(R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ylium bromide | 1001200-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ylium bromide
• 英文别名: (3R)-3-phenyl-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridin-4-ium;bromide
• CAS: 1001200-66-3
• 化学式: Br*C₁₃H₁₆NO
• 分子量: 282.18
• InChiKey: DJJLXCXNTFZRCS-YDALLXLXSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ylium bromide 在 红铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.25h， 以100%的产率得到3-phenylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridine
  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
• 作为产物：
  描述：

  (αR)-N-(2-hydroxy-1-phenylethyl)piperidine-2-one 在 三溴氧磷 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以100%的产率得到(R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ylium bromide
  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.