310.27 kPa 条件下， 反应 59.5h， 生成 Methyl 5-(2-methylsulfonyloxyethyl)-7-pyridin-3-ylheptanoate
  参考文献：
  名称：

  Thromboxane receptor antagonism combined with thromboxane synthase inhibition. 3. Pyridinylalkyl-substituted 8-[(arylsulfonyl)amino]octanoic acids

  摘要：

  A series of 8-[(arylsulfonyl)amino]octanoic acids substituted with a pyridinylalkyl group along the chain were synthesized and tested in vitro for their ability to both antagonize the binding of thromboxane A2 to its receptors and to inhibit the thromboxane synthase enzyme. This series of compounds were found to inhibit the U 46619-induced aggregation of human platelets and the U 46619-induced contraction of dog saphenous vein. The compounds also inhibited TxA2 biosynthesis in a human microsomal platelet preparation. The relative position of the pyridinylalkyl and arylsulfonamido groups had significant effects on the thromboxane receptor antagonist (TxRA) activity and thromboxane synthase inhibitor (TxSI) activity. Compounds with the pyridine ring at the 7- or 8-position of the octanoic acid side chain were weakly active as TxSI but behaved as potent TxRA at the platelet receptor for TxA2. However, these compounds were agonists at the vascular receptor. Substitution of the pyridinylalkyl group at the 2- or 3-position resulted in compounds with potent TxSI activity and weak TxRA activity. The activity profile of the compounds with the pyridinylalkyl substitution at the 4-, 5-, or 6-position was very desirable. Compound 22 with a pyridinylpropyl substituent at the 4-position was found to display extremely potent TxRA and TxSI properties.

  DOI：

  10.1021/jm00101a014
• 作为产物：
  描述：

  delta-戊内酯 在 W-4 Raney-Ni copper(l) iodide 、 正丁基锂 、 二异丙胺 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 22.67h， 生成 4-vinyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  一种有用的 3-取代 δ-内酯合成方法。(±)-Secocrispiolide的合成

  摘要：

  2-Phenylthio-2-penten-5-olide (1) 作为反应性迈克尔受体对一些典型的碳亲核试剂产生 3-取代的 2-phenylthio-5-pentanolides (2)，它们都可以转化为 3-取代的 5-通过还原脱硫生成戊醇内酯，并通过次磺酸同步消除衍生自 2 的亚砜 4 生成 3-取代的 2-戊烯-5-内酯。4 的普默勒重排提供 3-取代的 2-苯硫基-2-戊烯-5-内酯和/或2-羟基-2-戊烯-5-内酯。(±)-Secocrispiolide 是通过 1 与格氏试剂的迈克尔反应获得的加合物合成的，该试剂由 2,6-二甲基苄基溴和镁制备。

  DOI：

  10.1246/bcsj.64.1479

文献信息

• (Arylsulfonamido- and pyridyl-)-substituted carboxylic acids and
  申请人：Ciba-Geigy Corporation

  公开号：US05025025A1

  公开（公告）日：1991-06-18

  Disclosed are the compounds of formula ##STR1## wherein A represents lower alkylene; B represents oxygen, sulfur, lower alkylene, lower alkylene interrupted by oxygen, sulfur, sulfinyl or sulfonyl, (oxy-, sulfinyl-, sulfonyl- or thio)-lower alkylene, lower alkenylene, phenylene or a direct bond; M represents lower alkylene, lower alkylene interrupted by oxygen, sulfur, sulfinyl or sulfonyl, (oxy-, sulfinyl, sulfonyl- or thio)-lower alkylene, lower alkenylene or a direct bond; or one of A, B and M represents lower alkylidenylene and the other two independently represent lower alkylene; R represents hydrogen unless A, B or M represents lower alkylidenylene in which case R represents the second bond to the adjacent aklylidenylene unsaturated carbon atom; Het represents 1-imidazolyl, 3-pyridyl, or 1-imidazolyl or 3-pyridyl substituted by lower alkyl; Ar represents carbocyclic or heterocyclic aryl; pharmaceutically acceptable ester and amide derivatives thereof; the N-oxides of said compounds wherein Het represents optionally substituted pyridyl; the said compounds of formula I wherein COOH is replaced by 5-tetrazolyl; and the pharmaceutically acceptable salts; which are useful as thromboxane synthetase inhibitors and thromboxane receptor antagonists.

