γ,γ-Diallyl-γ-butyrolactone | 86816-19-5

• 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: γ,γ-Diallyl-γ-butyrolactone
• 英文别名: 5,5-diprop-2-enyldihydrofuran-2(3H)-one；5,5-diallyl-3,4-dihydrofuran-2-one；5,5-diallyl-dihydro-furan-2-one；5,5-Diallyl-dihydro-furan-2-on；5,5-Bis(prop-2-enyl)oxolan-2-one
• CAS: 86816-19-5
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: AAYCGBXTMAQVEP-UHFFFAOYSA-N

物化性质

• 沸点：
  46-50 °C(Press: 0.001 Torr)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  4
• 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

• 作为反应物：
  描述：

  γ,γ-Diallyl-γ-butyrolactone 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到1-Oxaspiro[4.4]non-7-en-2-one
  参考文献：
  名称：

  The Synthesis of Spirolactones Using Indium-Mediated Allylation of Cyclic Anhydrides and Ring-Closing Olefin Metathesis

  摘要：

  以环状酸酐为原料，通过铟介导的烯丙基化反应和闭环烯烃偏聚（RCM）反应等关键步骤制备出多种螺内酯。

  DOI：

  10.1055/s-2001-18084
• 作为产物：
  描述：

  丁二酸酐 、 烯丙基苯基醚 在 四(三苯基膦)钯 、 diethylzinc 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 以65%的产率得到γ,γ-Diallyl-γ-butyrolactone
  参考文献：
  名称：

  通过与烷基锌的烷基-烯丙基交换反应，将π-烯丙基钯用作亲核试剂

  摘要：

  羰基化合物（醛，酮，酯，内酯，酸酐）的烯丙基化在室温下通过羰基化合物，烯丙基苯甲酸酯或烯丙基苯醚，二乙基锌和催化量的Pd（0）-络合物的反应而顺利进行在N 2下于THF中。

  DOI：

  10.1016/s0040-4039(00)60415-x

文献信息

• Diastereoselective ruthenium-catalysed cycloisomerisation of diallyllactones: preparation of exo-methylene spirolactones
  作者：Mathieu Michaut、Maurice Santelli、Jean-Luc Parrain

  DOI：10.1016/s0040-4039(03)00144-8

  日期：2003.3

  Diallyllactones (obtained from cyclic anhydrides via a double allylation reaction promoted by titanium tetrachloride) were cycloisomerised using 5 mol% of cyclooctadienyl ruthenium dichloride in ethanol providing the corresponding exomethylene spirolactones in good yields, with moderated to good diastereomeric excess.

  使用5摩尔％的环辛二烯基二氯化钌在乙醇中的环异构化二烯丙基内酯（通过四氯化钛促进的双烯丙基化反应从环状酸酐中获得），以适当的收率提供适度至良好的非对映异构体过量的相应的外亚甲基螺内酯。
• Unsymmetrical Ketone Synthesis via a Three-Component Connection Reaction of Organozincs, Allylating Agents, and Carbon Monoxide
  作者：Kengo Yasui、Keigo Fugami、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1021/jo00110a047

  日期：1995.3

  A wide variety of organozincs (diethylzinc, alkylzinc halides, and organozincs 2, 5, and 9a-e, functionalized with ester and nitrile groups) undergo a three-component connection reaction with carbon monoxide and allylic benzoates or phosphates 1a-h to furnish unsymmetrical ketones, e.g., 3, 6, and 10, in good yields under 1 atm of carbon monoxide at ambient temperature by the catalysis of tetrakis(triphenylphosphine)palladium in THF/HMPA. The regio- and stereoselectivities of the present carbonylation show marked contrast to those reported for the palladium-catalyzed carbonylation of unsymmetrical allylic substrates. For example, the reaction of crotyl benzoate with octylzinc iodide provides all the possible stereo- and regioisomers, i.e., cis- and trans-2-butenyl and 1-methyl-2-propenyl octyl ketones in comparable amounts. The carbonylative coupling of carvyl phosphates, trans- and cis-1h, and gamma-zincio ester 5 is stereospecific and proceeds with inversion of configuration at the allylic stereocenters to furnish cis- and trans-6h, respectively, as single diastereomers. In the absence of HMPA, the reaction feature changes dramatically and lactones 12 and 13 (composed of organozincs, carbon monoxide, and allylating agents in the ratios of 1:1:2 and 2:1:1, respectively) and symmetrical keto diesters 14 (composed of 2 mol of organozincs and 1 mol of carbon monoxide) are formed in varying ratios depending on the reaction conditions. Synthetic scope of the unsymmetrical ketones and mechanistic rationale for these unique and unprecedented reaction behaviors are discussed.
• An efficient of Grignard-type procedure for the preparation of gem-diallylated compound
  作者：Kao-Hsien Shen、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1016/j.tetlet.2007.07.008

  日期：2007.9

  An efficient and a new procedure for the conversion of various carboxylic acid derivatives into the corresponding gemdiallylated compound under mild reaction condition has been developed. The triallyaluminum mediated Grignard-type addition of carboxylic acid derivative was utilized as a key operation to affect the transformation. The procedure is operationally simple, giving good to excellent product yields for a broad range of substrates. The chemoselectivity and regioselectivity of triallylaluminum were also demonstrated. (C) 2007 Elsevier Ltd. All rights reserved.
• Kasanski, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1903, vol. 35, p. 1184
  作者：Kasanski

  DOI：——

  日期：——
• Kasanski, Journal fur praktische Chemie (Leipzig 1954), 1905, vol. <2> 71, p. 249
  作者：Kasanski

  DOI：——

  日期：——