6(E)-bromomethylidenetetrahydro-2-pyrone | 79054-08-3

• 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: 6(E)-bromomethylidenetetrahydro-2-pyrone
• 英文别名: 6(E)-(bromomethylidene)tetrahydro-2-pyranone；(E)-6-(bromomethylene)tetrahydro-2H-pyran-2-one；(6E)-6-(bromomethylidene)oxan-2-one
• CAS: 79054-08-3
• 化学式: C₆H₇BrO₂
• 分子量: 191.024
• InChiKey: LCRYFNQWSFRVCH-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 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

• 作为产物：
  描述：

  5-己炔酸 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 6(E)-bromomethylidenetetrahydro-2-pyrone
  参考文献：
  名称：

  Haloenol pyranones and morpholinones as antineoplastic agents of prostate cancer

  摘要：

  Haloenol pyran-2-ones and morpholin-2-ones were synthesized and evaluated as inhibitors of cell growth in two different prostate human cancer cell lines (PC-3 and LNCaP). Analogs derived from Land D-phenylglycine were found to be the most effective antagonists of LNCaP and PC-3 cell growth. Additional studies reveal that the inhibitors induced G2/M arrest and the (S)-enantiomer of the phenylglycine-based derivatives was a more potent inhibitor of cytosolic iPLA(2)beta. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.05.038

文献信息

• Method of selectively inhibiting calcium-independent myocardial
  申请人：Washington University

  公开号：US05208244A1

  公开（公告）日：1993-05-04

  Inhibition of calcium-independent myocardial phospholipase A.sub.2 is shown for compounds of the formula: ##STR1## wherein R and R.sup.1 independently represent hydrogen and halogen, alkyl, alkenyl and alkynyl radicals; R.sup.2 represents aryl, aryloxy, and heteroaryl radicals; and X is 1 or 2.

  该公式的化合物显示了对无钙心肌磷脂酶A.sub.2的抑制作用: ## STR1 ## 其中R和R.sup.1独立地表示氢和卤素，烷基，烯基和炔基基团; R.sup.2表示芳基，芳氧基和杂环芳基基团; X为1或2。
• Zinc-Catalyzed Cyclization of Alkynyl Derivatives: Substrate Scope and Mechanistic Insights
  作者：Marc Martínez de Sarasa Buchaca、Miguel A. Gaona、Luis F. Sánchez-Barba、Andrés Garcés、Ana M. Rodríguez、Antonio Rodríguez-Diéguez、Felipe de la Cruz-Martínez、José A. Castro-Osma、Agustín Lara-Sánchez

  DOI：10.1021/acs.inorgchem.4c00832

  日期：2024.7.29

  lactone products under mild reaction conditions. Kinetic studies have been performed and confirmed that reactions are first-order in [catalyst] and zero-order in [alkynyl substrate]. DFT calculations supported a reaction mechanism through the formation of the catalytically active species, an alkoxide-zinc intermediate, by a protonolysis reaction of the Zn–alkyl bond with the alcohol group of the substrate

  由乙酰胺/硫代乙酰胺杂蝎酸酯配体支持的新型烷基锌配合物已成功合成并表征。这些配合物表现出不同的配位模式，具体取决于乙酰胺/硫代乙酰胺部分的电子和空间效应。它们的催化活性已针对炔醇/酸底物的加氢元素化反应进行了测试，在温和的反应条件下提供了相应的烯醇醚/不饱和内酯产物。动力学研究已进行并证实，反应在[催化剂]中是一级反应，在[炔基底物]中是零级反应。 DFT 计算支持通过 Zn-烷基键与底物醇基的质子解反应形成催化活性物质（醇盐-锌中间体）的反应机制。基于实验和理论结果，提出了催化循环。
• 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
• 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.
• US5208244A
  申请人：——

  公开号：US5208244A

  公开（公告）日：1993-05-04