2-methyl-7-octyn-2-ol | 62873-32-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-7-octyn-2-ol
• 英文别名: 2-methyl-oct-7-yn-2-ol；7-Octyn-2-ol, 2-methyl-；2-methyloct-7-yn-2-ol
• CAS: 62873-32-9
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: KAFGPFJIXYZFNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-7-octyn-2-ol 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 重铬酸吡啶 、 正丁基锂 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 二乙胺 为溶剂， 反应 79.0h， 生成 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-dihomo-21-norvitamin D₃ triisopropylsilyl ether
  参考文献：
  名称：

  Novel 1α,25-Dihydroxyvitamin D₃ Analogues with the Side Chain at C12

  摘要：

  The plethora of actions of 1 alpha,25(OH)(2)D-3 in various systems suggested wide clinical applications of vitamin D nuclear receptor (VDR) ligands in treatments of inflammation, dermatological indication, osteoporosis, cancers, and autoimmune diseases. More than 3000 vitamin D analogues have been synthesized in order to reduce the calcemic side effects while maintaining the transactivation potency of the natural ligand. In light of the crystal structures of the vitamin D nuclear receptor (VDR), novel analogues of the hormone 1 alpha,25(OH)2D3 with side chains attached to C-12 were synthesized via the convergent Wittig-Horner approach. Among the compounds studied, the analogue 2b showed the highest binding affinity for VDR and was the most potent at inducing VDR transcriptional activity in a transient transfection assay (20% of the transactivation activity of the natural ligand).

  DOI：

  10.1021/jm049016g
• 作为产物：
  描述：

  2-methyl-3-octyn-2-ol 在 propane-1,3-diamine potassium salt 作用下， 生成 2-methyl-7-octyn-2-ol
  参考文献：
  名称：

  炔醇与3-氨基丙基酰胺钾的极易异构化。一种新的高产率合成功能分化的αω-双官能结构

  摘要：

  3-氨基丙酰胺钾很容易从KH和3-氨基丙胺中就地制备，可在0至数分钟内在几分钟之内迅速将丙-2-炔醇和其他炔醇中的三键快速多位异构化至远离羟基官能团的链末端20°C。

  DOI：

  10.1039/c39760000959

文献信息

• Exceptionally easy isomerization of acetylenic alcohols with potassium 3-aminopropylamide. A new, high yield synthesis of functionally differentiated αω-difunctional structures
  作者：Charles Allan Brown、A. Yamashita

  DOI：10.1039/c39760000959

  日期：——

  Potassium 3-aminopropylamide, readily prepared in situ from KH and 3-aminopropylamine, effects rapid, multipositional isomerization of the triple bond in prop-2-ynylic and other acetylenic alcohols to the chain terminus remote from the hydroxy function, within minutes at 0–20 °C.

  3-氨基丙酰胺钾很容易从KH和3-氨基丙胺中就地制备，可在0至数分钟内在几分钟之内迅速将丙-2-炔醇和其他炔醇中的三键快速多位异构化至远离羟基官能团的链末端20°C。
• Synthesis and Biological Evaluation of 1α,25-Dihydroxyvitamin D₃ Analogues with a Long Side Chain at C12 and Short C17 Side Chains
  作者：Diego M. Carballa、Samuel Seoane、Flavia Zacconi、Xenxo Pérez、Antonio Rumbo、Silvia Alvarez-Díaz、María Jesús Larriba、Román Pérez-Fernández、Alberto Muñoz、Miguel Maestro、Antonio Mouriño、Mercedes Torneiro

  DOI：10.1021/jm3008272

  日期：2012.10.25

  cyclization–Suzuki coupling method. The new analogues were assayed against human colon and breast cancer cell lines and in mice. All new vitamin D3 analogues bound less strongly to the VDR than 1α,25-dihydroxyvitamin D3 but had similar antiproliferative, pro-differentiating, and transcriptional activity as the native hormone. In vivo, the three analogues had markedly low calcemic effects.

  结构导向的优化用于设计新的1α，25-二羟基维生素D 3的类似物，其在C12处带有主侧链，在C17处具有较短的第二条羟基化链。新化合物5a – c是从酮9（可以很容易地从Inhoffen–Lythgoe二醇中获得）有效合成的，5a，5b和5c的总收率分别为15％，6％和3％。通过Pd催化串联环化-Suzuki偶联方法引入了三烯体系。测定了针对人结肠和乳腺癌细胞系以及小鼠中的新类似物。所有新的维生素D 3类似物与VDR的结合强度不如1α，25-二羟基维生素D 3，但具有与天然激素相似的抗增殖，促分化和转录活性。在体内，这三种类似物的钙化作用明显降低。
• Novel 1α,25-Dihydroxyvitamin D₃ Analogues with the Side Chain at C12
  作者：Xosé C. González-Avión、Antonio Mouriño、Natacha Rochel、Dino Moras

  DOI：10.1021/jm049016g

  日期：2006.3.1

  The plethora of actions of 1 alpha,25(OH)(2)D-3 in various systems suggested wide clinical applications of vitamin D nuclear receptor (VDR) ligands in treatments of inflammation, dermatological indication, osteoporosis, cancers, and autoimmune diseases. More than 3000 vitamin D analogues have been synthesized in order to reduce the calcemic side effects while maintaining the transactivation potency of the natural ligand. In light of the crystal structures of the vitamin D nuclear receptor (VDR), novel analogues of the hormone 1 alpha,25(OH)2D3 with side chains attached to C-12 were synthesized via the convergent Wittig-Horner approach. Among the compounds studied, the analogue 2b showed the highest binding affinity for VDR and was the most potent at inducing VDR transcriptional activity in a transient transfection assay (20% of the transactivation activity of the natural ligand).