trans-4-methyl-5-(2-propenyl)tetrahydro-2-furanone | 112423-33-3

• 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: trans-4-methyl-5-(2-propenyl)tetrahydro-2-furanone
• 英文别名: (4R,5S)-4-methyl-5-prop-2-enyloxolan-2-one
• CAS: 112423-33-3
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: HLUUBEFBTHTQRB-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  bromoacetaldehyde 1-vinylbut-3-enyl ethyl acetal 在 jones' reagent 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 生成 trans-4-methyl-5-(2-propenyl)tetrahydro-2-furanone
  参考文献：
  名称：

  取代基对自由基诱导的3-羟基己-1,5-二烯丙基溴缩醛环化的影响

  摘要：

  3-羟基己基1,5-二烯丙基溴缩醛的自由基环化产生单环或双环产物，具体取决于C-2上存在的取代基；描述了（+）-依加醇化物的合成。

  DOI：

  10.1039/c39890001824

文献信息

• A new strategy for the preparation of an active Mn(0) and its use for radical cyclization reactions
  作者：Jun Tang、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1016/s0040-4020(98)01205-8

  日期：1999.2

  Reduction of Li2MnCl4 with magnesium in THF afforded a fairly active manganese species which readily initiated radical cyclization of 2-iodoethanal allylic acetals at room temperature. The corresponding 2-bromoethanal acetals also provided the same cyclized products upon treatment with the activated manganese reagent at reflux in THF. This reagent can also be used to induce tandem radical cyclizations

  用THF中的镁还原Li 2 MnCl 4得到了相当活泼的锰，该锰易于在室温下引发2-碘乙烷缩醛烯丙基缩醛的自由基环化反应。在活化的锰试剂在THF中回流处理后，相应的2-溴乙烷缩醛也提供了相同的环化产物。该试剂也可用于诱导串联自由基环化，并且和模式均可用于使产物具有关于环连接的反立体化学。此外，还研究了分子内类型的该试剂的顺序生成和利用自由基和阴离子物种。
• Formation of Organomagnesium Compounds via EtMgBr-Mediated Radical Cyclization of Allyl β-Iodoacetals
  作者：Atsushi Inoue、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/ol991403a

  日期：2000.3.1

  [GRAPHICS]Treatment of allyl beta-iodoacetals with ethylmagnesium bromide in THF provided tetrahydrofuran derivatives in good yields. On the other hand, the reaction in DME provided tetrahydrofuranylmethylmagnesium compounds in good yields.
• Kunz, Thomas; Janowitz, Agnes; Reissig, Hans-Ulrich, Chemische Berichte, 1989, vol. 122, p. 2165 - 2176
  作者：Kunz, Thomas、Janowitz, Agnes、Reissig, Hans-Ulrich

  DOI：——

  日期：——
• Ester groups as effective ligands in chelate-controlled additions of cuprates and Grignard reagents to chiral .beta.-formyl esters to form .gamma.-lactones.
  作者：Hans Ulrich Reissig、Hubert Angert、Thomas Kunz、Agnes Janowitz、Gabriele Handke、Emanuel Bruce-Adjei

  DOI：10.1021/jo00075a022

  日期：1993.11

  Addition of cuprates to chiral methyl beta-formyl carboxylates 1a-1d provided gamma-lactones 2-7 in excellent trans-selectivity. The high diastereofacial selectivity was only obtained employing diethyl ether as solvent while tetrahydrofuran gave inferior results. Similar solvent effects were observed in the additions of various Grignard reagents to 1a, which afforded gamma-lactones 2,3,12, and 13 in moderate trans-selectivity. The best solvent for these reactions was dichloromethane. The 1,3-induction of cuprate additions was studied by using aldehydes 8a-8c. The results obtained were interpreted in terms of chelate-controlled additions with formation of seven-membered ring chelates which involve both carbonyl functions of aldehyde 1 or 8. The function of ester groups as effective ligands of lithium or MgX cations may also be of importance for other stereoselective reactions employing organometallic reagents.
• Kunz, Thomas; Reissig, Hans-Ulrich, Angewandte Chemie, 1988, vol. 100, # 2, p. 297 - 298
  作者：Kunz, Thomas、Reissig, Hans-Ulrich

  DOI：——

  日期：——