(-)-(S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone | 84077-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (-)-(S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone
• 英文别名: (-)-3-methyl-4-pivaloyloxymethyl-2-buten-4-olide；2(5H)-furanone；[(2S)-3-methyl-5-oxo-2H-furan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 84077-32-7
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: YYMOMDVXQQFQAE-MRVPVSSYSA-N

物化性质

• 熔点：
  65-67 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  321.4±15.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone 在 锌 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 10.83h， 生成 (1S)-1-[(1S,4R)-4-(1-hydroxy-1-methylethyl)-1-methyl-2-cyclobutenyl]ethane-1,2-diol
  参考文献：
  名称：

  Highly Efficient and Diastereoselective Synthesis of (+)-Lineatin

  摘要：

  A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercuration reaction.

  DOI：

  10.1021/ol0497032
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-5H-furan-2-one 以 1,4-二氧六环 为溶剂， 生成 (-)-(S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone
  参考文献：
  名称：

  Highly efficient approach to (+)-grandisol via a diastereoselective |2+2| Photocycloaddition to 2(5H)-furanones

  摘要：

  A new approach to (+) and (-)-grandisol is described through a diastereoselective photocycloaddition of ethylene to an easily available homochiral butenolide. Optically pure intermediates are obtained.

  DOI：

  10.1016/s0040-4039(00)60151-x

文献信息

• An asymmetric synthesis of cis, anti, cis-tricyclo[5,3,0,02,6]decanes applying γ-hydroxymethyl-γ-butyrolactone as a chiral synthon. First asymmetric total synthesis of (−)-β-bourbonene
  作者：Kiyoshi Tomioka、Masahide Tanaka、Kenji Koga

  DOI：10.1016/s0040-4039(00)87626-1

  日期：1982.1

  The asymmetric total synthesis of cis, anti, cis-tricyclo[5,3,0,02,6]decane sesquiterpene β-bourbonene is described. The key (2+2) photocycloaddition was carried out applying the optically pure butenolide derivative 6b as a chiral synthon.

  描述了顺式，反式，顺式-三环[5,3,0,0 2,6 ]癸烷倍半萜烯β-波本烯的不对称全合成。使用光学纯的丁烯内酯衍生物6b作为手性合成子进行关键的（2 + 2）光环加成。
• Regio- and diastereoselectivity studies on the photocycloaddition of ketene diethyl acetal to chiral 2(5H)-furanones
  作者：Albert Rustullet、Marta Racamonde、Ramon Alibés、Pedro de March、Marta Figueredo、Josep Font

  DOI：10.1016/j.tet.2008.07.082

  日期：2008.9

  The photochemical [2+2] cycloaddition of 1,1-diethoxyethylene to chiral 2(5H)-furanones is investigated. The effect of the substituents of the lactone and the polarity of the solvents on the chemical yield, regioselectivity, and facial diastereoselectivity is evaluated. The reactions in ether proceed with excellent regioselectivity and good yields. Hydrolysis of the ketal group of the major cycloadducts

  研究了1,1-二乙氧基乙烯与手性2（5 H）-呋喃酮的光化学[2 + 2]环加成反应。评估了内酯的取代基和溶剂的极性对化学收率，区域选择性和面部非对映选择性的影响。在乙醚中的反应以优异的区域选择性和良好的收率进行。主要环加合物的缩酮基团的水解得到与γ-内酯融合的对映体纯的环丁酮。
• Photochemical Cycloaddition of Mono-, 1,1-, and 1,2-Disubstituted Olefins to a Chiral 2(5<i>H</i>)-Furanone. Diastereoselective Synthesis of (+)-Lineatin
  作者：Marta Racamonde、Ramon Alibés、Marta Figueredo、Josep Font、Pedro de March

  DOI：10.1021/jo800970u

  日期：2008.8.1

  The photochemical [2 + 2] cycloaddition of (S)-4-methyl-5-O-pivaloyloxymethyl-2(5H)-furanone, 5, to vinyl acetate, vinyl pivalate, tert-butyl vinyl ether, 1,1-diethoxyethylene, and (Z)- and (E)-1,2-dichloroethylene has been studied. A practical synthesis of (+)-lineatin from 5 has been developed via the functionalized cyclobutane 6.

  （S）-4-甲基-5 - O-新戊酰氧基甲基-2（5 H）-呋喃酮5的光化学[2 + 2]环加成到乙酸乙烯酯，新戊酸乙烯酯，叔丁基乙烯基醚1，1-二乙氧基乙烯，（Z）-和（E）-1,2-二氯乙烯已被研究。通过官能化的环丁烷6已经开发了由5合成（+）-lineatin的实用方法。
• Photocycloaddition of (Z)-1,2-dichloroethylene to enantiopure 2(5H)-furanones: an efficient strategy for the diastereoselective synthesis of cyclobutane and cyclobutene derivatives
  作者：Ramon Alibés、Pedro de March、Marta Figueredo、Josep Font、Marta Racamonde、Albert Rustullet、Angel Alvarez-Larena、Juan F. Piniella、Teodor Parella

  DOI：10.1016/s0040-4039(02)02528-5

  日期：2003.1

  A highly stereoselective and efficient synthetic approach to cyclobutane and cyclobutene derivatives has been developed consisting of a [2+2] photochemical cycloaddition of chiral 2(5H)-furanones to (Z)-1,2-dichloroethylene followed by dihydrodehalogenation or dihaloelimination.

  已经开发了对环丁烷和环丁烯衍生物的高度立体选择性和有效的合成方法，该方法包括将手性2（5 H）-呋喃酮与（Z）-1,2-二氯乙烯进行[2 + 2]光化学环加成，然后进行二氢脱卤或二卤代消除。
• Photochemical [2 + 2] Cycloaddition of Acetylene to Chiral 2(5<i>H</i>)-Furanones
  作者：Ramon Alibés、Pedro de March、Marta Figueredo、Josep Font、Xiaolin Fu、Marta Racamonde、Ángel Álvarez-Larena、Juan F. Piniella

  DOI：10.1021/jo0264731

  日期：2003.2.1

  The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C(2)-symmetric bis(lactone) as the substrate

  研究了乙炔与手性2（5H）-呋喃酮的[2 + 2]光环加成反应。评估了立体中心取代基对化学收率和面部非对映选择性的影响，以及4-甲基的影响。提出了一种基于简单理论构象分析的机械方案。使用C（2）对称双（内酯）作为底物，发现非对映异构体的过量率高于98％。