[1-Naphthalen-2-yl-meth-(E)-ylidene]-trimethylsilanyl-amine | 220665-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1-Naphthalen-2-yl-meth-(E)-ylidene]-trimethylsilanyl-amine
• 英文别名: 1-naphthalen-2-yl-N-trimethylsilylmethanimine
• CAS: 220665-74-7
• 化学式: C₁₄H₁₇NSi
• 分子量: 227.381
• InChiKey: VTXLUMFLIOKLGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1-Naphthalen-2-yl-meth-(E)-ylidene]-trimethylsilanyl-amine 在 盐酸 、 lithium diisopropyl amide 作用下， 反应 44.0h， 生成 β-(2-naphthyl)-α,α-dimethyl-β-alanine hydrochloride
  参考文献：
  名称：

  GPIIb/IIIa Integrin Antagonists with the New Conformational Restriction Unit, Trisubstituted β-Amino Acid Derivatives, and a Substituted Benzamidine Structure

  摘要：

  Ethyl N- [3 -(2-fluoro-4-(thiazolidin-3-yl(imino)methyl)benzoyl)amino-2,2-dimethylpentanoyl]piperidine-4-acetate 40 (NSL-96184:) is a highly potent and orally active fibrinogen receptor antagonist, which is characterized by the presence of the trisubstituted beta-amino acid residue, 3 -ethyl-2,2-dimethyl-beta-alanine. This compound was developed on the basis of the SAR study of N-[3-(N-4-amidinobenzoyl)amino-2,2-dimethyl-3-phenylpropionyl]piperidine-4-acetic acid 1 (NSL-95301) with the derivatization focused on the central trisubstituted beta-amino acid unit as well as the basic amidinobenzoyl unit, and the esterification of the carboxyl group for prodrug composition, Compound 1, which was report;ed in our previous study, was discovered by the application of combinatorial chemistry. The molecular modeling study suggests that the trisubstituted beta-amino acid unit is responsible for fixing the molecule to its active conformation. Compound 40 showed an excellent profile in the in vitro and in vivo studies for its human platelet aggregation inhibitory activity and oral availability in guinea pigs. This oral availability largely depends on the modification of the amidino group with a cyclic secondary amine, i.e., thiazolidine in 40. In in vivo studies, the onset of the antiplatelet action of 40 is very fast after oral administration, whereas its duration of action is relatively short. These results suggest that 40 has an excellent therapeutic potential, especially for antithrombotic treatment in the acute phase. 3-Substituted-2,2-dimethyl-beta-amino acid residues would serve as new and useful linear templates to restrict the conformational flexibility of peptidomimetics.

  DOI：

  10.1021/jm980126v
• 作为产物：
  描述：

  sodium hexamethyldisilazane 、 2-萘甲醛 以 四氢呋喃 为溶剂， 生成 [1-Naphthalen-2-yl-meth-(E)-ylidene]-trimethylsilanyl-amine
  参考文献：
  名称：

  [3 + 2] 叔胺 N-氧化物和甲硅烷基亚胺的环加成作为 1,2-二胺的创新路线

  摘要：

  我们开发了一种一锅合成方法，通过正式的 umpolung 工艺，从易于制备且市售的前体中生产 1,2-二胺。我们的方法利用有效的[3 + 2]环加成作为以中等到高产率形成取代的1,2-二胺的关键步骤。这些产生的化合物可以进行后续的转化，证明它们作为更复杂支架的合成构件的实用性。最后，我们使用密度泛函理论模型提出了这种转变的合理机制，证明了实验观察的合理性。

  DOI：

  10.1021/acs.orglett.3c01396

文献信息

• Catalytic Enantioselective One-pot Aminoborylation of Aldehydes: A Strategy for Construction of Nonracemic α-Amino Boronates
  作者：Kai Hong、James P. Morken

  DOI：10.1021/ja402569j

  日期：2013.6.26

  We report a strategy for the conversion of aldehydes to enantiomerically enriched alpha-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B-2(pin)(2) across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl alpha-amino boronic ester derivatives.