2-Dibenzylamino-4-methyl-pentanal

• 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: 2-Dibenzylamino-4-methyl-pentanal
• 英文别名: Pentanal, 2-[bis(phenylmethyl)amino]-4-methyl-；2-(dibenzylamino)-4-methylpentanal
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: MTCXPHZCBACKKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Dibenzylamino-4-methyl-pentanal 在 吡啶 、 盐酸 、 正丁基锂 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， -78.0~90.0 ℃ 、506.66 kPa 条件下， 反应 104.5h， 生成 (S,S)-4-(N-acetylamino)-5-isobutylpyrrolidin-2-one
  参考文献：
  名称：

  Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

  摘要：

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

  DOI：

  10.1021/ol203011u
• 作为产物：
  描述：

  DL-亮氨酸 在 lithium aluminium tetrahydride 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2-Dibenzylamino-4-methyl-pentanal
  参考文献：
  名称：

  Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

  摘要：

  Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N(alpha-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide to a range of racemic acyclic gamma-amino-alpha,beta-unsaturated esters (derived from the corresponding a-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure beta,gamma-diamino esters. The beta,gamma-dlamlno ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

  DOI：

  10.1021/ol203011u

文献信息

• Synthesis of Enantiomerically and Diastereomerically Pure 4-Hydroxy-1,2-alkadienyl Carbamates and Their Application in a Modified Nazarov Cyclization Towards Chiral Cyclopentenones
  作者：Dieter Hoppe、Maik Zimmermann、Birgit Wibbeling

  DOI：10.1055/s-2004-816002

  日期：——

  The addition of racemic titanated alkynyl N,N-diisopropylcarbamates onto enantiopure α-dibenzylamino- or a-silyloxyalkanals affords two (out of four possible) diastereomeric, enantiopure 5-hetero-substituted 4-hydroxy-1,2-alkadienyl carbamates. As demonstrated for hydroxyallenes 23 and 24, the reaction sequence for modified Nazarov cyclization according to Tius, yields stereohomogeneous, highly substituted

  将外消旋的钛化炔基 N,N-二异丙基氨基甲酸酯添加到对映纯的 α-二苄基氨基-或α-甲硅烷氧基链烷醛上，得到两种（四种可能的）非对映体、对映纯 5-杂取代的 4-羟基-1,2-链二烯基氨基甲酸酯。正如羟基丙二烯 23 和 24 所证明的，根据 Tius 进行改性 Nazarov 环化的反应序列产生立体均相、高度取代的 5-亚烷基-2,3-二烷基-4-苯基-2-环戊烯-1-酮 (Z,R) -25 和 (E, R)-26。
• Stereoselective synthesis of 3(2H)-dihydrofuranones by addition of lithiated methoxyallene to chiral aldehydes
  作者：Stephan Hormuth、Hans Ulrich Reissig

  DOI：10.1021/jo00080a013

  日期：1994.1

  Lithiated methoxyallene 2 adds to chiral aldehydes such as 5-phenylpropanal and N,N-dibenzylated alpha-amino aldehydes 4-8 to give products 9-14 in good yields and with excellent anti-selectivity. The stereochemical outcome of these reactions can be explained by the Felkin-Anh model in a straightforward manner. The crude reaction products can either be transformed to enones by hydrolysis with acid or be converted into 2,5-dihydro-3-methoxyfuran derivatives 19-24 by treatment with potassium tert-butoxide in DMSO. The latter can be hydrolyzed to give 3(2H)-dihydrofuranones 25-29. The diastereoselectivity of the initial addition step is transferred to the dihydrofuran derivative without a major change in the isomer ratio. Compounds derived from alpha-amino aldehydes 5, 6, and 8 are assumed to be enantiomerically pure. Sodium borohydride reductions of and Grignard additions to 3(2H)-dihydrofuranones 27a and 28a demonstrate that these chiral ketones react in a highly diastereoselective manner. In summary, this paper shows that lithiated methoxyallene 2 can serve as a very useful equivalent for alpha,beta-unsaturated acyl anions and 1,3-dipolar synthons in asymmetric synthesis.
• PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY PURE (S,S) AMINOEPOXIDES, KEY INTERMEDIATES FOR HIV PROTEASE INHIBITORS, VIA THEIR CHLOROHYDRINES
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP0796239B1

  公开（公告）日：1999-03-31
• US4990669A
  申请人：——

  公开号：US4990669A

  公开（公告）日：1991-02-05
• US5550291A
  申请人：——

  公开号：US5550291A

  公开（公告）日：1996-08-27