[(2S,3S)-1-(4-甲氧基苯基)-2-苯基哌啶-3-基]甲醇 | 837364-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: [(2S,3S)-1-(4-甲氧基苯基)-2-苯基哌啶-3-基]甲醇
• 英文名称: ((2S,3S)-1-(4-methoxyphenyl)-2-phenylpiperidin-3-yl)methanol
• 英文别名: [(2S,3S)-1-(4-methoxyphenyl)-2-phenylpiperidin-3-yl]methanol
• CAS: 837364-72-4
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: IWAOGTAQRCTIKB-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以126 mg的产率得到[(2S,3S)-1-(4-甲氧基苯基)-2-苯基哌啶-3-基]甲醇
  参考文献：
  名称：

  四氢吡啶的脯氨酸-介导的对映选择性施工经由级联曼尼希型/分子内环化反应

  摘要：

  通过脯氨酸介导的级联曼尼希型/分子内环化反应，从预先形成的N -PMP（对甲氧基苯基）醛亚胺和廉价的四氢-2 H-吡喃-水溶液中进行高度非对映和对映选择性的合成2,3-二取代的四氢吡啶2,6-二醇。

  DOI：

  10.1002/adsc.200800253

文献信息

• Highly enantioselective [4+2] annulation via organocatalytic Mannich-reductive cyclization: one-pot synthesis of functionalized piperidines
  作者：Indresh Kumar、Panduga Ramaraju、Nisar A. Mir、Deepika Singh、Vivek K. Gupta、Rajnikant

  DOI：10.1039/c3cc42431f

  日期：——

  one-pot synthesis of 2,3-substituted piperidine from N-PMP aldimine and aqueous glutaraldehyde via formal [4+2] cycloaddition is reported. This reaction involves organocatalytic direct Mannich reaction-reductive cyclization with high yields (up to 90%) and excellent enantioselectivities (up to >99%). The practicability of this method is also shown at a gram scale as well as through the synthesis of functionalized

  报道了一种新的方法，可以通过正式的[4 + 2]环加成反应从N-PMP亚胺和戊二醛水溶液一锅合成2，3-取代的哌啶。该反应涉及高产率（高达90％）和优异的对映选择性（高达> 99％）的有机催化直接曼尼希反应-还原环化反应。该方法的实用性也以克为单位以及通过合成官能化的（-）-天麻碱得到了证明。
• A Mannich-Cyclization Approach for the Asymmetric Synthesis of Saturated <i>N</i>-Heterocycles
  作者：Mathias Christmann、Alexander Münch、Bianca Wendt

  DOI：10.1055/s-2004-835622

  日期：——

  A concise asymmetric synthesis of disubstituted N-heterocycles is reported. Our approach utilizes an optimized Mannich reaction of functionalized aldehydes, followed by a novel dehydrative cyclization mediated by the Staab reagent (1,1'-carbonyldiimidazole, CDI). The method was applied to the synthesis of azetidines, piperidines and pyrrolidines.

  报道了二取代 N-杂环的简明不对称合成。我们的方法利用功能化醛的优化曼尼希反应，然后是由 Staab 试剂（1,1'-羰基二咪唑，CDI）介导的新型脱水环化。该方法用于合成氮杂环丁烷、哌啶和吡咯烷。
• <i>N</i>,<i>N</i>‘-Carbonyldiimidazole-Mediated Cyclization of Amino Alcohols to Substituted Azetidines and Other <i>N</i>-Heterocycles
  作者：Renata Marcia de Figueiredo、Roland Fröhlich、Mathias Christmann

  DOI：10.1021/jo060130b

  日期：2006.5.1

  Amino alcohols are important synthons for N-heterocycles. We have developed an efficient method to activate hydroxyl groups, which avoids the use of toxic reagents and tolerates a wide variety of functional groups. Our strategy has been applied to the synthesis of functionalized p-methoxyphenyl-protected azetidines, pyrrolidines, and piperidines. The required amino alcohols were synthesized according to an optimized proline-catalyzed Mannich protocol. An azetidine analogue of ezetimibe was synthesized to demonstrate the potential for the synthesis of drug-like molecules.