(R)-[2-(hydroxymethyl)-6-methyl-4-oxo-4H-1,3-dioxin-2-yl]methyl acetate | 525600-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-[2-(hydroxymethyl)-6-methyl-4-oxo-4H-1,3-dioxin-2-yl]methyl acetate
• 英文别名: [(2R)-2-(hydroxymethyl)-4-methyl-6-oxo-1,3-dioxin-2-yl]methyl acetate
• CAS: 525600-76-4
• 化学式: C₉H₁₂O₆
• 分子量: 216.191
• InChiKey: GIIXLKDAPSLBAI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-[2-(hydroxymethyl)-6-methyl-4-oxo-4H-1,3-dioxin-2-yl]methyl acetate 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 (1S,2S,3S)-3-{3-[(acetyloxy)methyl]-2-hydroxy-2-methylcyclobutyl}propyl acetate
  参考文献：
  名称：

  Synthesis of optically active 1,3-dioxin-4-one derivatives having a hydroxymethyl group at the 2-position and their use for regio-, diastereo-, and enantioselective synthesis of substituted cyclobutanols

  摘要：

  A new method for preparing optically active 1,3-dioxin-4-one derivatives is presented. A series of prochiral 2,2-bis(hydroxymethyl)-1,3-dioxin-4-ones was synthesized by [4+2]cycloaddition of acylketene to protected 1,3-dihydroxy-2-propanone derivatives followed by deprotection of the hydroxyl groups. Desymmetrization of the prochiral dioxinones by lipase-catalyzed monoacetylation afforded optically active 2-(hydroxymethyl)dioxin ones. Intramolecular photo[2+2]cycloaddition of W-alkenyl esters of these alcohols provided an efficient method for regio-, diastereo-, and enantio selective synthesis of cyclobutanols. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00760-7
• 作为产物：
  描述：

  乙酸乙烯酯 、 2,2-bis(hydroxymethyl)-6-methyl-4H-1,3-dioxin-4-one 在 Lipase PS 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 (R)-[2-(hydroxymethyl)-6-methyl-4-oxo-4H-1,3-dioxin-2-yl]methyl acetate 、 (S)-[2-(hydroxymethyl)-6-methyl-4-oxo-4H-1,3-dioxin-2-yl]methyl acetate 、 2,2-bis[(acetoxy)methyl]-6-methyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Synthesis of optically active 1,3-dioxin-4-one derivatives having a hydroxymethyl group at the 2-position and their use for regio-, diastereo-, and enantioselective synthesis of substituted cyclobutanols

  摘要：

  A new method for preparing optically active 1,3-dioxin-4-one derivatives is presented. A series of prochiral 2,2-bis(hydroxymethyl)-1,3-dioxin-4-ones was synthesized by [4+2]cycloaddition of acylketene to protected 1,3-dihydroxy-2-propanone derivatives followed by deprotection of the hydroxyl groups. Desymmetrization of the prochiral dioxinones by lipase-catalyzed monoacetylation afforded optically active 2-(hydroxymethyl)dioxin ones. Intramolecular photo[2+2]cycloaddition of W-alkenyl esters of these alcohols provided an efficient method for regio-, diastereo-, and enantio selective synthesis of cyclobutanols. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00760-7