(2R,3R)-3-hydroxy-N,N-dimethyl-2,3-diphenylpropanamide | 18181-05-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R,3R)-3-hydroxy-N,N-dimethyl-2,3-diphenylpropanamide
• CAS: 18181-05-0；72540-94-4；72540-95-5
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: YASXXCJZHWCDQW-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  (2R,3R)-3-hydroxy-N,N-dimethyl-2,3-diphenylpropanamide 生成 [(1R,2R)-3-(dimethylamino)-3-oxo-1,2-diphenylpropyl] acetate
  参考文献：
  名称：

  MLADENOVA M.; BLAGOEV B.; KURTEV B., BULL. SOC. CHIM. FRANCE, 1979, PART 2, NO 1-2, 77-80

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 、 N,N-二甲基-2-苯基乙酰胺 生成 3-hydroxy-N,N-dimethyl-2,3-diphenylpropanamide 、 (2R,3R)-3-hydroxy-N,N-dimethyl-2,3-diphenylpropanamide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00103a028

文献信息

• Manganese‐Catalyzed <i>anti</i> ‐Selective Asymmetric Hydrogenation of α‐Substituted β‐Ketoamides
  作者：Linli Zhang、Zheng Wang、Zhaobin Han、Kuiling Ding

  DOI：10.1002/anie.202006383

  日期：2020.9

  A Mn‐catalyzed diastereo‐ and enantioselective hydrogenation of α‐substituted β‐ketoamides has been realized for the first time under dynamic kinetic resolution conditions. anti‐α‐Substituted β‐hydroxy amides, which are useful building blocks for the synthesis of bioactive molecules and chiral drugs, were prepared in high yields with excellent selectivity (up to >99 % dr and >99 % ee) and unprecedentedly

  在动态动力学拆分条件下，首次实现了Mn催化的α-取代的β-酮酰胺的非对映和对映选择性氢化。抗-α-取代的β-羟基酰胺是生物活性分子和手性药物合成的有用组成部分，以高收率，高选择性（高达> 99％dr和> 99％ee）和前所未有的高活性制备。（TON最高10000）。出色的立体选择性的起源已通过DFT计算得以阐明。
• Sur les organometalliques issus de thioamides
  作者：Claude Goasdoue、Nicole Goasdoue、Marcel Gaudemar、Margarita Mladenova

  DOI：10.1016/s0022-328x(00)86714-5

  日期：1981.3

  Organometallic compounds derived from thioamides RCH2CSN(R3)2 condense normally with aldehydes and saturated ketones. Condensation with 4-t-butyl-cyclohexanone leads predominantly to equatorial attack by the organometallic compound. These results suggest that the organometallic structure as RCHC(SM)N(R3)2.

  衍生自硫酰胺RCH 2 CSN（R 3）2的有机金属化合物通常与醛和饱和酮缩合。与4-叔丁基-环己酮的缩合主要导致有机金属化合物发生赤道侵蚀。这些结果表明有机金属结构为RCHC（SM）N（R 3）2。