benzyl N-[(2R)-3-methyl-1-oxobutan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate | 1064654-96-1

• 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: benzyl N-[(2R)-3-methyl-1-oxobutan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate
• CAS: 1064654-96-1
• 化学式: C₂₁H₂₄N₂O₅
• 分子量: 384.432
• InChiKey: OXKWEWXQKLGWBF-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2R)-3-methyl-1-oxobutan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate 在 锂硼氢 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 L-脯氨酸 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Proline-Catalyzed Asymmetric Synthesis of syn- and anti-1,3-Diamines

  摘要：

  A general organocatalytic strategy for asymmetric synthesis of both syn/anti-1,3-diamines has been developed. The strategy employs proline-catalyzed sequential alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step where syn-1,3-diamine was obtained as the most favorable product.

  DOI：

  10.1021/jo401722e
• 作为产物：
  描述：

  偶氮二甲酸二苄酯 、 异戊醛 在 L-脯氨酸 作用下， 以 碳酸丙烯酯 为溶剂， 反应 24.0h， 生成 benzyl N-[(2R)-3-methyl-1-oxobutan-2-yl]-N-(phenylmethoxycarbonylamino)carbamate
  参考文献：
  名称：

  Proline-Catalysed Amination Reactions in Cyclic Carbonate Solvents

  摘要：

  研究表明，在脯氨酸催化的醛和酮的 a-肼化反应中，碳酸丙烯酯是二氯甲烷和乙腈的环保型可持续替代品。即使使用较低的催化剂负载，也能获得与在传统溶剂或离子液体中获得的对映选择性相当的对映选择性。

  DOI：

  10.3390/molecules16043420

文献信息

• Heterogeneous Dipeptide-Catalyzed α-Amination of Aldehydes in a Continuous-Flow Reactor: Effect of Residence Time on Enantioselectivity
  作者：Sándor B. Ötvös、Aliz Szloszár、István M. Mándity、Ferenc Fülöp

  DOI：10.1002/adsc.201500375

  日期：2015.11.16

  A solid-supported dipeptide-catalyzed continuous-flow process was developed for the direct enantioselective α-amination of aldehydes with dibenzyl azodicarboxylate as the electrophilic nitrogen source. With residence time control as an efficient tool for the fine-tuning of the enantioselectivity, synthetically useful α-hydrazino alcohols were achieved with excellent ees. The packed-bed system proved

  开发了固相支持的二肽催化连续流工艺，用于以偶氮二羧酸二苄酯为亲电氮源直接对醛进行对映选择性α-胺化反应。利用停留时间控制作为微调对映选择性的有效工具，可以以优异的ee值获得合成有用的α-肼基醇。填充床系统被证明是高度耐用的：在整个连续流操作20小时内，未发现催化剂活性或选择性下降。
• Highly Efficient and Practical Pyrrolidine-Camphor-Derived Organocatalysts for the Direct α-Amination of Aldehydes
  作者：Pang-Min Liu、Dhananjay R. Magar、Kwunmin Chen

  DOI：10.1002/ejoc.201000695

  日期：2010.10

  for direct α-amination of aldehydes with dialkyl azodicarboxylates to give the desired α-aminated products in high chemical yields (up to 92 %) and with high to excellent levels of stereoselectivity (up to >99 % ee). The reactions proceeded rapidly (within 5 min) with low catalyst loading (5 mol-%) at ambient temperature. Enantioselective aminations of asymmetric α,α-disubstituted aldehydes in the catalytic

  设计并合成了一系列吡咯烷樟脑衍生的有机催化剂 (1-4)。这些有机催化剂用于醛与偶氮二羧酸二烷基酯的直接 α-胺化，以高化学产率（高达 92%）和高至极好的立体选择性（高达 >99% ee）得到所需的 α-胺化产物。反应在环境温度下以低催化剂负载量（5 mol%）快速进行（5 分钟内）。研究了催化体系中不对称 α,α-二取代醛的对映选择性胺化，获得了合理到高的立体选择性（高达 75% ee）。β-氨基-γ-丁内酯衍生物和具有高立体选择性的四取代环己烷衍生氨基醇的合成证明了该方法的实用性。为不对称α-胺化反应提出了过渡模型；它们涉及原位形成的亲核烯胺与氮源之间的氢键相互作用。
• Polymer-immobilized α,α-bis[bis-3,5-(trifluoromethyl)phenyl]prolinol silyl ether: synthesis and application in the asymmetric α-amination of aldehydes
  作者：Anton A. Guryev、Maksim V. Anokhin、Alexei D. Averin、Irina P. Beletskaya

  DOI：10.1016/j.mencom.2015.11.002

  日期：2015.11

  alpha,alpha-Bis[bis-3,5-(trifluoromethyl)phenyl]prolinol silyl ether anchored onto polystyrene was synthesized and tested in asymmetric alpha-amination of aldehydes. The catalytic activity and enantioselectivity of the immobilized catalyst persist for 3 cycles.
• Toward the optimization of continuous-flow aldol and α-amination reactions by means of proline-functionalized silicon packed-bed microreactors
  作者：Alessandro Massi、Alberto Cavazzini、Luisa Del Zoppo、Omar Pandoli、Valentina Costa、Luisa Pasti、Pier Paolo Giovannini

  DOI：10.1016/j.tetlet.2010.11.157

  日期：2011.2

  The activity and stability under flow conditions of covalently and non-covalently silica supported proline and proline-like organocatalysts is herein described. The slow aldol reaction of cyclohexanone with p-nitro benzaldehyde and the fast alpha-amination of isovaleraldehyde with dibenzyl azodicarboxylate have been selected as model reactions for this study. Prospects and limitations of the disclosed continuous-flow organocatalytic approach are widely discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Organocatalytic Sequential α-Amination−Horner−Wadsworth−Emmons Olefination of Aldehydes:  Enantioselective Synthesis of γ-Amino-α,β-Unsaturated Esters
  作者：Shriram P. Kotkar、Vilas B. Chavan、Arumugam Sudalai

  DOI：10.1021/ol063012j

  日期：2007.3.1

  A novel and highly enantioselective method for the synthesis of gamma-amino-alpha,beta-unsaturated esters via tandem alpha-amination-Horner-Wadsworth-Emmons (HWE) olefination of aldehydes is described. The one-pot assembly has been demonstrated for the construction of functionalized chiral 2-pyrrolidones, subunits present in several alkaloids.