N,N-Diisopropyl-2-((S)-1-methyl-but-3-enyl)-benzamide | 159888-25-2

• 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: N,N-Diisopropyl-2-((S)-1-methyl-but-3-enyl)-benzamide
• 英文别名: Benzamide, 2-[(1S)-1-methyl-3-butenyl]-N,N-bis(1-methylethyl)-；2-[(2S)-pent-4-en-2-yl]-N,N-di(propan-2-yl)benzamide
• CAS: 159888-25-2
• 化学式: C₁₈H₂₇NO
• 分子量: 273.418
• InChiKey: PNEYBYDCSQEUOF-HNNXBMFYSA-N

物化性质

• 沸点：
  384.7±21.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氯甲烷 、 在 仲丁基锂 、 鹰爪豆碱 作用下， 生成 N,N-Diisopropyl-2-((R)-1-methyl-but-3-enyl)-benzamide 、 N,N-Diisopropyl-2-((S)-1-methyl-but-3-enyl)-benzamide
  参考文献：
  名称：

  Asymmetric Substitutions: High and Opposite Enantioselective Alkylations of a Racemic Organolithium Intermediate in the Presence of (-)-Sparteine

  摘要：

  DOI：

  10.1021/ja00100a053

文献信息

• Two Different Pathways of Stereoinformation Transfer:  Asymmetric Substitutions in the (−)-Sparteine Mediated Reactions of Laterally Lithiated <i>N,N</i><i>-</i>Diisopropyl-<i>o</i>-ethylbenzamide and <i>N</i>-Pivaloyl-<i>o</i>-ethylaniline
  作者：S. Thayumanavan、Amit Basu、Peter Beak

  DOI：10.1021/ja970930r

  日期：1997.9.1

  Highly enantioenriched substitution products can be obtained by the (−)-sparteine mediated lithiation−substitution reactions of the laterally lithiated intermediates 3·1 and 14·1 derived from the amides 2 and 13. Either enantiomer of the products can be obtained with high enantioenrichment using (−)-sparteine as the ligand by appropriate choice of the protocol. The enantiodetermining step in both sequences

  由酰胺2和13衍生的横向锂化中间体3·1和14·1的(-)-sparteine介导的锂化-取代反应可以获得高度对映体富集的取代产物。产物的任一对映体都可以通过高对映体富集获得using (−)-sparteine as the ligand by appropriate choice of the protocol. 两个序列中的对映体决定步骤发生在去质子化之后。3·1 序列中的对映体富集来自动态动力学分辨率，而 14·1 序列中的对映体富集来自动态热力学分辨率。
• Conformational Control of Flexible Molecules:  Design and Synthesis of Novel Chiral 1,5-Diaza-<i>cis</i>-decalins
  作者：Zhenrong Xu、Marisa C. Kozlowski

  DOI：10.1021/jo025503x

  日期：2002.5.1

  Control of the conformational equilibria of 1,5-diaza-cis-decalins, a new class of chiral diamine ligands, has been investigated. Chiral 2,6- and 3,7-substituted derivatives of 1,5-diaza-cis-decalins were designed to stabilize the conformational form needed to chelate a lithium. These derivatives were synthesized in optically pure form starting from 1,5-diaza-cis-decalin. Due to the rigid and conformationally well-defined nature of these compounds, the potential of these compounds as chiral diamine ligands was investigated. Asymmetric lithiation-substitution reactions of N-Boc-pyrrolidine and N,N-diisopropyl-o-ethylbenzamide were performed using these ligands and up to 60% ee was obtained. For the latter substrate, results spanning a range from 32% ee (R) to 60% ee (S) were obtained (Deltaee = 92%) with 1,5-diaza-cis-decalin ligands differing only in the location of two methyl substituents. Unlike many other diamines that have been employed in asymmetric lithiation-substitution reactions, the limited conformational flexibility of the 1,5-diaza-cis-decalins is analogous to (-)-sparteine such that these results may permit the construction of structure-activity relationships.