2-methylene-4-pentenyl acetate | 83739-45-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-methylene-4-pentenyl acetate
• 英文别名: 2-methylidenepent-4-enyl acetate
• CAS: 83739-45-1
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: UQIUAPLWOBQSGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  乙酸烯丙酯 、 氯乙酸丙烯酯 以 四氢呋喃 为溶剂， 以17%的产率得到2-亚甲基-4-戊烯基氯乙酸酯
  参考文献：
  名称：

  Miyamo, Sotaro; Mori, Atsuo; Kato, Katsumi, Chemistry Letters, 1982, p. 1379 - 1382

  摘要：

  DOI：

文献信息

• Carboindation of Carbon−Carbon Triple Bonds:  Regioselective Indium-Mediated Allylation of Functionalized Alkynes and Transformation into Halogen-Substituted 1,4-Dienes
  作者：Ernst Klaps、Walther Schmid

  DOI：10.1021/jo9908593

  日期：1999.10.1

  By examining the allylindation of a series of substituted alkynes, the relationships between allylindation reactivity and alkyne structure were systematically investigated. While terminal alkynes with protected hydroxyl groups gave the corresponding allylated branched 1,4-dienes (Markovnikov products) within 5-6 h, the unprotected alkynols reacted markedly faster, requiring only 2-4 h of ultrasonication in THF to produce the 1,4-dienols in good yields. In the latter reactions, the regioisomeric outcome was found to depend on the distance between the hydroxyl group and the alkyne moiety: propargylic substrates gave linear 1,4-dienes (anti-Markovnikov products), suggesting the involvement of bicyclic "chelation-controlled" transition state, while 4-pentynol and higher homologues exclusively afforded the branched 1,4-dienes. Moreover, the proposed vinylic alpha,alpha-bis-indium intermediates from both protected and unprotected substrates were successfully quenched with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) to form tri- and tetrasubstituted dienes in good yields. Taken as a whole, these results illustrate the remarkable stability of the allylindium and vinylindium intermediates despite the presence of protic functionalities in the reaction mixture.
• Miyamo, Sotaro; Mori, Atsuo; Kato, Katsumi, Chemistry Letters, 1982, p. 1379 - 1382
  作者：Miyamo, Sotaro、Mori, Atsuo、Kato, Katsumi、Kawashima, Yasuhiko、Hashimoto, Harukichi

  DOI：——

  日期：——