4-(tert-butyl)phenyl(pyridin-3-yl)methanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(tert-butyl)phenyl(pyridin-3-yl)methanol
• 英文别名: (4-Tert-butylphenyl)-pyridin-3-ylmethanol
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: IIUOUPDUGQBPII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸异丙烯酯 、 4-(tert-butyl)phenyl(pyridin-3-yl)methanol 在 lipoprotein lipase-D₁ 、 C₄₃H₃₅ClO₁₀Ru 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 96.5h， 以76%的产率得到(S)-(4-(tert-butyl)phenyl)(pyridin-3-yl)methyl acetate
  参考文献：
  名称：

  Dynamic Kinetic Resolution of Diarylmethanols with an Activated Lipoprotein Lipase

  摘要：

  We explored the kinetic resolution of 31 different diarylmethanols with an activated lipoprotein lipase (LPL-D1) which was about 3000-fold more active than its native counterpart in organic solvent. Most of the substrates tested were accepted by LPL-D1 with good to high enantioselectivity in the kinetic resolution. Next, we explored the dynamic kinetic resolutions (DKRs) of these substrates (24 out of 31) using LPL-D1 and a ruthenium-based racemization catalyst in combination, which provided satisfactory yields (71-96%) and high enantiopurities (90-99% cc). As an illustrative example for the synthetic applications of the DKR procedure, we synthesized L-cloperastine, an antitussive drug, from phenyl-(p-trimethylsilylphenyl)methanol via DKR.

  DOI：

  10.1021/cs501629m
• 作为产物：
  描述：

  4-叔丁基溴苯 、 3-{[(三甲基硅烷基)氧基]甲基}吡啶 在 palladium diacetate 、 lithium hexamethyldisilazane 、 4,6-二(二苯基膦)吩嗪 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 24.33h， 以66%的产率得到4-(tert-butyl)phenyl(pyridin-3-yl)methanol
  参考文献：
  名称：

  钯催化吡啶甲基甲硅烷基醚的苄基芳基化：一锅法合成芳基（吡啶基）甲醇

  摘要：

  描述了吡啶基甲基甲硅烷基醚与芳基溴的有效钯催化直接芳基化反应。基于Pd(OAc) 2 /NIXANTPHOS 的催化剂以良好至优异的收率提供芳基（吡啶基）甲醇衍生物（33 个示例，收率 57–100%）。该方案与不同的甲硅烷基醚保护基团兼容，可在有效的一锅法中提供受保护的醇或游离的醇。证明了反应的可扩展性。

  DOI：

  10.1021/acs.orglett.6b00450

文献信息

• Dynamic Kinetic Resolution of Diarylmethanols with an Activated Lipoprotein Lipase
  作者：Jusuk Lee、Yeonock Oh、Yoon Kyung Choi、Eunjeong Choi、Kyungwoo Kim、Jaiwook Park、Mahn-Joo Kim

  DOI：10.1021/cs501629m

  日期：2015.2.6

  We explored the kinetic resolution of 31 different diarylmethanols with an activated lipoprotein lipase (LPL-D1) which was about 3000-fold more active than its native counterpart in organic solvent. Most of the substrates tested were accepted by LPL-D1 with good to high enantioselectivity in the kinetic resolution. Next, we explored the dynamic kinetic resolutions (DKRs) of these substrates (24 out of 31) using LPL-D1 and a ruthenium-based racemization catalyst in combination, which provided satisfactory yields (71-96%) and high enantiopurities (90-99% cc). As an illustrative example for the synthetic applications of the DKR procedure, we synthesized L-cloperastine, an antitussive drug, from phenyl-(p-trimethylsilylphenyl)methanol via DKR.
• Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols
  作者：Alexandra R. Rivero、Byeong-Seon Kim、Patrick J. Walsh

  DOI：10.1021/acs.orglett.6b00450

  日期：2016.4.1

  An efficient palladium-catalyzed direct arylation of pyridylmethyl silyl ethers with aryl bromides is described. A Pd(OAc)2/NIXANTPHOS-based catalyst provides aryl(pyridyl)methyl alcohol derivatives in good to excellent yields (33 examples, 57–100% yield). This protocol is compatible with different silyl ether protecting groups, affording either the protected or the free alcohols in an effective one-pot

  描述了吡啶基甲基甲硅烷基醚与芳基溴的有效钯催化直接芳基化反应。基于Pd(OAc) 2 /NIXANTPHOS 的催化剂以良好至优异的收率提供芳基（吡啶基）甲醇衍生物（33 个示例，收率 57–100%）。该方案与不同的甲硅烷基醚保护基团兼容，可在有效的一锅法中提供受保护的醇或游离的醇。证明了反应的可扩展性。