(2S)-3-methyl-N-((S)-1-phenylethyl)butan-2-amine | 25102-89-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-3-methyl-N-((S)-1-phenylethyl)butan-2-amine
• 英文别名: (2S)-3-methyl-N((S)-1-phenylethyl)butan-2-amine；SS-(S)-1,2-dimethylpropylidene(1-phenylethyl)amine；Dimethyl-1,2-propyl-phenylaethyl-amin；Dimethyl-1,2-propyl-phenylaethylamin；(2S)-3-methyl-N-[(1S)-1-phenylethyl]butan-2-amine
• CAS: 25102-89-0
• 化学式: C₁₃H₂₁N
• 分子量: 191.316
• InChiKey: ZMZIQRWISWNDFB-RYUDHWBXSA-N

物化性质

• 沸点：
  249.4±9.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (S)-1,2-dimethylpropylidene(1-phenylethyl)amine 在 passivated Cu/Ni/Mo (13/40/1)/ZrO₂ 氢气 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、10.0 MPa 条件下， 以92%的产率得到
  参考文献：
  名称：

  PROCESS FOR DIASTEREOSELECTIVE CONVERSION OF CHIRAL IMINES

  摘要：

  对式I的手性亚胺进行不对映选择性转化，生成式II的胺，其中R1到R4基团如描述中所定义，且R1和R2不同，通过在氢气和含铜杂质催化剂的存在下将式I的亚胺转化。

  公开号：

  US20100274053A1

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%） .
• 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.
• Charles,J.-P. et al., Bulletin de la Societe Chimique de France, 1970, p. 4439 - 4446
  作者：Charles,J.-P. et al.

  DOI：——

  日期：——
• PROCESS FOR DIASTEREOSELECTIVE CONVERSION OF CHIRAL IMINES
  申请人：Siegel Wolfgang

  公开号：US20100274053A1

  公开（公告）日：2010-10-28

  Diastereoselective conversion of chiral imines of the formula I to amines of the formula II where the R 1 to R 4 radicals are each as defined in the description and R 1 and R 2 are different than one another, by converting the imine of the formula I in the presence of hydrogen and a heterogeneous copper-containing catalyst.

  对式I的手性亚胺进行不对映选择性转化，生成式II的胺，其中R1到R4基团如描述中所定义，且R1和R2不同，通过在氢气和含铜杂质催化剂的存在下将式I的亚胺转化。