(+)-(R)-5-苯基呋喃-2-(5H)-酮 | 90366-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: (+)-(R)-5-苯基呋喃-2-(5H)-酮
• 英文名称: (+)-(R)-5-phenyl-furan-2-(5H)-one
• 英文别名: (5R)-5-phenyl-2(5H)-furanone；(R)-5-phenylfuran-2(5H)-one；(2R)-2-phenyl-2H-furan-5-one
• CAS: 90366-21-5
• 化学式: C₁₀H₈O₂
• 分子量: 160.172
• InChiKey: UXMKOLJFXKKWEQ-SECBINFHSA-N

物化性质

• 沸点：
  338.3±31.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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-苯基-3-丁烯酸 在 N-溴代丁二酰亚胺(NBS) 、 O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl] N-phenylcarbamothioate 、 三乙胺 作用下， 以 正己烷 、 氯仿 为溶剂， 反应 13.08h， 生成 (+)-(R)-5-苯基呋喃-2-(5H)-酮
  参考文献：
  名称：

  Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization

  摘要：

  The asymmetric cyclization of 4,4-disubstituted 3-butenoic acids is studied. Amino-thiocarbamates are used as the catalysts and N-bromosuccinimide is used as the stoichiometric halogen source. The resulting gamma-butanolide products are readily converted into the corresponding gamma-butenolides (up to 58% ee) derivatives in one-pot. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.009

文献信息

• Analytic and preparative resolution of recemic ?- and ?-lactones by chromatography on cellulose triacetate. Relationship between elution order and absolute configuration
  作者：Eric Francotte、Dieter Lohmann

  DOI：10.1002/hlca.19870700615

  日期：1987.9.23

  biologically active substances) have been separated chromatographically on the chiral phase cellulose triacetate, crystallographic form I (CTAI). For different series of five-membered-ring lactones, relationships have been found between the elution order of the enantiomers and their absolute configuration. Preparative resolutions of γ-Phenyl-γ-butyrolactone (1) and of the Pheromone component 5b have been carried

  在手性相三醋酸纤维素上色谱分离了各种手性五元和六元环内酯的对映异构体（重要的一类化合物（香料和信息素成分，生物活性物质合成中的关键中间体）） （CTAI）。对于不同系列的五元环内酯，已经发现对映异构体的洗脱顺序与其绝对构型之间的关系。进行了γ-苯基-γ-丁内酯（1）和信息素成分5b的制备拆分，以证明该方法可用于克级分离。
• A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization
  作者：Yu Kawamata、Takuya Hashimoto、Keiji Maruoka

  DOI：10.1021/jacs.6b01462

  日期：2016.4.27

  Chiral electrophilic selenium catalysts have been applied to catalytic asymmetric transformations of alkenes over the past two decades. However, highly enantioselective reactions with a broad substrate scope have not yet been developed. We report the first successful example of this reaction employing a catalyst based on a rigid indanol scaffold, which can be easily synthesized from a commercially

  在过去的二十年中，手性亲电硒催化剂已被应用于催化烯烃的不对称转化。然而，尚未开发出具有广泛底物范围的高度对映选择性反应。我们报告了该反应的第一个成功例子，该反应采用基于刚性茚满醇支架的催化剂，该支架可以很容易地从市售茚满酮合成。该反应在温和条件下有效地将 β,γ-不饱和羧酸转化为各种对映体富集的 γ-丁烯内酯。
• Chiral homoenolate anion equivalents: synthesis of optically pure 5-substituted furan-2(5H)-ones
  作者：Pierfrancesco Bravo、Paola Carrera、Giuseppe Resnati、Calimero Ticozzi

  DOI：10.1039/c39840000019

  日期：——

  Addition of the dianion of (+)-(R)-3-[(4-methylphenyl)sulphinyl]propionic acid (1) to aldehydes affords two main diastereoisomeric β-sulphinyl-γ-lactones, pyrolysis of which gives the two enantiomers of 5-substituted furan-2(5H)-ones in optically pure form.

  的二价阴离子的加成（+） - （[R）-3 - [（4-甲基苯基）亚磺酰基]丙酸（1）为醛，得到两个主要非对映异构β-亚-γ内酯，热解，其中给出了两种对映体光学纯净形式的5-取代的呋喃2（5 H）-ones。
• A Facile Solid-Phase Synthesis of Substituted 2(5<i>H</i>)-Furanones with Sulfone Traceless Linker
  作者：Shou-Ri Sheng、Pei-Gang Huang、Wei Zhou、Hai-Rong Luo、Shu-Ying Lin、Xiao-Ling Liu

  DOI：10.1055/s-2004-834804

  日期：——

  A novel solid-phase synthetic method for substituted 2(5H)-furanones with traceless sulfone linker strategy has been developed. The products were obtained in good yields and excellent purities.

  开发了一种新的固相合成方法，用于具有无痕砜接头策略的取代 2(5H)-呋喃酮。以良好的收率和优良的纯度获得了产物。
• A convergent asymmetric synthesis of γ-butenolides
  作者：Marc Renard、Léon A. Ghosez

  DOI：10.1016/s0040-4020(01)00078-3

  日期：2001.3

  The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded gamma -butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of gamma -butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin. (C) 2001 Elsevier Science Ltd. All rights reserved.