3-allyldihydrofuran-2-one | 10491-63-1

• 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: 3-allyldihydrofuran-2-one
• 英文别名: α-allyl-γ-butyrolactone；3-Allyl-2,3,4,5-tetrahydrofuran-2-one；2-allyl-γ-butyrolactone；3-allyldihydrofuran-2(3H)-one；3-allyl-dihydro-furan-2-one；allyldihydrofuran-2(3H)-one；3-(Prop-2-en-1-yl)oxolan-2-one；3-prop-2-enyloxolan-2-one
• CAS: 10491-63-1
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: USLBMAZTSPYPLP-UHFFFAOYSA-N

物化性质

• 沸点：
  64-69 °C(Press: 1 Torr)
• 密度：
  0.9997 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  3-allyldihydrofuran-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4,5-dihydro-3-propyl-2(3H)-furanone
  参考文献：
  名称：

  Nickel-BINAP Catalyzed Enantioselective α-Arylation of α-Substituted γ-Butyrolactones

  摘要：

  A Ni(0)-BINAP system is utilized for the highly enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones with aryl chlorides and bromides. alpha-Quaternization is achieved in moderate to excellent yields. Furthermore, the rate accelerating effect caused by the addition of Zn(II) salts is investigated.

  DOI：

  10.1021/ja017545t
• 作为产物：
  描述：

  4-(allyloxy)-1-(pyrrolidin-1-yl)butan-1-one 在 2,4,6-三甲基吡啶 、 三氟甲磺酸酐 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 16.08h， 以90%的产率得到3-allyldihydrofuran-2-one
  参考文献：
  名称：

  原位生成的亚胺醚的双亲核/亲电捕获：走向功能化酰胺构件的合成。

  摘要：

  重新排列羽毛：将简单的线性酰胺通过转化为亚氨基酯转化为各种支化的官能化产物，然后依次用亲核试剂和亲电试剂进行处理（参见方案）。该方法利用了新颖的克莱森重排，并且芳族底物的使用极大地促进了中间体亚胺醚的形成。

  DOI：

  10.1002/chem.201203293

文献信息

• 2-Functionalized allyl tris(trimethylsilyl)silanes as radical-based allylating agents
  作者：Chryssostomos Chatgilialoglu、Carla Ferreri、Marco Ballestri、Dennis P. Curran

  DOI：10.1016/0040-4039(96)01354-8

  日期：1996.8

  Radical allylations with 2-functionalized allyl tris(trimethylsilyl)silanes occur under mild conditions in good to excellent yield provided that the radical precursor and the silane have the appropriate electronic pairing. These reactions offer tin-free altermatives for transformations that are currently conducted with allyl stannanes.

  如果自由基前体和硅烷具有适当的电子配对，则在温和的条件下，以2官能化的烯丙基三（三甲基甲硅烷基）硅烷进行自由基烯丙基化反应会产生良好或极好的收率。这些反应为目前用烯丙基锡烷进行的转化提供了无锡替代品。
• Palladium-catalyzed preparation of α-allyl esters and α,β-unsaturated esters from saturated esters via their silyl acetals
  作者：Jro Tsuji、Kazuhiko Takahashi、Ichiro Minami、Isao Shimizu

  DOI：10.1016/s0040-4039(01)81518-5

  日期：——

  Reaction of ketene silyl acetals with allylic carbonates in the presence of palladium-phosphine catalyst in dioxane gives α-allyl esters in high yields. When the reaction is carried out with phosphine-free palladium catalyst in nitriles, α,β-unsaturated esters are obtained in good yields.

  在钯-膦催化剂存在下于二恶烷中使乙烯酮甲硅烷基缩醛与碳酸烯丙酯反应，以高收率得到α-烯丙基酯。当用无膦的钯催化剂在腈中进行反应时，以良好的产率获得α，β-不饱和酯。
• “Propylene spaced” allyl tin reagents: A new class of fluorous tin reagents for allylations under radical and metal-catalyzed conditions
  作者：Dennis P. Curran、Zhiyong Luo、Peter Degenkolb

  DOI：10.1016/s0960-894x(98)00435-1

  日期：1998.9

  A new generation of propylene-spaced fluorous allyltin reagents [(Rf(CH2)3)3SnCH2CH = CH2] is described. These succeed in radical allylations where their lower homologs (ethylene-spaced) fail, and they provide improved performance in transition metal catalyzed allylations. The reagents and byproducts are readily separated by simple fluorous-organic liquid-liquid or solid-liquid extractions.

  描述了新一代的丙烯间隔氟烯丙基锡试剂[（Rf（CH2）3）3SnCH2CH = CH2]。这些在低级同系物（乙烯间隔的）失效的自由基烯丙基化中成功，并且在过渡金属催化的烯丙基化中提供了改进的性能。试剂和副产物可通过简单的氟有机液-液或固-液萃取轻松分离。
• Lewis Acid Catalyzed Synthesis of α-Trifluoromethyl Esters and Lactones by Electrophilic Trifluoromethylation
  作者：Dmitry Katayev、Václav Matoušek、Raffael Koller、Antonio Togni

  DOI：10.1021/acs.orglett.5b03088

  日期：2015.12.4

  An electrophilic trifluoromethylation of ketene silyl acetals (KSAs) by hypervalent iodine reagents 1 and 2 has been developed. The reaction proceeds under very mild conditions in the presence of a catalytic amount of trimethylsilyl bis(trifluoromethanesulfonyl)imide (up to 2.5 mol %) as a Lewis acid providing a direct access to a variety of secondary, tertiary, and quaternary α-trifluoromethyl esters

  已经开发了由高价碘试剂1和2进行的乙烯酮甲硅烷基缩醛（KSAs）的亲电子三氟甲基化反应。反应在非常温和的条件下，在催化量的三甲基甲硅烷基双（三氟甲磺酰基）酰亚胺（至多2.5 mol％）的路易斯酸存在下进行，可直接获得各种仲，叔和季α-三氟甲基酯和内酯，收率高（高达98％）。
• Application of Enelike Reactions of Aldehydes with Vinyl Ethers:  A Stereoconvergent Synthesis of (±)-Phyllanthocin
  作者：Marco A. Ciufolini、Shuren Zhu、Melissa V. Deaton

  DOI：10.1021/jo971151w

  日期：1997.10.1

  (+/-)-Phyllanthocin has been synthesized through a key step involving the enelike reaction of an aldehyde with 2-methoxypropene recently developed in these laboratories. This work demonstrates that our chemistry is suitable for multistep synthetic applications, and it shows that stereocontrol in the creation of the phyllanthocin structure may be achieved by thermodynamic equilibration of both peripheral stereogenic carbons.

  (±)-Phyllanthocin 最近通过我们实验室开发的关键步骤合成而成，该步骤涉及醛类与 2-甲氧基丙烯之间的烯类反应。这项研究展示了我们的化学方法适用于多步骤合成应用，并表明在构建 phyllanthocin 结构时，可以通过两个外周手性碳的热力学平衡来实现立体控制。