Prop-2-enyl 3-(2-methyl-4-oxo-1,3-dioxin-2-yl)propanoate | 133592-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Prop-2-enyl 3-(2-methyl-4-oxo-1,3-dioxin-2-yl)propanoate
• CAS: 133592-85-5
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: YKGDHZHFBJBITP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Prop-2-enyl 3-(2-methyl-4-oxo-1,3-dioxin-2-yl)propanoate 在 咪唑 、 水 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 134.0h， 生成 (1R,2R,3S)-1-acetoxymethyl-2-(tert-butyldiphenylsiloxy)-3-hydroxymethylcyclobutane
  参考文献：
  名称：

  Regio-, stereo-, and enantioselective synthesis of cyclobutanols by means of the photoaddition of 1,3-dioxin-4-ones and lipase-catalyzed acetylation

  摘要：

  Homochiral cis-2-hydroxymethylcyclobutanols, their all cis 3-methyl, and 4-hydroxymethyl derivatives were synthesized from 1,3-dioxin-4-ones via cyclobutane ring formation by [2+2]photocycloaddition, dioxanone ring cleavage, and reduction, followed by lipase-catalyzed kinetic resolution of the resulted cyclobutanols. The chiral cyclobutanols thus obtained have been converted to the corresponding gamma-lactones which are potential precursors for a series of biologically active compounds.

  DOI：

  10.1016/s0957-4166(00)80211-6
• 作为产物：
  描述：

  allyl 4-oxopentanoate 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 1.5h， 以62%的产率得到Prop-2-enyl 3-(2-methyl-4-oxo-1,3-dioxin-2-yl)propanoate
  参考文献：
  名称：

  Regio-, stereo-, and enantioselective synthesis of cyclobutanols by means of the photoaddition of 1,3-dioxin-4-ones and lipase-catalyzed acetylation

  摘要：

  Homochiral cis-2-hydroxymethylcyclobutanols, their all cis 3-methyl, and 4-hydroxymethyl derivatives were synthesized from 1,3-dioxin-4-ones via cyclobutane ring formation by [2+2]photocycloaddition, dioxanone ring cleavage, and reduction, followed by lipase-catalyzed kinetic resolution of the resulted cyclobutanols. The chiral cyclobutanols thus obtained have been converted to the corresponding gamma-lactones which are potential precursors for a series of biologically active compounds.

  DOI：

  10.1016/s0957-4166(00)80211-6

文献信息

• Regio- and Stereocontrols in the Photo[2+2]cycloaddition of 1,3-Dioxin-4-ones to Alkenes. Use of an Ester Group as the Connecting Unit in the Intramolecular Variant
  作者：Masayuki Sato、Yoshito Abe、Hirohide Ohuchi、Chikara Kaneko

  DOI：10.3987/com-90-5605

  日期：——

  Intramolecular photo[2+2]cycloaddition of dioxidones to alkene to give eight membered lactones proceeds with complete stereo- and high regioselectivities when an ester group presents as a linking unit between the acetal carbon and the double bond of the side chain. The successful separation of some dioxinones into the enantiomers indicates the method is useful for synthesis of enantiomerically pure compounds.