  揭示了以下式的化合物##STR1##其中A代表较低的烷基; B代表氧、硫、较低的烷基、被氧、硫、亚砜或磺酰中断的较低的烷基、(氧基、亚砜基、磺酰基或硫基)-较低的烷基、较低的烯基、苯基或直接键; M代表较低的烷基、被氧、硫、亚砜或磺酰中断的较低的烷基、(氧基、亚砜基、磺酰基或硫基)-较低的烷基、较低的烯基或直接键; 或者A、B和M中的一个代表较低的烷基亚烯基，另外两个独立地代表较低的烷基; R代表氢，除非A、B或M代表较低的烷基亚烯基，在这种情况下R代表相邻烷基亚烯基不饱和碳原子的第二键; Het代表1-咪唑基、3-吡啶基，或者被较低烷基取代的1-咪唑基或3-吡啶基; Ar代表碳环或杂环芳基; 其药学上可接受的酯和酰胺衍生物; 其中Het代表可选择取代的吡啶基的N-氧化物; 公式I中COOH被5-四唑基取代的所述化合物; 和药学上可接受的盐; 这些化合物可用作血栓素合酶抑制剂和血栓素受体拮抗剂。
• Certain (arylsulfonamido- and imidazolyl-)-substituted carboxylic acids
  申请人：Ciba-Geigy Corporation

  公开号：US05153214A1

  公开（公告）日：1992-10-06

  The present invention is concerned with compounds of formula I ##STR1## wherein A, B, M, R, Ar and Het are as defined in the specification, pharmaceutically acceptable ester and amide derivatives thereof; N-oxides thereof, tetrazole derivatives thereof, and salts thereof. These compounds have valuable pharmacological activities, especially as inhibitors of thromboxane synthetase and as receptor antagonists of thromboxane A.sub.2 and prostaglandin H.sub.2.

  本发明涉及以下式I的化合物 ##STR1## 其中A、B、M、R、Ar和Het如规范中所定义，其药学上可接受的酯和酰胺衍生物；其N-氧化物，四唑衍生物和盐。这些化合物具有有价值的药理活性，特别是作为血栓素合酶的抑制剂和血栓素A.sub.2和前列腺素H.sub.2的受体拮抗剂。
• 2- (PHENYLTHIO)-2-PENTEN-5-OLIDE, A NEW BUILDING BLOCK FOR THE SYNTHESIS OF 3-SUBSTITUTED δ-LACTONES
  作者：Michiharu Kato、Akihiko Ouchi、Akira Yoshikoshi

  DOI：10.1246/cl.1983.1511

  日期：1983.10.5

  2- (Phenylthio)-2-penten-5-olide, readily accessible from δ-valelolactone, showed high electrophilic reactivities toward some typical carbon nucleophiles to give 3-substituted 2-(phenylthio)pentanolides, which were convertible to a variety of 3-substituted pentan-5-olides and 2-penten-5-olides.

  2-(苯硫基)-2-penten-5-内酯，易从δ-valelolactone获得，对一些典型的碳亲核试剂表现出较高的电亲和性，可以生成3-取代的2-(苯硫基)五醇内酯，进一步转化为多种3-取代的戊烯-5-内酯和2-penten-5-内酯。
• A synthetic strategy to bridged 2,3,8-trioxabicyclo[3,3,1]nonane endoperoxides
  作者：Sandra Gemma、Sanil Kunjir、Margherita Brindisi、Ettore Novellino、Giuseppe Campiani、Stefania Butini

  DOI：10.1016/j.tetlet.2012.12.075

  日期：2013.3

  appropriate synthetic strategy for the preparation of endoperoxide-containing bridged bicyclic scaffolds. Through a TMSOTf-promoted dehydrative cyclization strategy we synthesized 2,3,8-trioxabicyclo[3,3,1]nonane endoperoxides. Alkyl substituents at C4 of the bicyclic scaffold could be readily introduced through exposure to Grignard reagents.

  作为我们开发新型抗疟疾工作的一部分，我们对拟定一种合适的合成策略以制备含内过氧化物的桥连双环支架感兴趣。通过TMSOTf促进脱水环化策略，我们合成了2,3,8-三氧杂双环[3,3,1]壬烷过氧化物。通过暴露于格氏试剂可容易地引入双环支架的C4处的烷基取代基。
• Folding strain stereocontrol in cyclohexane ring formation by means of an intramolecular ester enolate alkylation reaction
  作者：Takashi Tokoroyama、Hisashi Kusaka

  DOI：10.1139/v96-279

  日期：1996.12.1

  Diastereoselectivity in the cyclization of ethyl 7-bromo-2-methylheptanoates with an additional substituent at various positions in the chain, by LDA treatment, was investigated in connection with ...

  通过 LDA 处理，研究了 7-溴-2-甲基庚酸乙酯与链中不同位置的附加取代基环化的非对映选择性。