α-acetyl-α-allyl-γ-butyrolactone | 114709-93-2

• 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: α-acetyl-α-allyl-γ-butyrolactone
• 英文别名: 2-acetyl-2-allyl-γ-butyrolactone；3-acetyl-3-allyldihydrofuran-2(3H)-one；3-Acetyl-3-allyl-dihydro-furan-2-one；3-acetyl-3-prop-2-enyloxolan-2-one
• CAS: 114709-93-2
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: BOMHYQNWTSAVMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-acetyl-α-allyl-γ-butyrolactone 在 lithium aluminium tetrahydride 、 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 2-((4S,5S)-5-Allyl-2,2,4-trimethyl-[1,3]dioxan-5-yl)-ethanol
  参考文献：
  名称：

  STUDIES ON THE DIASTEREO- SELECTIVE REDUCTION OF 2-ACETYL-2-ALKYL- γ-BUTYROLACTONES WITH BORON HYDRIDES*

  摘要：

  Reduction of 2-acetyl-2-alkyl-gamma-butyrolactone derivatives with boron hydrides in the presence and absence of several chelating agents were studied. This process is influenced more by steric than chelation factors, yielding the isomeric alcohols syn (13-23) and anti (14-24) in good diastereomeric excess.

  DOI：

  10.1081/scc-120002396
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 生成 α-acetyl-α-allyl-γ-butyrolactone
  参考文献：
  名称：

  INABA, AKIXIKO;AOKI, XIDEHE;INOUEH, SINDZI

  摘要：

  DOI：

文献信息

• Direct Allylation of Active Methylene Compounds with Allylic Alcohols by Use of Palladium/Phosphine-Borane Catalyst System
  作者：Aika Shimizu、Goki Hirata、Gen Onodera、Masanari Kimura

  DOI：10.1002/adsc.201800187

  日期：2018.5.16

  The C−C bond formation between active methylene compounds and allylic alcohols has been newly developed by using a palladium complex as a catalyst together with a phosphine‐borane ligand. The best phosphine‐borane ligand for this direct allylation has been revealed to be Ph2P(CH2)4(9‐BBN) to produce a variety of desirable allylated products in high yields.

  通过使用钯配合物与膦-硼烷配体作为催化剂，新开发了活性亚甲基化合物与烯丙基醇之间的C-C键形成。已经证明，用于这种直接烯丙基化的最佳膦硼烷配体是Ph 2 P（CH 2）4（9-BBN），可以高产率生产出各种理想的烯丙基化产物。
• A Palladium-Catalyzed Asymmetric Allylic Alkylation Approach to α-Quaternary γ-Butyrolactones
  作者：Marllon Nascimento de Oliveira、Jeremy Fournier、Stellios Arseniyadis、Janine Cossy

  DOI：10.1021/acs.orglett.6b02971

  日期：2017.1.6

  The Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) of enol carbonates derived from γ-butyrolactones is reported, affording the corresponding enantioenriched α,α′-disubstituted γ-butyrolactones in both high yields and high enantioselectivities (up to 94% ee). This method was eventually applied to the synthesis of chiral spirocyclic compounds.

  据报道，由γ-丁内酯衍生的烯醇碳酸酯的Pd催化不对称烯丙基烷基化（Pd-AAA），可提供高产率和高对映选择性（高达94％ee）的相应的对映体富集的α，α'-二取代γ-丁内酯。 。该方法最终应用于手性螺环化合物的合成。
• Remarkable rate enhancement of palladium-catalyzed allylic alkylation in water using a colloidal dispersion system
  作者：Shū Kobayashi、William W.-L Lam、Kei Manabe

  DOI：10.1016/s0040-4039(00)01027-3

  日期：2000.8

  The rate of palladium-catalyzed allylic alkylation was dramatically enhanced in a colloidal dispersion system created by a neutral surfactant, Triton X-100, in water.

  在中性表面活性剂Triton X-100在水中形成的胶体分散体系中，钯催化的烯丙基烷基化速率大大提高。
• N-Heterocyclic olefins as efficient phase-transfer catalysts for base-promoted alkylation reactions
  作者：Marcus Blümel、Reece D. Crocker、Jason B. Harper、Dieter Enders、Thanh V. Nguyen

  DOI：10.1039/c6cc03771b

  日期：——

  N-Heterocyclic Olefins (NHOs) have very recently emerged as efficient promoters for several chemical reactions due to their strong Bronsted/Lewis basicities. Here we report the novel application of NHOs as efficient...

  N-杂环烯烃（NHOs）由于其强大的Bronsted / Lewis基础性，最近已成为多种化学反应的有效促进剂。在这里，我们将NHO的新颖应用报告为高效...
• Mn(III)-Based Oxidative Free-Radical Cyclizations of Unsaturated Ketones
  作者：Bridget McCarthy Cole、Luning Han、Barry B. Snider

  DOI：10.1021/jo961199u

  日期：1996.1.1

  free-radical cyclization of unsaturated ketones is a versatile synthetic procedure with broad applicability. For example, oxidation of cyclopentanone 1a with 2 equiv of Mn(OAc)(3).2H(2)O and 1 equiv of Cu(OAc)(2).H(2)O in AcOH at 80 degrees C for 1.5 h affords 75% of bicyclo[3.2.1]oct-3-en-8-one 8a and 15% of bicyclo[3.2.1]oct-2-en-8-one 9a. Bridged bicyclic ketones that cannot enolize further are isolated

  Mn（III）基的不饱和酮的氧化自由基环化是一种通用的合成方法，具有广泛的适用性。例如，在80摄氏度的条件下，在AcOH中用2当量的Mn（OAc）（3）.2H（2）O和1当量的Cu（OAc）（2）.H（2）O氧化环戊酮1a 1.5小时得到75％的双环[3.2.1] oct-3-en-8-one 8a和15％的双环[3.2.1] oct-2-en-8-one 9a。分离出不能进一步烯醇化的桥联双环酮，收率很高。可以烯化的单环β，γ-不饱和酮被进一步氧化，得到γ-乙酰氧基烯酮。从2-烯丙基环己酮（56a）以52％的收率形成双环[3.3.1] non-2-en-9-one（57a）表明，动力学控制的烯醇化是α-酮自由基形成过程中的决定速率的步骤。各种各样的示例描述了范围，限制，