1-[(2S,4S,5S)-5-methyl-2-phenyl-1,3-dioxan-4-yl]-1-propanone | 501084-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 1-[(2S,4S,5S)-5-methyl-2-phenyl-1,3-dioxan-4-yl]-1-propanone
• 英文别名: 1-[(2S,4S,5S)-5-methyl-2-phenyl-1,3-dioxan-4-yl]propan-1-one
• CAS: 501084-25-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: XZOIYIIMNRJWCW-BPNCWPANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(2S,4S,5S)-5-methyl-2-phenyl-1,3-dioxan-4-yl]-1-propanone 在 氯代二环己基硼烷 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 Petroleum ether 为溶剂， 反应 53.0h， 生成 (1R,2R,3S)-2-methyl-1-[(2R,4R,5R)-5-methyl-2-phenyl-1,3-dioxan-4-yl]-1-[(2S,4S,5S)-5-methyl-2-phenyl-1,3-dioxan-4-yl]propane-1,3-diol
  参考文献：
  名称：

  Synthesis and Conformational Analysis of meso-Ter(1,3-dioxan-4-yls)

  摘要：

  A convergent synthesis of the meso-ter(1,3-dioxanyls) 8-11 has been achieved, starting from two enantiomeric building blocks in each case. The stereogenic centres in the central linkage region were set up by stereocontrolled aldol additions. Structure assignment of the final products was based on comparisons between experimental and calculated (3)J(H,H) coupling constants, which reflect distinct conformer populations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3455::aid-ejoc3455>3.0.co;2-v
• 作为产物：
  描述：

  ((2S,4S,5S)-5-methyl-2-phenyl-1,3-dioxan-4-yl)methanol 在 吡啶 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-[(2S,4S,5S)-5-methyl-2-phenyl-1,3-dioxan-4-yl]-1-propanone
  参考文献：
  名称：

  Synthesis and Conformational Analysis of meso-Ter(1,3-dioxan-4-yls)

  摘要：

  A convergent synthesis of the meso-ter(1,3-dioxanyls) 8-11 has been achieved, starting from two enantiomeric building blocks in each case. The stereogenic centres in the central linkage region were set up by stereocontrolled aldol additions. Structure assignment of the final products was based on comparisons between experimental and calculated (3)J(H,H) coupling constants, which reflect distinct conformer populations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200210)2002:20<3455::aid-ejoc3455>3.0.co;2-v

文献信息

• Synthesis and Conformational Analysis of meso-Ter(1,3-dioxan-4-yls)
  作者：Reinhard W. Hoffmann、Gemma Mas、Trixi Brandl

  DOI：10.1002/1099-0690(200210)2002:20<3455::aid-ejoc3455>3.0.co;2-v

  日期：2002.10

  A convergent synthesis of the meso-ter(1,3-dioxanyls) 8-11 has been achieved, starting from two enantiomeric building blocks in each case. The stereogenic centres in the central linkage region were set up by stereocontrolled aldol additions. Structure assignment of the final products was based on comparisons between experimental and calculated (3)J(H,H) coupling constants, which reflect distinct conformer populations. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.