(1S,2S)-2-(dibenzylamino)-3-methyl-1-phenylbutan-1-ol | 111060-98-1

• 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: (1S,2S)-2-(dibenzylamino)-3-methyl-1-phenylbutan-1-ol
• CAS: 111060-98-1
• 化学式: C₂₅H₂₉NO
• 分子量: 359.511
• InChiKey: FOCSUXTYTYXWLA-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-(dibenzylamino)-3-methyl-1-phenylbutan-1-ol 在 氯化亚砜 、 10 wt% Pd(OH)2 on carbon 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 90.0h， 生成 (1S,2S)-15N-(1-(benzylamino)-1-phenyl-3-methylbutan-2-yl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds

  摘要：

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.079
• 作为产物：
  描述：

  (S)-benzyl 2-(dibenzylamino)-3-methylbutanoate 在 lithium aluminium tetrahydride 、 草酰氯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.75h， 生成 (1S,2S)-2-(dibenzylamino)-3-methyl-1-phenylbutan-1-ol
  参考文献：
  名称：

  Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds

  摘要：

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.079

文献信息

• Stereoselective Arylation of Amino Aldehydes: Overriding Natural Substrate Control through Chelation
  作者：Bruna S. Martins、Angélica V. Moro、Diogo S. Lüdtke

  DOI：10.1021/acs.joc.7b00215

  日期：2017.3.17

  reaction of chiral, enantiopure acyclic α-amino aldehydes enabled by a B/Zn exchange reaction between arylboronic acids and Et2Zn is reported. The presence of dibenzyl substituents at the nitrogen plays a key role in the stereochemical outcome of the reaction, and chelation is favored over the natural tendency of this type of substrate to undergo Felkin–Anh controlled additions with organomagnesium and organolithium

  报道了通过芳基硼酸和Et 2 Zn之间的B / Zn交换反应实现的手性，对映体纯的无环α-氨基醛的螯合控制的芳基化反应。氮上存在的二苄基取代基在反应的立体化学结果中起关键作用，螯合作用优于这种类型的底物通过有机镁和有机锂试剂进行费金-安赫控制的加成反应的自然趋势。
• New β-amino thiols as efficient catalysts for highly enantioselective alkenylzinc addition to aldehydes
  作者：Shi-Liang Tseng、Teng-Kuei Yang

  DOI：10.1016/j.tetasy.2004.11.093

  日期：2005.2

  A series of new optically active beta-amino thiols and thiolacetates prepared from the simple natural amino acid, (S)-(-)-valine, were found to be effective catalysts for the enantioselective addition of alkenylzinc to alclehydes and thereby providing an efficient route for chiral (E)-allylic alcohols with ees of up to >99% in the presence of 7a (1 mol %). (C) 2005 Published by Elsevier Ltd.
• Reetz, Manfred T.; Drewes, Mark W.; Schmitz, Alfred, Angewandte Chemie, 1987, vol. 99, # 11, p. 1186 - 1188
  作者：Reetz, Manfred T.、Drewes, Mark W.、Schmitz, Alfred

  DOI：——

  日期：——