(R)-1-methyl-3-(p-methoxybenzyl)-5-oxo-2,3,4,5,6,7-hexahydro-1H-azepine | 174417-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-1-methyl-3-(p-methoxybenzyl)-5-oxo-2,3,4,5,6,7-hexahydro-1H-azepine
• 英文别名: (6R)-6-[(4-methoxyphenyl)methyl]-1-methylazepan-4-one
• CAS: 174417-72-2
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: LVPOZSZHUKFRFD-CYBMUJFWSA-N

物化性质

• 沸点：
  375.4±27.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-1-methyl-3-(p-methoxybenzyl)-5-oxo-2,3,4,5,6,7-hexahydro-1H-azepine 在 PPA 、 氢溴酸 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 19.0h， 生成 氢溴酸依他佐辛; (1S,6S)-2,3,4,5,6,7-六氢-1,4-二甲基-1,6-甲桥-1H-4-苯并氮杂卓-10-醇氢溴酸盐
  参考文献：
  名称：

  Asymmetric Synthesis of (+)- and (-)-Eptazocine via an Enzymatic Reaction

  摘要：

  Starting from (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (R-(+)-4) prepared by enzymatic monoacetylation of 2-(p-methoxybenzyl)propane-1,3-diol (3) with lipase PS in the presence of vinyl acetate as an acetyl donor, lactones ((+)- and (-)-6) were obtained. Using the lactones, (+)- and (-)-eptazocine were synthesized.

  DOI：

  10.3987/com-95-7232
• 作为产物：
  描述：

  [(2R)-2-(cyanomethyl)-3-(4-methoxyphenyl)propyl] acetate 在 盐酸 、 sodium hydroxide 、 sodium hydride 、 potassium carbonate 、 sodium iodide 、 zinc(II) chloride 作用下， 以 乙醇 、 水 、 氯苯 为溶剂， 反应 63.25h， 生成 (R)-1-methyl-3-(p-methoxybenzyl)-5-oxo-2,3,4,5,6,7-hexahydro-1H-azepine
  参考文献：
  名称：

  Asymmetric Synthesis of (+)- and (-)-Eptazocine via an Enzymatic Reaction

  摘要：

  Starting from (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (R-(+)-4) prepared by enzymatic monoacetylation of 2-(p-methoxybenzyl)propane-1,3-diol (3) with lipase PS in the presence of vinyl acetate as an acetyl donor, lactones ((+)- and (-)-6) were obtained. Using the lactones, (+)- and (-)-eptazocine were synthesized.

  DOI：

  10.3987/com-95-7232

文献信息

• Asymmetric Synthesis of (+)- and (-)-Eptazocine via an Enzymatic Reaction
  作者：Shunsaku Shiotani、Hirohiko Okada、Takako Yamamoto、Kumiko Nakamata、Jun Adachi、Hiromasa Nakamoto

  DOI：10.3987/com-95-7232

  日期：——

  Starting from (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (R-(+)-4) prepared by enzymatic monoacetylation of 2-(p-methoxybenzyl)propane-1,3-diol (3) with lipase PS in the presence of vinyl acetate as an acetyl donor, lactones ((+)- and (-)-6) were obtained. Using the lactones, (+)- and (-)-eptazocine were synthesized.