3-[6-[2-(2-hydroxyethyl)phenyl]-1,3-benzodioxol-5-yl]-N-[(1S)-1-phenylethyl]propanamide | 791814-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-[6-[2-(2-hydroxyethyl)phenyl]-1,3-benzodioxol-5-yl]-N-[(1S)-1-phenylethyl]propanamide
• CAS: 791814-77-2
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: KOXIORGQEXHGFJ-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[6-[2-(2-hydroxyethyl)phenyl]-1,3-benzodioxol-5-yl]-N-[(1S)-1-phenylethyl]propanamide 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 72.5h， 生成 17,19-Dioxa-10-azatetracyclo[12.7.0.02,7.016,20]henicosa-1(21),2,4,6,14,16(20)-hexaene
  参考文献：
  名称：

  Synthesis of the Enantiomers of Hexahydrodibenz[d,f]azecines

  摘要：

  Suzuki coupling procedures were used to make appropriate 2-(3-aminopropyl)- 2'-(2-mesyloxy)ethyl disubstituted biphenyl derivatives 19 and 20 from which the racemic hexahydrodibenz[d,f]azecines 3 and 4 were produced following intramolecular mesyloxy displacement in dilute solution. The enantiomers of the former azecine were prepared by use of an analogue of the biphenyl aminomesylate 19 having a chiral auxiliary bound to the amino group during the closure of the 10-membered ring. Absolute configurations were assigned by X-ray diffraction analysis of compound 28.

  DOI：

  10.1021/jo049157q
• 作为产物：
  描述：

  6-溴-3,4-亚甲基二氧苯甲醛 在 palladium on activated charcoal palladium diacetate 、 sodium hydroxide 、 氢气 、 碳酸氢钠 、 四已基碘化铵 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-[6-[2-(2-hydroxyethyl)phenyl]-1,3-benzodioxol-5-yl]-N-[(1S)-1-phenylethyl]propanamide
  参考文献：
  名称：

  Synthesis of the Enantiomers of Hexahydrodibenz[d,f]azecines

  摘要：

  Suzuki coupling procedures were used to make appropriate 2-(3-aminopropyl)- 2'-(2-mesyloxy)ethyl disubstituted biphenyl derivatives 19 and 20 from which the racemic hexahydrodibenz[d,f]azecines 3 and 4 were produced following intramolecular mesyloxy displacement in dilute solution. The enantiomers of the former azecine were prepared by use of an analogue of the biphenyl aminomesylate 19 having a chiral auxiliary bound to the amino group during the closure of the 10-membered ring. Absolute configurations were assigned by X-ray diffraction analysis of compound 28.

  DOI：

  10.1021/jo049157q