(氰基-苯基-甲基)-氨基甲酸叔丁酯 | 78558-73-3

• 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: (氰基-苯基-甲基)-氨基甲酸叔丁酯
• 英文名称: 2-(tert-butoxycarbonylamino)-2-phenylacetonitrile
• 英文别名: (cyano-phenyl-methyl)-carbamic acid tert-butyl ester；2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile；(cyanophenylmethyl)carbamic acid tert-butyl ester；tert-butyl [cyano(phenyl)methyl]carbamate；N-Boc-amino-phenylacetonitrile；BOC-ON；tert-butyl N-[cyano(phenyl)methyl]carbamate
• CAS: 78558-73-3
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: UWMFDFGRVUUNOU-UHFFFAOYSA-N

物化性质

• 熔点：
  110.9-112.8 °C
• 沸点：
  367.8±35.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.12
• 氢给体数：
  1.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  (氰基-苯基-甲基)-氨基甲酸叔丁酯 在 sodium azide 、 zinc dibromide 作用下， 以 水 、 异丙醇 为溶剂， 反应 16.0h， 以88%的产率得到(+/-)-N-tert-butoxycarbonyl phenylglycine tetrazole
  参考文献：
  名称：

  An Expedient Route to the Tetrazole Analogues of α-Amino Acids

  摘要：

  [GRAPHIC]Convenient conditions are described for the transformation of alpha-aminonitriles to the tetrazole analogues of alpha-amino acids. Refluxing the starting material in water/2-propanol at 80 degreesC with sodium azide and catalytic zinc bromide affords the tetrazole product in yields generally exceeding 90%.

  DOI：

  10.1021/ol020096x
• 作为产物：
  描述：

  (S)-tert-butyl 2-amino-2-oxo-1-phenylethylcarbamate 在 TEA 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以100%的产率得到(氰基-苯基-甲基)-氨基甲酸叔丁酯
  参考文献：
  名称：

  Novel thiazolones as HCV NS5B polymerase allosteric inhibitors: Further designs, SAR, and X-ray complex structure

  摘要：

  Structure-activity relationships (SAR) of 1 against HCV NS5B polymerase were described. SAR explorations and further structure-based design led to the identifications of 2 and 3 as novel HCV NS5B inhibitors. X-ray structure of 3 in complex with NS5B polymerase was obtained at a resolution of 2.2A, and confirmed the design.

  DOI：

  10.1016/j.bmcl.2006.09.095

文献信息

• Gamma-hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamides and uses thereof
  申请人：Merck & Co., Inc.

  公开号：US06642237B1

  公开（公告）日：2003-11-04

  &ggr;-Hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamide compounds are inhibitors of HIV protease and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. These compounds are effective against HIV viral mutants which are resistant to HIV protease inhibitors currently used for treating AIDS and HIV infection.

  -Hydroxy-2-(氟烷基氨基甲酰)-1-哌嗪戊二酰胺化合物是HIV蛋白酶的抑制剂，也是HIV复制的抑制剂。这些化合物在预防或治疗HV感染以及治疗艾滋病方面非常有用，无论是作为化合物、药学上可接受的盐、药物组成成分，还是与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。还描述了治疗艾滋病的方法以及预防或治疗HIV感染的方法。这些化合物对目前用于治疗艾滋病和HIV感染的HIV蛋白酶抑制剂产生耐药性的HIV病毒突变体具有有效作用。
• Electrophilic amination of enolates with oxaziridines: effects of oxaziridine structure and reaction conditions
  作者：Alan Armstrong、Ian D. Edmonds、Martin E. Swarbrick、Nigel R. Treweeke

  DOI：10.1016/j.tet.2005.06.085

  日期：2005.8

  A range of N-alkoxycarbonyl- and N-carboxamido-oxaziridines has been prepared to test the effects of oxaziridine structure on yields of enolate amination product. Side-products arising from reaction of aldehyde-derived oxaziridines with base were identified, while a ketone-derived oxaziridine afforded moderate yields of amination product with stabilised carbanions.

