(2S)-N-((S)-1-phenylethyl)octan-2-amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-N-((S)-1-phenylethyl)octan-2-amine
• 英文别名: (3S)-N((S)-1-phenylethyl)octan-5-amine；(2S)-N-[(1S)-1-phenylethyl]octan-2-amine
• 化学式: C₁₆H₂₇N
• 分子量: 233.397
• InChiKey: JOIDDIOTZMVSHC-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  ((E)-1-methylheptylidene)((S)-1-phenylethyl)amine 以83%的产率得到
  参考文献：
  名称：

  Fuller Joseph C., Belisle Christopher M., Goralski Christian T., Singaram+, Tetrahedron Lett, 35 (1994) N 30, S 5389- 5392

  摘要：

  DOI：

文献信息

• A One-Pot Asymmetric Sequential Amination-Alkylation of Aldehydes: Expedient Synthesis of Aliphatic Chiral Amines
  作者：Vijay N. Wakchaure、Rashmi R. Mohanty、Ahson J. Shaikh、Thomas C. Nugent

  DOI：10.1002/ejoc.200600781

  日期：2007.2

  asymmetric sequential amination-alkylation method has been developed for the synthesis of alkyl-alkyl′ α-chiral primary amines (aliphatic primary amines with a chiral center adjacent to the nitrogen atom) from aldehydes. In situ aldimine formation from non-branched, α-branched, and β-branched aliphatic aldehydes with (R)- or (S)-α-(methylbenzyl)amine [catalyzed by 5 mol-% Ti(OiPr)4] followed by reaction

  已经开发了一种一锅不对称顺序胺化-烷基化方法，用于从醛合成烷基-烷基'α-手性伯胺（手性中心与氮原子相邻的脂肪族伯胺）。由非支化、α-支化和 β-支化脂肪醛与 (R)- 或 (S)-α-（甲基苄基）胺 [由 5 mol-% Ti(OiPr)4 催化] 原位形成醛亚胺在三氟化硼或烯丙基格氏试剂存在下与甲基、乙基或正丁基铜酸铜络合物反应为胺 2 或 5 提供了良好的产率 (77–88%) 和非对映体过量 (77–92%)。为了证明该方法的有效性，一些仲胺产物（2d、2e 和 5）被氢解，得到相应的对映体富集的烷基-烷基'α-手性伯胺 3d、3e 和 6（产率 86-96%） .
• Step-Efficient Access to Chiral Primary Amines
  作者：Thomas Nugent、Sofiya Marinova

  DOI：10.1055/s-0032-1317589

  日期：——

  Routes to enantioenriched amines are outlined that employ reductive amination and carbanion addition methods. The strategies require either one or two reaction steps from prochiral carbonyl compounds for the synthesis of the corresponding chiral primary amines.
• Ytterbium Acetate Promoted Asymmetric Reductive Amination:  Significantly Enhanced Stereoselectivity
  作者：Thomas C. Nugent、Mohamed El-Shazly、Vijay N. Wakchaure

  DOI：10.1021/jo7021235

  日期：2008.2.1

  Reductive amination of prochiral unhindered 2-alkanones 1 with (R)- or (S)-alpha-MBA in the presence of Yb(OAc)(3) (50-110 mol %), Raney-Ni, and hydrogen (120 psi) results in increased diastereoselectivity for the amine products 2 (80-89% de) with good yield (80-87%). The increased de is based on comparison with the best previously reported de's when using (R)- or (S)-alpha-MBA, regardless of the strategy employed [stepwise (isolation of ketimines) or one-pot (reductive amination)], reducing agent examined, or achiral Lewis acid or Bronsted acid examined. An in situ cis- to trans-ketimine isomerization mechanism, promoted by Yb(OAC)(3), has been proposed to account for the observed increase in diastereoselectivity and suggests a new entry into the control of ketimine geometry.
• WO2007/104357
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/104359
  申请人：——

  公开号：——

  公开（公告）日：——