9-[2-(羟甲基)苯基]-3,3-二甲基-1,5-二氧杂螺[5.5]十一烷-9-醇 | 253800-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 9-[2-(羟甲基)苯基]-3,3-二甲基-1,5-二氧杂螺[5.5]十一烷-9-醇
• 英文名称: 9-(2-hydroxymethylphenyl)-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol
• 英文别名: 9-[2-(Hydroxymethyl)phenyl]-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol
• CAS: 253800-23-6
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: LSZCXAIEBTUQAT-UHFFFAOYSA-N

物化性质

• 沸点：
  463.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-[2-(羟甲基)苯基]-3,3-二甲基-1,5-二氧杂螺[5.5]十一烷-9-醇 在 sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 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
• 作为产物：
  描述：

  2-溴苄醇 、 3,3-二甲基-1,5-二氧杂螺[5.5]十一烷-9-酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 以74.4%的产率得到9-[2-(羟甲基)苯基]-3,3-二甲基-1,5-二氧杂螺[5.5]十一烷-9-醇
  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

文献信息

• Synthesis of a Spiro[cyclohex-1,1‘-isobenzofuranyl] Dopamine Receptor Antagonist
  作者：Frank J. Urban、Bruce G. Anderson、Morgan A. Stewart、Gregory R. Young

  DOI：10.1021/op990191u

  日期：1999.11.1

  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.