5(Z)-(bromomethylidene)tetrahydro-2-furanone | 79054-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 5(Z)-(bromomethylidene)tetrahydro-2-furanone
• 英文别名: (5Z)-5-(bromomethylidene)oxolan-2-one
• CAS: 79054-18-5
• 化学式: C₅H₅BrO₂
• 分子量: 176.997
• InChiKey: RJKPOGXUGUMJET-ARJAWSKDSA-N

物化性质

• 沸点：
  241.9±33.0 °C(Predicted)
• 密度：
  1.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  炔丙基脲 在 sodium hydroxide 、 Hg(II) trifluoroacetate 、 溴 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 46.0h， 生成 5(Z)-(bromomethylidene)tetrahydro-2-furanone
  参考文献：
  名称：

  Synthesis of halo enol lactones. Mechanism-based inactivators of serine proteases

  摘要：

  DOI：

  10.1021/ja00408a030

文献信息

• Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between AuI and AuIII
  作者：Hassina Harkat、Albert Yénimégué Dembelé、Jean-Marc Weibel、Aurélien Blanc、Patrick Pale

  DOI：10.1016/j.tet.2008.10.112

  日期：2009.2

  ω-Acetylenic acids, substituted or not at their acetylenic end, could be efficiently cyclized to γ- or δ-alkylidene lactones in the presence of AuCl and K2CO3. In contrast AuCl3 led to lactone dimers, probably through cyclization and reductive dimerization. These AuI and AuIII catalyzed cyclizations were totally regioselective and most often highly stereoselective.

  在AuCl和K 2 CO 3的存在下，可以在其乙炔基末端取代或不取代的ω-乙炔酸有效地环化为γ-或δ-亚烷基内酯。相反，AuCl 3可能通过环化和还原性二聚而导致内酯二聚体。这些Au I和Au III催化的环化反应完全是区域选择性的，并且通常是高度立体选择性的。
• Cyclisation of Alkynyl Alcohols and Carboxylic Acids Mediated by N‐Heterocyclic Carbene Copper(I) Complexes
  作者：Chaleena Pimpasri、Xiurong Luo、Shuai Yang、Silvia Díez‐González

  DOI：10.1002/adsc.202301181

  日期：2024.2.20

  economy thanks to the intramolecular reaction of alcohols and carboxylic acids with unsaturated carbon−carbon bonds using metal catalysis. Powerful as they are, these reactions often suffer from regioselectivity issues (endo/exo selectivity) and require rare precious metals or elaborated ligands.7 Palladium or rhodium remain popular choices for these reactions, but gold catalysts have lately gained predominance

  介绍 炔烃和烯烃之间 X−H 键的加成是有机合成化学中的一个基本转变，在分子内进行时可以得到重要的杂环。1, 2环状烯醇醚和内酯由于其独特的反应性和在生物活性化合物中反复出现，本身就是重要的基序。3-6由于醇和羧酸在金属催化作用下与不饱和碳碳键发生分子内反应，因此可以以 100% 原子经济性有效制备这些化合物。尽管这些反应功能强大，但通常会遇到区域选择性问题（内/外选择性），并且需要稀有的贵金属或精心设计的配体。7钯或铑仍然是这些反应的热门选择，但金催化剂最近在该领域占据了主导地位，允许分子间和分子内反应，通常在温和的反应条件下进行。8, 9事实上，Teles 关于醇与炔烃加成的开创性报告通常被认为是导致本世纪初金催化广泛流行的火花。10 第 11 族中的其他金属在这方面受到的关注相对较少。值得注意的是，报道的银介导的加氢烷氧基化使用简单的银盐（有时是化学计量的）11, 12，而辅助配体对
• Synthesis of halo enol lactones. Mechanism-based inactivators of serine proteases
  作者：Grant A. Krafft、John A. Katzenellenbogen

  DOI：10.1021/ja00408a030

  日期：1981.9
• A mild access to γ- or δ-alkylidene lactones through gold catalysis
  作者：Hassina Harkat、Jean-Marc Weibel、Patrick Pale

  DOI：10.1016/j.tetlet.2006.06.129

  日期：2006.8

  omega-Acetylenic acids are efficiently and stereo selectively converted to the corresponding enol lactones in the presence of catalytic amounts of AuCl and K2CO3. (c) 2006 Elsevier Ltd. All rights reserved.
• Stereoselective Z- and E-bromoenol lactonization of alkynoic acids
  作者：Wei Dai、John A. Katzenellenbogen

  DOI：10.1021/jo00024a035

  日期：1991.11

  We have found that treatment of the silver salt of a 4- or 5-terminal alkynoic acid with bromine results in clean formation of the corresponding Z-bromo enol lactone, the result of a formal cis addition of carboxylate and bromine across the triple bond. This Z-bromo enol lactonization is highly stereoselective and gives good yields in systems that bear substituents on the internal methylene groups; yields with unsubstituted or terminally substituted alkynoic acids are modest. The E-bromo enol lactonization reaction, reported by us previously (Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459), has a broader scope and, with modifications, can be performed with high reliability. Mercury(II) salts equilibrate the Z- and E-bromo enol lactones, presumedly by a mercuric ion addition-elimination mechanism. These three reactions provide access to an array of stereoisomeric bromo enol lactone systems.