(-)-(1S,4S,5R)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one | 169870-98-8

• 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: (-)-(1S,4S,5R)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo<3.2.0>heptan-2-one
• 英文别名: (-)-(1S,4S,5R)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-3-oxabicyclo[3.2.0]heptan-2-one；[(1R,2S,5S)-6,6,7,7-tetramethyl-4-oxo-3-oxabicyclo[3.2.0]heptan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 169870-98-8
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: MZKKIIQVZQOMNY-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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 乙醚 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 (-)-(1S,4S,5R)-4-pivaloyloxymethyl-6,6,7,7-tetramethyl-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

• [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。
• Stereoselective |2+2| photocycloaddition of chiral 2(5H)-furanones to alkenes
  作者：Ramón Alibés、José L. Bourdelande、Josep Font

  DOI：10.1016/s0957-4166(00)80035-x

  日期：1991.1

  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.