5(E)-(iodomethylene)tetrahydro-2-furanone | 93040-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 5(E)-(iodomethylene)tetrahydro-2-furanone
• 英文别名: 5(E)-iodomethylidenetetrahydro-2-furanone；(5E)-5-(iodomethylidene)oxolan-2-one
• CAS: 93040-51-8
• 化学式: C₅H₅IO₂
• 分子量: 223.998
• InChiKey: XIPQQPOTDOENIA-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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

• 作为反应物：
  描述：

  5(E)-(iodomethylene)tetrahydro-2-furanone 在 potassium cyanide 、 bis(triphenylphosphine)palladium(II)-chloride 、 silver nitrate 、 copper(l) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 6.5h， 生成 5(E)-prop-2-ynylidenetetrahydro-2-furanone
  参考文献：
  名称：

  Ynenol lactones: synthesis and investigation of reactions relevant to their inactivation of serine proteases

  摘要：

  DOI：

  10.1021/ja00278a038
• 作为产物：
  描述：

  炔丙基脲 在 氧气 、 四丁基碘化铵 、 sodium nitrite 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 18.0h， 以64%的产率得到5(E)-(iodomethylene)tetrahydro-2-furanone
  参考文献：
  名称：

  Sodium nitrite (NaNO2) catalysed iodo-cyclisation of alkenes and alkynes using molecular oxygen

  摘要：

  We have developed a convenient iodo-cyclisation reaction using NaNO(2) as catalyst and molecular oxygen as the terminal oxidant. The reactive species, acetyl hypoiodite (IOAc), was generated in situ from TBAI and AcOH. The iodo-cyclisation reaction with a range of alkenes and alkynes gave good to excellent yields. Iodo-amination products can also be obtained using carbarnates prepared from commercially available allylic alcohols and alkynic alcohols. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.013

文献信息

• Ynenolactone protease inhibitors
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04602006A1

  公开（公告）日：1986-07-22

  Compounds of the formula ##STR1## wherein n is 1-3; R.sup.1, R.sup.2 and R.sup.3 are the same or different and are hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl or aryl lower alkyl wherein when aryl is phenyl it is unsubstituted or independently substituted with one or more halo, lower alkyl or lower alkoxy groups; and R.sup.4 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, trialkylsilyl, aryl or aryl lower alkyl wherein when aryl is phenyl it is unsubstituted or independently substituted by one or more halo, lower alkyl or lower alkoxy groups; excluding those compounds wherein R.sup.1 and R.sup.2 are hydrogen and R.sup.4 is ethyl, propyl or butyl. These compounds are useful as protease inhibitors.

  公式为##STR1##的化合物，其中n为1-3；R.sup.1、R.sup.2和R.sup.3相同或不同，可以是氢、低烷基、低烯烃基、低炔基、芳基或芳基低烷基，其中当芳基为苯基时，它未取代或独立地取代有一个或多个卤素、低烷基或低烷氧基；而R.sup.4为氢、低烷基、低烯烃基、低炔基、三烷基硅基、芳基或芳基低烷基，其中当芳基为苯基时，它未取代或独立地取代有一个或多个卤素、低烷基或低烷氧基；不包括那些其中R.sup.1和R.sup.2为氢且R.sup.4为乙基、丙基或丁基的化合物。这些化合物可用作蛋白酶抑制剂。
• Easy access to 5-(E)-alkynylidene tetrahydro-2 furanones by a palladium catalyzed process
  作者：Didier Bouyssi、Jacques Gore、Geneviéve Balme

  DOI：10.1016/s0040-4039(00)78865-4

  日期：1992.5

  Biologically active ynenol lactones 1 are stereospecifically obtained when gamma-acetylenic carboxylates are reacted with 1-bromo 1-alkynes in the presence of a palladium(0)-phosphine complex. The reaction is effective only with the potassium carboxylate and the nature of the phosphine is essential for the cyclisation process.
• Novel suicide inhibitors of serine proteinases. Inactivation of human leukocyte elastase by ynenol lactones
  作者：Tim Fat Tam、Robin W. Spencer、Everton M. Thomas、Leslie J. Copp、Allen Krantz

  DOI：10.1021/ja00334a068

  日期：1984.10
• Iodobenzene-catalysed iodolactonisation using sodium perborate monohydrate as oxidant
  作者：Hongjun Liu、Choon-Hong Tan

  DOI：10.1016/j.tetlet.2007.09.078

  日期：2007.11

  A convenient approach has been developed for iodolactonisation using iodobenzene as catalyst. The active reagent was generated in situ with tetra-n-butylammonium iodide (TBAI) and hypervalent iodine reagent, diacetoxyiodobenzene (PIDA). PIDA, in turn, was generated in situ using a catalytic amount of iodobenzene with sodium perborate monohydrate as the stoichiometric oxidant. A variety of olefinic acids including delta-pentenoic acids, delta-pentynoic acids and delta-hexynoic acid gave high yields of lactones using this methodology. (C) 2007 Elsevier Ltd. All rights reserved.
• TAM, TIM, FAT;SPENCER, R. W.;THOMAS, E. M.;COPP, L. J.;KRANTZ, A., J. AMER. CHEM.SOC., 1984, 106, N 22, 6849-6851
  作者：TAM, TIM, FAT、SPENCER, R. W.、THOMAS, E. M.、COPP, L. J.、KRANTZ, A.

  DOI：——

  日期：——