(S)-benzyl (1-bromo-3-phenylpropan-2-yl)carbamate | 676457-76-4

• 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)-benzyl (1-bromo-3-phenylpropan-2-yl)carbamate
• 英文别名: benzyl N-[(2S)-1-bromo-3-phenylpropan-2-yl]carbamate
• CAS: 676457-76-4
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: FQEVFEWFMUCQAQ-INIZCTEOSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  464.9±45.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-benzyl (1-bromo-3-phenylpropan-2-yl)carbamate 在 Hoveyda-Grubbs catalyst second generation 、 三氟甲磺酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (3S,5R)-benzyl 3-benzyl-5-(2-oxopropyl)thiomorpholine-4-carboxylate
  参考文献：
  名称：

  Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts

  摘要：

  An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd (II) complex or strong Bronsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.

  DOI：

  10.1021/ol202276h
• 作为产物：
  描述：

  Z-L-苯丙氨醇 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以94%的产率得到(S)-benzyl (1-bromo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  N-溴代琥珀酰亚胺在Appel反应条件下促进β-氨基溴化物的合成

  摘要：

  摘要 已经开发了一种有效且简便的方法，用于在 Appel 反应条件下从相应的醇合成手性β-氨基溴化物。这种方法允许在温和条件下以优异的产率对各种β-氨基醇进行脱氧溴化，而没有任何可检测的外消旋化。

  DOI：

  10.1080/00397911.2021.1955270

文献信息

• Optically Active N- and C-Terminal Building Blocks for the Synthesis of Peptidyl Olefin Peptidomimetics
  作者：Sima Mirilashvili、Naama Chasid-Rubinstein、Amnon Albeck

  DOI：10.1002/ejoc.201000539

  日期：2010.8

  peptidomimetics serve as biologically active compounds or as intermediates for other peptidyl isosteres. The N-terminal side of the C=C bond could be easily prepared in an optically pure form from α-amino acids. Synthesis of C-terminal building blocks in an optically pure form is more challenging. We developed a chemoenzymatic stereoselective approach to such optically active C-terminal building blocks to

  肽基烯烃肽模拟物用作生物活性化合物或用作其他肽基等排体的中间体。C=C 键的 N 端侧可以很容易地从 α-氨基酸以光学纯的形式制备。以光学纯形式合成 C 端结构单元更具挑战性。我们开发了一种化学酶立体选择性方法，用于通过各种反应组装成肽基烯烃的光学活性 C 端结构单元。它们包括亲电子醛和亲核砜、鏻盐、膦酸盐和二硒化物。前手性二酯到相应羟基酯的关键酶水解引入了光学活性。随后化学反应的顺序，无论是保护-水解-功能化还是功能化-水解-保护，
• Highly Enantioselective Reactions of Cyclohexanone and<i>β</i>,<i>γ</i>-Unsaturated<i>α</i>-Keto Ester: The Tuning of Chemo-selectivities by Secondary and Primary Amine Catalysts
  作者：Jianwei Wei、Wengang Guo、Xin Zhou、Xin Du、Yan Liu、Can Li

  DOI：10.1002/cjoc.201400431

  日期：2014.10

  amphiphilic imidazole based secondary and primary amine catalysts were synthesized and shown to be very effective with an acid cocatalyst for the asymmetric reaction of cyclohexanone to β,γ‐unsaturated α‐keto ester. Interestingly, primary and secondary amine catalysts show different regio‐selectivities in this reaction. Under the catalysis of secondary amine 1, excellent enantioselectivities were observed for

  合成了一系列基于两亲咪唑的仲胺和伯胺催化剂，它们显示出与酸助催化剂非常有效地使环己酮不对称反应成β，γ-不饱和α-酮酯。有趣的是，伯胺和仲胺催化剂在该反应中显示出不同的区域选择性。在仲胺1的催化下，以水为溶剂，环己酮与β，γ-不饱和α-酮酯直接3 + 3反应生成的产物具有极好的对映选择性。而且，相同的反应物被伯胺2催化导致醛醇缩合反应，从而提供具有高非对映选择性和高达97％ee的相应产物。使用气相模型对过渡态进行的理论研究表明，空间效应对仲胺1和伯胺2的不同化学选择性诱导起着重要作用。
• Inhibition of α-chymotrypsin with thiol-bearing substrate analogues in the presence of zinc ion
  作者：Min Su Han、Dong Ju Oh、Dong H. Kim

  DOI：10.1016/j.bmcl.2003.11.058

  日期：2004.2

  We have demonstrated that thiol-bearing analogues of alpha-chymotrysin (alpha-CT) substrates such as (S)-(1-benzyl-2-thiolethyl)-carbamic acid, benzyl ester (3) inhibits (alpha-CT, a prototypical serine protease, in the presence of Zn(II) ion. They constitute a novel class of small molecule inhibitors for alpha-CT believed to inhibit the enzyme by forming a ternary complex consisting of alpha-CT, Zn(II) ion, and the inhibitor. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction
  作者：Brian M. Cochran、Forrest E. Michael

  DOI：10.1021/ol702891p

  日期：2008.1.1

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.
• Stereoselective synthesis of 1,3-substituted tetrahydroisoquinolines through palladium-catalyzed three-component reaction
  作者：Raffaella Ferraccioli、Clelia Giannini、Giorgio Molteni

  DOI：10.1016/j.tetasy.2007.05.031

  日期：2007.7

  Chiral 1,3-substituted 1,2,3,4-tetrahydroisoquinolines have been synthesized in acceptable yield and diastereoselectivity through a three component reaction, starting from aromatic halides, enantiopure bromoalkyl derivatives and methyl acrylate, under palladium catalysis. (c) 2007 Elsevier Ltd. All rights reserved.