[1-(4-甲基苯磺酰基)-2-苯基乙基]氨基甲酸叔丁酯 | 914955-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [1-(4-甲基苯磺酰基)-2-苯基乙基]氨基甲酸叔丁酯
• 英文名称: [1-(4-methylbenzenesulfonyl)-2-phenylethyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[1-(4-methylphenyl)sulfonyl-2-phenylethyl]carbamate
• CAS: 914955-62-7
• 化学式: C₂₀H₂₅NO₄S
• 分子量: 375.489
• InChiKey: PAWXDRJWIZNLGN-UHFFFAOYSA-N

物化性质

• 沸点：
  565.0±50.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 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：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(4-甲基苯磺酰基)-2-苯基乙基]氨基甲酸叔丁酯 在 Schwartz's reagent 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 46.33h， 生成 (3S)-boc-3-氨基-4-苯基-2-丁酮
  参考文献：
  名称：

  Trisubstituted (E)-Alkene Dipeptide Isosteres as β-Turn Promoters in the Gramicidin S Cyclodecapeptide Scaffold

  摘要：

  A concise synthesis of a gramicidin S analogue with trisubstituted (E)-alkene dipeptide isostere (TEADI) replacements at both D-Phe-Pro positions was realized. Conformational analysis demonstrated that TEADIs can serve as type II beta-turn promoters in a cyclic scaffold and successfully mimic a proline residue.

  DOI：

  10.1021/ol0617704
• 作为产物：
  描述：

  p-toluenesulfonic acid 、 氨基甲酸叔丁酯 、 苯乙醛 以 乙醚 为溶剂， 以61%的产率得到[1-(4-甲基苯磺酰基)-2-苯基乙基]氨基甲酸叔丁酯
  参考文献：
  名称：

  Trisubstituted (E)-Alkene Dipeptide Isosteres as β-Turn Promoters in the Gramicidin S Cyclodecapeptide Scaffold

  摘要：

  A concise synthesis of a gramicidin S analogue with trisubstituted (E)-alkene dipeptide isostere (TEADI) replacements at both D-Phe-Pro positions was realized. Conformational analysis demonstrated that TEADIs can serve as type II beta-turn promoters in a cyclic scaffold and successfully mimic a proline residue.

  DOI：

  10.1021/ol0617704

文献信息

• Enantioselective Addition of Bromonitromethane to Aliphatic <i>N</i>-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst
  作者：Kenneth E. Schwieter、Jeffrey N. Johnston

  DOI：10.1021/acscatal.5b01901

  日期：2015.11.6

  This report details the enantioselective synthesis of β-amino-α-bromo nitroalkanes with β-alkyl substituents, using homogeneous catalysis to prepare either antipode. Use of a bifunctional Brønsted base/acid catalyst allows equal access to either enantiomer of the products, enabling the use of Umpolung Amide Synthesis (UmAS) to prepare the corresponding L- or D-α-amino amide bearing alkyl side chains—overall

  该报告详细介绍了使用均相催化制备对映体时，对具有β-烷基取代基的β-氨基-α-溴硝基硝基烷的对映选择性合成。使用双功能布朗斯台德碱/酸催化剂可以平等地获得产品的对映异构体，从而可以使用U酰胺合成（UmAS）制备相应的带有烷基侧链的L-或D-α-氨基酰胺。离醛仅四个步骤。该方法还解决了溴硝基甲烷和固体氢氧化物碱之间的潜在不相容性。
• Enantioselective synthesis of <scp>d</scp>-α-amino amides from aliphatic aldehydes
  作者：Kenneth E. Schwieter、Jeffrey N. Johnston

  DOI：10.1039/c5sc00064e

  日期：——

  Bromonitromethane is used in a phase transfer-catalysed enantioselective aza-Henry reaction, leading to D-amino amide bearing an alkyl chain.

  溴硝基甲烷用于相转移催化的对映选择性氮杂-亨利反应，生成带有烷基链的 D-氨基酰胺。
• Phase Transfer Catalyzed Enantioselective Strecker Reactions of α-Amido Sulfones with Cyanohydrins
  作者：Raquel P. Herrera、Valentina Sgarzani、Luca Bernardi、Francesco Fini、Daniel Pettersen、Alfredo Ricci

  DOI：10.1021/jo061566u

  日期：2006.12.1

  A study into the use of a chiral phase-transfer catalyst in conjunction with acetone cyanohydrin to effect the enantioselective formation of α-amino nitriles from α-amido sulfones is described. This novel catalytic asymmetric Strecker reaction is analyzed with regard to the possible mechanistic basis.

  描述了将手性相转移催化剂与丙酮氰醇结合使用以实现由α-酰胺基砜对映选择性形成α-氨基腈的研究。就可能的机理基础分析了这种新颖的催化不对称斯特雷克反应。
• An easy entry to optically active α-amino phosphonic acid derivatives using phase-transfer catalysis (PTC)
  作者：Francesco Fini、Gabriele Micheletti、Luca Bernardi、Daniel Pettersen、Mariafrancesca Fochi、Alfredo Ricci

  DOI：10.1039/b807027j

  日期：——

  The unprecedented use of phase-transfer catalysis (PTC) in an asymmetric hydrophosphonylation reaction allows the obtainment of a range of optically active α-amino phosphonic acid derivatives directly from α-amido sulfones.

  在不对称亲水磷腈反应中空前绝后地使用相转移催化（PTC），使得直接从α-酰胺砜获得一系列光学活性的α-氨基膦酸衍生物成为可能。
• Addition of Purines to N-Boc Imines Generated in Situ in Water: Efficient Synthesis of Novel Acyclic Purine Azanucleosides
  作者：Xiao-Mei Zhang、Hui Zhang、Chun-Xia Lian、Wei-Cheng Yuan

  DOI：10.1055/s-0031-1291043

  日期：2012.6

  A mild, efficient and highly regioselective addition of purine derivatives to N-Boc imines generated in situ in water was developed for the first time. A wide range of novel acyclic purine azanucleosides were synthesized in moderate to high yields through this transformation. This methodology was also appropriate for some other N-heterocycles.