1-(3'H-spiro[cyclohex-1,1'-isobenzofuran]-(trans)-4-yl)piperazine | 253800-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1-(3'H-spiro[cyclohex-1,1'-isobenzofuran]-(trans)-4-yl)piperazine
• CAS: 253800-27-0
• 化学式: C₁₇H₂₄N₂O
• 分子量: 272.39
• InChiKey: DXEXVQNACIYPAT-JCNLHEQBSA-N

物化性质

• 沸点：
  422.4±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  24.5
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(3'H-spiro[cyclohex-1,1'-isobenzofuran]-(trans)-4-yl)piperazine 、 2,4-二氟苯腈 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以66%的产率得到2-fluoro-4-(trans)-(4-(3'H-spiro[cyclohex-1,1'-isobenzofuran]-4-yl)piperazin-1-yl)benzonitrile
  参考文献：
  名称：

  Synthesis of a Spiro[cyclohex-1,1‘-isobenzofuranyl] Dopamine Receptor Antagonist

  摘要：

  Two syntheses of the novel CNS agent, 2-fluoro-4-(trans)-(4-(3'H-spiro[cyclohex-1,1'-isobenzofuran]-4-yl)-piperazin-1-yl)- benzonitrile, 1, are presented. The first relied on a reductive alkylation with low regionselectivity (I:1) hut was sufficient for the preparation of kilogram quantities, The second used a selective ketone reduction of 3'H-spiro[cyclohexane-1,1'-isobenzofuran]-4-one 8, with sodium borohydride to provide the cis-alcohol, 3'H-spiro[cyclohexane-1,1'-isobenzofuran]-(cis)-4-ol,11. A simple process for the conversion of 11 to 1 is described, Regioselective reactions with 2,4-difluorobenzonitrile under mild conditions are described.

  DOI：

  10.1021/op990191u
• 作为产物：
  描述：

  3'H-spiro[cyclohexane-1,1'-isobenzofuran]-4-one 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 29.0h， 生成 1-(3'H-spiro[cyclohex-1,1'-isobenzofuran]-(trans)-4-yl)piperazine
  参考文献：
  名称：

  Synthesis of a Spiro[cyclohex-1,1‘-isobenzofuranyl] Dopamine Receptor Antagonist

  摘要：

  Two syntheses of the novel CNS agent, 2-fluoro-4-(trans)-(4-(3'H-spiro[cyclohex-1,1'-isobenzofuran]-4-yl)-piperazin-1-yl)- benzonitrile, 1, are presented. The first relied on a reductive alkylation with low regionselectivity (I:1) hut was sufficient for the preparation of kilogram quantities, The second used a selective ketone reduction of 3'H-spiro[cyclohexane-1,1'-isobenzofuran]-4-one 8, with sodium borohydride to provide the cis-alcohol, 3'H-spiro[cyclohexane-1,1'-isobenzofuran]-(cis)-4-ol,11. A simple process for the conversion of 11 to 1 is described, Regioselective reactions with 2,4-difluorobenzonitrile under mild conditions are described.

  DOI：

  10.1021/op990191u