(S)-N,N-dibenzyl-L-tert-leucinal | 155433-35-5

• 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: (S)-N,N-dibenzyl-L-tert-leucinal
• 英文别名: (2S)-2-(dibenzylamino)-3,3-dimethylbutanal
• CAS: 155433-35-5
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: SLHDZOBZGUQNKT-LJQANCHMSA-N

物化性质

• 沸点：
  381.7±30.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  7
• 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：

  (S)-N,N-dibenzyl-L-tert-leucinal 在 三丁基硼 、 三氟化硼乙醚 、 四氯化钛 、 三甲基乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.92h， 生成 methyl (4S,6R)-(-)-6-[(1S)-(dibenzylamino)-2,2-dimethylpropyl]-2,2-dimethyl-1,3-dioxane-4-acetate
  参考文献：
  名称：

  α-Heterosubstituted Aldehydes in Organic Synthesis. Enantioselective Approaches to New Analogues of Mevinic Acids

  摘要：

  本文描述了对HMG-CoA还原酶抑制剂的内酯部分进行不对称合成的多种醛缩反应方法。辅助控制和催化醛缩反应只能得到适度至低的选择性，而对易得到的高对映异构体α-杂基取代醛的1,2-加成则产生了具有高度对映异构体控制和良好化学收率的δ-羟基-β-酮酸酯。然后通过对加成产物的syn-还原获得了新型的梅维酸类似物。

  DOI：

  10.1135/cccc20030975
• 作为产物：
  描述：

  (S)-2-Dibenzylamino-3,3-dimethyl-butyric acid benzyl ester 生成 (S)-N,N-dibenzyl-L-tert-leucinal
  参考文献：
  名称：

  Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents

  摘要：

  The stereochemistry of the indium-promoted reaction of allyl bromide with alpha-thia (PhS and MeS), disubstituted alpha-amino (Bn2N, Me2N, isoindolyl), and protected alpha-amino aldehydes (Ac and Boc) in water has been evaluated. The reactions involving the sulfur derivatives are minimally diastereoselective, indicating that the allylindium reagent is not thiophilic. Chelation is not observed and pi-facial discrimination is achieved via Felkin-Ahn transition states under the steric control of the substituents. The Garner aldehyde is also anti-diastereoselective. Interestingly, N-acetylmannosamine is appreciably responsive to chelation control and is capable of generating 90% of the syn beta-amino alcohol when reacted in a 0.5 M NH4Cl solution. While the alpha-dibenzylamino substituent is too bulky to enter into complexation, the alpha-dimethylamino group is not and can lead to high levels (99%) of syn diastereomer. The size of other neighboring substituents does have an impact on pi-facial discrimination in these systems and can erode the stereoselectivity accordingly.

  DOI：

  10.1021/jo970274d

文献信息

• Synthesis and utilization of trifluoromethylated amino alcohol ligands for the enantioselective Reformatsky reaction and addition of diethylzinc to N-(diphenylphosphinoyl)imine
  作者：Xiu-Hua Xu、Xiao-Long Qiu、Feng-Ling Qing

  DOI：10.1016/j.tet.2008.05.043

  日期：2008.7

  successfully applied in the enantioselective Reformatsky reaction and addition of diethylzinc to N-(diphenylphosphinoyl)imine, respectively. The influence of the substituents on C-3 position and the amino moiety on the enantioselectivity has been carefully investigated. In the best cases, ligand 1b exhibited good selectivity for the enantioselective Reformatsky reaction in 86% ee and ligand 12d provided excellent

  设计并方便地制备了一系列三氟甲基化的氨基醇配体，分别成功地用于对映选择性的Reformatsky反应和将二乙基锌分别添加到N-（二苯基膦酰基）亚胺中。仔细研究了取代基对C-3位和氨基部分对映选择性的影响。在最佳情况下，配体1b对86％ee的对映选择性Reformatsky反应表现出良好的选择性，而配体12d通过向具有95％ee的N-（二苯基膦酰基）亚胺中添加二乙基锌，提供了出色的对映选择性。
• Synthesis of allylamines in enantiomerically pure form
  作者：José M Concellón、Beatriz Baragaña、Estela Riego

  DOI：10.1016/s0040-4039(00)00623-7

  日期：2000.6

  Enantiopure allylamines are obtained without racemization by reaction of α-amino aldehydes with chloromethyllithium followed by lithiation.

  通过α-氨基醛与氯甲基锂反应，然后锂化，得到不消旋的对映体烯丙基胺。
• Diastereo- and enantio-selective synthesis of 6-heterosubstituted-3,5-dihydroxyesters: novel precursors of mevinolin analogues
  作者：Dieter Enders、Frank Burkamp、Jan Runsink

  DOI：10.1039/cc9960000609

  日期：——

  The diastereoselective addition of 1,3-bis(trimethylsilyloxy)-1-methoxybutadiene 2 to readily available α-heterosubstituted aldehydes (S)-1 affords after syn-diastereoselective reduction HMG-CoA-reductase inhibitor-precursors (S,R,S)-4 and 5 with various substitution patterns and high enantiomeric and diastereoisomeric excesses (ee = 93–>96%; de = 95–>96%) in good yields.

  将 1,3-双（三甲基硅氧基）-1-甲氧基丁二烯 2 非对映选择性地加成到容易获得的α-异构醛（S）-1 中，经过同步-非对映选择性还原，可得到 HMG-CoA 还原酶抑制剂前体（S,R,S）-4 和 5，它们具有不同的取代模式和较高的对映异构体和非对映异构体过量率（ee = 93->96%；de = 95->96%），收率良好。
• Ipaktschi, Junes; Heydari, Akbar, Chemische Berichte, 1993, vol. 126, # 8, p. 1905 - 1912
  作者：Ipaktschi, Junes、Heydari, Akbar

  DOI：——

  日期：——
• Chiral ferrocenyl amino alcohols as catalysts for the enantioselective borane reduction of ketones
  作者：Thierry Brunin、Jérôme Cabou、Stéphanie Bastin、Jacques Brocard、Lydie Pélinski

  DOI：10.1016/s0957-4166(02)00338-5

  日期：2002.7

  The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalysts prepared in situ from chiral ferrocenyl amino alcohols. The corresponding chiral secondary amino alcohols were obtained with modest to high enantiomeric excesses (up to 90%) using (1S,2S)-2-amino-1-ferrocenyl-3,3-dimethyl-1-butanol 5c. (C) 2002 Published by Elsevier Science Ltd.