(1R,4S,5S)-4-pivaloyloxymethyl-3-oxabicyclo<3.2.0>heptan-2-one | 169871-03-8

• 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: (1R,4S,5S)-4-pivaloyloxymethyl-3-oxabicyclo<3.2.0>heptan-2-one
• 英文别名: (1R,4S,5S)-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one；[(1S,2S,5R)-4-oxo-3-oxabicyclo[3.2.0]heptan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 169871-03-8
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: KELXLYLMZNRMCF-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-5H-furan-2-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 30.5h， 生成 (1R,4S,5S)-4-pivaloyloxymethyl-3-oxabicyclo<3.2.0>heptan-2-one
  参考文献：
  名称：

  Stereoselective |2+2| photocycloaddition of chiral 2(5H)-furanones to alkenes

  摘要：

  The steric and stereoelectronic dependence of the diastereoselectivity in the photochemical \2 + 2\ cycloaddition of chiral 2(5H)-furanones to alkenes is investigated to prepare eventually cyclobutanic natural products. It is shown that the alkenes approach to different chiral 5-substituted 2(5H)-furanones mainly by the less hindered side.

  DOI：

  10.1016/s0957-4166(00)80035-x

文献信息

• 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。
• [2+2] Photocycloaddition of homochiral 2(5H)-furanones to alkenes. First step for an efficient and diastereoselective synthesis of (+)- and (−)-grandisol
  作者：Ramón Alibés、José L. Bourdelande、Josep Font、Anna Gregori、Teodoro Parella

  DOI：10.1016/0040-4020(95)00957-4

  日期：1996.1

  The [2+2] photocycloaddition of homochiral 5-alkyl-2(5H)-furanones to alkenes is studied in order to evaluate the influence of the stereogenie centre to induce facial diastereoselectivity. The major cycloadduct could be transformed, eventually, in (+)-grandisol, The existence of a charge-transfer complex between the furanone and electron rich substituted alkenes as well as the formation of a predominant

  研究了[2 + 2]同手性5-烷基-2（5H）-呋喃酮与烯烃的光环加成反应，以评估立体异构中心对诱导面部非对映选择性的影响。最终，主要的环加合物可以在（+）-大丁醇中转化。呋喃酮和富电子取代的烯烃之间存在电荷转移络合物，并且由于n-π在5-氧烷基呋喃酮中形成主要构象。相互作用进行了讨论。