(R)-(-)-coniceine picrate | 89772-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-(-)-coniceine picrate
• 英文别名: (-)-δ-conicein; picrate；(-)-δ-Conicein; Picrat；(8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine;2,4,6-trinitrophenol
• CAS: 89772-93-0
• 化学式: C₆H₃N₃O₇*C₈H₁₅N
• 分子量: 354.32
• InChiKey: CLOHYIHHAPWDSJ-DDWIOCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苦味酸 、 (-)-(8aR)-octahydroindolizine 以 乙醇 为溶剂， 生成 (R)-(-)-coniceine picrate
  参考文献：
  名称：

  Preparation of (R)-(+)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide: synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine

  摘要：

  We describe the transformation of (R)-(-)-1-(2'-hydroxy-1'-phenylethyl)piperidin-2-one 1 into (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide 2 using POBr3, Reduction of 2 with Red-Al at -78 degrees C gave (3R,8aR)-(-)-3-phenylbexahydro-2H-oxazolo[3,8-a]-pyridine 3 as a single diastereoisomer. The synthetic potential of these transformation is illustrated by the enantiopure synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine.

  DOI：

  10.1016/s0385-5414(07)81205-6

文献信息

• Preparation of (R)-(+)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide: synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine
  作者：A CASTRO、J RAMIREZ、J JUAREZ、J TERAN、L OREA、A GALINDO、D GNECCO

  DOI：10.1016/s0385-5414(07)81205-6

  日期：2007.12.1

  We describe the transformation of (R)-(-)-1-(2'-hydroxy-1'-phenylethyl)piperidin-2-one 1 into (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide 2 using POBr3, Reduction of 2 with Red-Al at -78 degrees C gave (3R,8aR)-(-)-3-phenylbexahydro-2H-oxazolo[3,8-a]-pyridine 3 as a single diastereoisomer. The synthetic potential of these transformation is illustrated by the enantiopure synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine.