2,2-bis(hydroxymethyl)-6-phenyl-4H-1,3-dioxin-4-one | 525600-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-bis(hydroxymethyl)-6-phenyl-4H-1,3-dioxin-4-one
• 英文别名: 2,2-Bis(hydroxymethyl)-6-phenyl-1,3-dioxin-4-one
• CAS: 525600-72-0
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: JHSAOHYGTRAUPW-UHFFFAOYSA-N

物化性质

• 沸点：
  487.2±45.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 2,2-bis(hydroxymethyl)-6-phenyl-4H-1,3-dioxin-4-one 在 Lipase PS 作用下， 以 乙腈 为溶剂， 反应 60.0h， 生成 (S)-[2-(hydroxymethyl)-6-phenyl-4-oxo-4H-1,3-dioxin-2-yl]methyl acetate 、 (R)-[2-(hydroxymethyl)-6-phenyl-4-oxo-4H-1,3-dioxin-2-yl]methyl acetate 、 2,2-bis[(acetoxy)methyl]-6-phenyl-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
• 作为产物：
  描述：

  5-benzoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 在 三氟乙酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 43.0h， 生成 2,2-bis(hydroxymethyl)-6-phenyl-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

文献信息

• 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
  作者：Masayuki Murakami、Hiroshi Kamaya、Chikara Kaneko、Masayuki Sato

  DOI：10.1016/s0957-4166(02)00760-7

  日期：2003.1

  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.