3-(1,3-Dioxan-2-yl)-2-(1-hydroxyethyl)chromen-4-one | 203629-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(1,3-Dioxan-2-yl)-2-(1-hydroxyethyl)chromen-4-one
• CAS: 203629-50-9
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: MRLVEWUUZIEGPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1,3-Dioxan-2-yl)-2-(1-hydroxyethyl)chromen-4-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 Dimethyl 1-methyl-10-oxo-3,15-dioxatetracyclo[10.2.1.02,11.04,9]pentadeca-2(11),4,6,8,13-pentaene-13,14-dicarboxylate
  参考文献：
  名称：

  Synthesis and cycloadditions of 9H-furo[3,4-b][1]benzo(thio)pyran-9-ones: furan ring formation by a novel hydrolytically induced cycloreversion

  摘要：

  C-2 lithiation of acetals 2 followed by trapping with aldehydes gives 3. Subsequent unmasking of the acetal function provides furobenzo(thio)pyrans 4, cycloadditions of which have been investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00820-1
• 作为产物：
  描述：

  3-(1,3-Dioxan-2-yl)-4H-chromen-4-one 、 乙醛 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 为溶剂， 生成 3-(1,3-Dioxan-2-yl)-2-(1-hydroxyethyl)chromen-4-one
  参考文献：
  名称：

  Synthesis and cycloadditions of 9H-furo[3,4-b][1]benzo(thio)pyran-9-ones: furan ring formation by a novel hydrolytically induced cycloreversion

  摘要：

  C-2 lithiation of acetals 2 followed by trapping with aldehydes gives 3. Subsequent unmasking of the acetal function provides furobenzo(thio)pyrans 4, cycloadditions of which have been investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00820-1

文献信息

• The directed lithiation of some 3-acylchromone acetals
  作者：G.Elena Daia、Christopher D. Gabbutt、John D. Hepworth、B.Mark Heron、David E. Hibbs、Michael B. Hursthouse

  DOI：10.1016/s0040-4039(97)10733-x

  日期：1998.3

  3-Acylchromone acetals are lithiated at C-2. Subsequent electrophilic trapping gives chromones 4 together with a ring-contracted dimer 6. During the formation of some acetals, an acid-catalysed rearrangement to a 2-substituted 3-formylchromone acetal is observed.

  3-酰基色酮缩醛在C-2处被锂化。随后的亲电捕集得到色酮4以及环缩合的二聚体6。在一些缩醛的形成过程中，观察到酸催化的重排成2-取代的3-甲酰基色酮缩醛。
• Synthesis and cycloadditions of 9H-furo[3,4-b][1]benzo(thio)pyran-9-ones: furan ring formation by a novel hydrolytically induced cycloreversion
  作者：G.Elena Daia、Christopher D. Gabbutt、John D. Hepworth、B.Mark Heron、David E. Hibbs、Michael B. Hursthouse

  DOI：10.1016/s0040-4039(02)00820-1

  日期：2002.6

  C-2 lithiation of acetals 2 followed by trapping with aldehydes gives 3. Subsequent unmasking of the acetal function provides furobenzo(thio)pyrans 4, cycloadditions of which have been investigated. (C) 2002 Elsevier Science Ltd. All rights reserved.