5-ethynyl-γ-butyrolactone | 118800-14-9

• 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: 5-ethynyl-γ-butyrolactone
• 英文别名: 5-ethynyldihydrofuran-2(3H)-one；5-Ethynyloxolan-2-one
• CAS: 118800-14-9
• 化学式: C₆H₆O₂
• 分子量: 110.112
• InChiKey: UZFFBWUKQQYIQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：

  pentacarbonyl(1-methoxybenzylidene)chromium(0) 、 5-ethynyl-γ-butyrolactone 以 苯 为溶剂， 反应 14.0h， 以45%的产率得到(±)-5-(3-oxo-2,3-dihydro-1H-inden-1-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  带有碳酸盐或酰氧基基团的炔烃的费歇尔卡宾戊烯化反应：3-取代的1-茚满酮的合成。

  摘要：

  各种芳基菲舍尔卡宾烯与具有相邻酰氧基或碳酸酯基团的炔反应，以区域选择性地递送3-取代的1-茚满酮。酰氧基或碳酸酯基团可能与Cr金属配位，得到四配位的铬络合物，形成六元环，该环阻碍了烯键形成所需的CO插入乙烯酮。可选地，邻位芳基环的进攻导致戊环化，从而提供区域选择性的3-取代的1-茚满酮。该方法扩展到3-表位-异泛醇的核心结构的合成。

  DOI：

  10.1021/acs.orglett.0c00901
• 作为产物：
  描述：

  methyl 4-oxo-6-(trimethylsilyl)hex-5-ynoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 5-ethynyl-γ-butyrolactone
  参考文献：
  名称：

  Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide

  摘要：

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.

  DOI：

  10.1021/jm00124a022

文献信息

• [DE] VERFAHREN ZUR HERSTELLUNG VON 3-ARYL-PROPINEN UND NEUE 3-ARYL-PROPINE<br/>[EN] PROCESS FOR PRODUCING 3-ARYL PROPINES AND NOVEL 3-ARYL PROPINES<br/>[FR] PROCEDE DE PRODUCTION DE 3-ARYLPROPINES
  申请人：BAYER AKTIENGESELLSCHAFT

  公开号：WO1995021144A1

  公开（公告）日：1995-08-10

  (DE) Die Erfindung betrifft ein Verfahren zur Herstellung von 3-Aryl-propinen, dadurch gekennzeichnet, daß man Alkine mit Benzyl-Halogeniden in Gegenwart einer Palladiumverbindung und schwachen Basen umsetzt und einige neue 3-Aryl-propine.(EN) The invention relates to a process for producing 3-aryl propines in which alkines are reacted with benzyl halides in the presence of a palladium compound and weak bases, and to some novel 3-aryl propines.(FR) La présente invention concerne un procédé de production de 3-arylpropines, caractérisé en ce que l'on fait réagir des alkynes avec des haloïdes de benzyle en présence d'un composé de palladium et de bases faibles, ainsi que quelques nouvelles 3-arylpropines.

  该发明涉及一种制备3-甲基-苯基丙烯的方法，在该方法中，卤代烯与苯基卤化物在Pd化合物和弱碱的存在下反应，得到一些新型的3-甲基-苯基丙烯。
• LUNDKVIST, J. R. MICHAEL;RINGDAHL, BJORN;HACKSELL, ULI, J. MED. CHEM., 32,(1989) N, C. 863-869
  作者：LUNDKVIST, J. R. MICHAEL、RINGDAHL, BJORN、HACKSELL, ULI

  DOI：——

  日期：——
• VERFAHREN ZUR HERSTELLUNG VON 3-ARYL-PROPINEN UND NEUE 3-ARYL-PROPINE
  申请人：BAYER AG

  公开号：EP0741681B1

  公开（公告）日：1998-05-20
• Fischer Carbene Pentannulation with Alkynes Having Adjacent Carbonate or Acyloxy Groups: Synthesis of 3-Substituted 1-Indanones
  作者：Rodney A. Fernandes、Sachin P. Gholap、Vijay P. Chavan、Akeel S. Saiyed、Shubhankar Bhattacharyya

  DOI：10.1021/acs.orglett.0c00901

  日期：2020.5.1

  Various aryl Fischer carbenes reacted with alkynes having adjacent acyloxy or carbonate groups to regioselectively deliver 3-substituted 1-indanones. The acyloxy or carbonate group probably coordinates with the Cr metal to give a tetra-coordinated chromium complex forming a six-membered ring that retards CO insertion for ketene formation, which is required for benzannulation. Alternatively, the ortho

  各种芳基菲舍尔卡宾烯与具有相邻酰氧基或碳酸酯基团的炔反应，以区域选择性地递送3-取代的1-茚满酮。酰氧基或碳酸酯基团可能与Cr金属配位，得到四配位的铬络合物，形成六元环，该环阻碍了烯键形成所需的CO插入乙烯酮。可选地，邻位芳基环的进攻导致戊环化，从而提供区域选择性的3-取代的1-茚满酮。该方法扩展到3-表位-异泛醇的核心结构的合成。
• Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide
  作者：J. R. Michael Lundkvist、Bjorn Ringdahl、Uli Hacksell

  DOI：10.1021/jm00124a022

  日期：1989.4

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.