5-己基-3-甲基-二氢-呋喃-2-酮 | 77811-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 5-己基-3-甲基-二氢-呋喃-2-酮
• 英文名称: 5-hexyl-3-methyl-dihydro-furan-2-one
• 英文别名: 5-Hexyl-3-methyl-dihydro-furan-2-on；alphamethyl-gamma-n-hexyl-butyrolactone；5-hexyl-3-methyloxolan-2-one
• CAS: 77811-13-3
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: JVLVXEZBHVOZEK-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 1 Torr)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  4-bromo-2-methyl-decanoic acid ethyl ester 180.0 ℃ 、7.33 kPa 条件下， 生成 5-己基-3-甲基-二氢-呋喃-2-酮
  参考文献：
  名称：

  Kharasch; Skell; Fisher, Journal of the American Chemical Society, 1948, vol. 70, p. 1058

  摘要：

  DOI：

文献信息

• Free Radical Addition of 2-Bromoalkanoic Acids to Alkenes
  作者：Taichi Nakano、Mikio Kayama、Yoichiro Nagai

  DOI：10.1246/bcsj.60.1049

  日期：1987.3

  The benzoyl peroxide-catalyzed reaction of 2-bromoalkanoic acids such as bromoacetic, 2-bromopropionic, and 2-bromobutyric acid with 1-alkenes was found to proceed through the addition of the C–Br bond across the double bond followed by cyclization affording 4-alkanolides in good yields.

  发现过氧化苯甲酰催化的 2-溴链烷酸（如溴乙酸、2-溴丙酸和 2-溴丁酸）与 1-烯烃的反应是通过在双键上添加 C-Br 键，然后环化得到 4 -链烷醇收率良好。
• Method for Producing Alkoxycarbonylfluoroalkanesulfonic Acid Salt
  申请人：Hagiwara Yuji

  公开号：US20110207954A1

  公开（公告）日：2011-08-25

  In the present invention, a target alkoxycarbonylfluoroalkanesulfonic acid salt is obtained by using a halofluoroalkanoic acid ester as a starting raw material, sulfinating the halofluoroalkanoic acid ester in the presence of an amine (as a first step), and then, oxidizing the resulting sulfination product (as a second step). Further, an alkoxycarbonylfluoroalkanesulfinic acid onium salt, which is useful as a photoacid generator, is obtained by salt exchange reaction of the alkoxycarbonylfluoroalkanesulfonic acid salt.

  在本发明中，通过使用卤代氟烷羧酸酯作为起始原料，首先在胺的存在下对卤代氟烷羧酸酯进行磺化（作为第一步），然后氧化所得的磺化产物（作为第二步），获得目标烷氧羰基氟烷磺酸盐。此外，通过对烷氧羰基氟烷磺酸盐进行盐交换反应，得到一种用作光酸发生剂的烷氧羰基氟烷磺酸亚磺酸盐。
• FREE RADICAL ADDITION OF α-BROMOCARBOXYLIC ACIDS TO OLEFINS LEADING TO γ-BUTYROLACTONES
  作者：Taichi Nakano、Mikio Kayama、Hideyuki Matsumoto、Yoichiro Nagai

  DOI：10.1246/cl.1981.415

  日期：1981.3.5

  Benzoyl peroxide-catalyzed free radical addition of bromoacetic, α-bromopropionic, and α-bromobutyric acids to olefins took place under mild conditions to afford γ-alkyl-, γ-alkyl-α-methyl-, and γ-alkyl-α-ethyl-γ-butyrolactones in good yields.

  过氧化苯甲酰催化的溴乙酸、α-溴丙酸和 α-溴丁酸与烯烃的自由基加成反应在温和条件下发生，得到 γ-烷基-、γ-烷基-α-甲基-和 γ-烷基-α-乙基-γ-丁内酯收率良好。
• Investigations of the Scope and Mechanism of the Tandem Hydroesterification/Lactonization Reaction
  作者：Lijun Wang、Paul E. Floreancig

  DOI：10.1021/ol048378f

  日期：2004.11.1

  alcohols and 2-pyridylmethyl formate in the presence of Ru(3)(CO)(12) initiates a tandem sequence of hydroesterification and lactonization. Mechanistic studies suggest that regioselectivity and overall reaction efficiency are governed by the relative rates of reductive elimination and beta-hydride elimination for the alkylruthenium intermediates.

  在Ru（3）（CO）（12）存在的情况下加热烯丙基和均烯丙基醇和甲酸2-吡啶基甲基甲酸酯可引发氢化酯化和内酯化的串联序列。机理研究表明，区域选择性和整体反应效率受烷基钌中间体的相对消除和β-氢化物消除的相对速率支配。
• Preparation of gamma-butyrolactones
  申请人：Mobil Oil Corporation

  公开号：US04175089A1

  公开（公告）日：1979-11-20

  Gamma-butyrolactones are formed by reacting an olefin with a compound containing a carboxylate moiety having at least one hydrogen atom on the alpha carbon atom in the presence of an ion of manganese, cerium, or vanadium, the ion being in a valency state higher than its lowest valency state.

  Gamma-丁内酯是通过在锰、铈或钒的离子存在下，将含有至少一个α-碳原子上的氢原子的羧酸酯化合物与烯烃反应形成的，其中离子处于比其最低价态更高的价态。