erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine | 116836-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine
• 英文别名: erythro-N-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine；(2S,3S)-3-hydroxy-2-methyl-3-phenyl-1-piperidin-1-ylpropan-1-one
• CAS: 116836-46-5；99114-35-9；99114-36-0；116596-04-4
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: QPDPZOMKMRLXCH-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以81%的产率得到erythro-N-(3-hydroxy-2-methyl-3-phenylpropyl)piperidine
  参考文献：
  名称：

  Erythro-directive reduction of .alpha.-substituted alkanones by means of hydrosilanes in acidic media

  摘要：

  DOI：

  10.1021/jo00258a004
• 作为产物：
  描述：

  N,N-五亚甲基丙酰胺 在 正丁基锂 、 二甲基苯基硅烷 、 二异丙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.58h， 生成 erythro-1-(3-hydroxy-2-methyl-3-phenylpropanoyl)piperidine
  参考文献：
  名称：

  erythro-DIRECTED REDUCTION OF A b-KETO AMIDE: ERYTHRO-1-(3-HYDROXY-2-METHYL-3-PHENYLPROPANOYL)PIPERIDINE

  摘要：

  DOI：

  10.15227/orgsyn.069.0044

文献信息

• Highly stereoselective reduction of .alpha.-substituted .beta.-keto amides by means of hydrosilane-fluoride ion and hydrosilane-acid reagent. A practical approach to aldols of both threo and erythro configurations
  作者：Makoto Fujita、Tamejiro Hiyama

  DOI：10.1021/ja00312a098

  日期：1985.12
• Enolboration. 7. Dicyclohexyliodoborane, a Highly Stereoselective Reagent for the Enolboration of Tertiary Amides. Effects of Solvent and Aldolization Temperature on Stereochemistry in Achieving the Stereoelective Synthesis of either Syn or Anti Aldols
  作者：Kumaraperumal Ganesan、Herbert C. Brown

  DOI：10.1021/jo00103a028

  日期：1994.12

  A highly stereoselective enolboration of tertiary amides has been,accomplished for the first time with dicyclohexyliodoborane, Chx(2)BI. A systematic study of the enolboration of representative N,N-dialkylpropionamides (CH(3)CH(2)CONR'(2)) with Chx(2)BI in the presence of various tertiary amines of variable steric requirements revealed an unusual aldol stereoselectivity in different solvents and at different aldolization temperatures. Both the nature of solvent and the aldolization temperature influence the stereochemistry of enolboration, with the solvent effect being greater than that of the temperature. Aliphatic and alicyclic hydrocarbon solvents favor formation of the syn aldols from the enol borinates by aldolization at lower temperature (-78 degrees C), whereas most of the other solvents examined, such as aromatic and chlorinated aliphatic solvents, favor formation of the anti aldols by aldolization at relatively higher temperatures (0 or 25 degrees C). The remarkable effects of both temperature and solvent in the case of tertiary amides raise a question about the validity of the previously assumed constancy of the Z to syn and E to anti relationship, suggesting either a possible isomerization of enol borinates with temperature or a different aldolization transition state with different solvent. While the effect of steric requirements of the dialkylamino group of the tertiary amide does not contribute significantly to the stereochemistry, that of the amine exerts a considerable influence. The present study establishes a simple procedure for the stereoselective synthesis of either syn or anti aldols from representative tertiary amides merely by changing the : solvent and the aldolization temperature.