  已经制备了一系列的N-烷氧基羰基-和N-羧酰胺基-恶唑烷，以测试恶唑烷结构对烯醇化胺产物的产率的影响。鉴定了醛衍生的恶唑烷与碱反应产生的副产物，而酮衍生的恶唑烷提供了中等产率的胺化产物和稳定的碳负离子。
• Dual-Activation Asymmetric Strecker Reaction of Aldimines and Ketimines Catalyzed by a Tethered Bis(8-quinolinolato) Aluminum Complex
  作者：Joshua P. Abell、Hisashi Yamamoto

  DOI：10.1021/ja907268g

  日期：2009.10.28

  aldimines and ketimines. Although catalytic asymmetric addition of cyanide to imines to generate alpha-amino-protected nitriles (the Strecker reaction) has been extensively studied in the past, alternative, easier-to-handle reagents for this process are required for modern organic synthesis. To date, there are a limited number of reports utilizing alternative sources of cyanide other than KCN/HCN or TMSCN

  发现铝配合物对于将氰化物添加到醛亚胺和酮亚胺中具有高产率和对映选择性。尽管过去已经广泛研究了将氰化物催化不对称加成到亚胺以生成 α-氨基保护的腈（Strecker 反应），但现代有机合成需要用于该过程的替代性、更易于处理的试剂。迄今为止，在这一重要反应中使用除 KCN/HCN 或 TMSCN 之外的其他氰化物来源的报告数量有限。本催化剂使用氰基甲酸乙酯作为氰化物源为芳族、杂芳族和脂族醛亚胺和酮亚胺提供均匀的高对映选择性。
• Photoreactive fused aziridinylpiperazines on the background of 4-substituted chalcones and their benzimidazolic analogs
  作者：Volodymyr M. Kotlyar、Oleksii O. Kolomoitsev、Dmytro V. Nikolaievskyi、Polina I. Pedan、Andrii Yu Chumak、Valery D. Orlov、Svitlana V. Shishkina、Andrey O. Doroshenko

  DOI：10.1016/j.molstruc.2018.12.015

  日期：2019.3

  Abstract The reaction of bromo-substituted chalcones with various diamino-compounds leads to the fused heterocyclic products, aziridinylpiperazines, exhibiting photoreactivity in the crystalline state. Crystals of 4-nitrosubstituted compounds of this family change their color from yellowish to deep violet-blue, 4-cyanosubstituted ones – from yellowish to pink at UV irradiation. Discussion on the mechanism

  摘要 溴代查耳酮与各种二氨基化合物反应生成稠合杂环产物氮丙啶基哌嗪，在结晶状态下表现出光反应性。该家族的 4-硝基取代化合物晶体的颜色从淡黄色变为深紫蓝色，4-氰基取代化合物的颜色在紫外线照射下从淡黄色变为粉红色。关于这种光转化机制的讨论仍在进行中，然而，有几个事实表明光生有色半成品的自由辐射性质仅通过照射样品的结晶状态稳定。在合成标题化合物时，在溴查耳酮与脂肪族/脂环族或芳香族系列的不对称二胺相互作用时形成位置异构体的混合物也具有重要意义。
• Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions
  作者：Ki-Tae Kang、Sang Hyun Park、Do Hyun Ryu

  DOI：10.1021/acs.orglett.9b02280

  日期：2019.9.6

  Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yield (up to 98%) with high to excellent enantioselectivity (up to 99% ee). A rational mechanistic model for the complex of COBI and aldimine is provided

  已经开发了使用氰化三丁基锡和烯丙基三丁基锡烷的手性恶唑硼烷鎓离子（COBI）催化的醛亚胺的对映选择性亲核加成反应。以高产率（高达98％）和高至极好的对映选择性（高达99％ee）合成了各种α-氨基腈和均烯丙基胺。提供了用于COBI和醛亚胺复合物的合理机理模型来解释这些对映选择性反应。