N-(tert-butoxycarbonyl)-N-(propyn-3-yl)glycine ethyl ester | 1349193-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-N-(propyn-3-yl)glycine ethyl ester
• 英文别名: n-Tert-butoxycarbonyl-propargylglycine ethyl ester；ethyl 2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-ynylamino]acetate
• CAS: 1349193-15-2
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: QZRPXQZPQGTPCA-UHFFFAOYSA-N

物化性质

• 沸点：
  305.1±35.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-N-(propyn-3-yl)glycine ethyl ester 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 N-[N4-(benzyloxycarbonyl)cytosin-1-ylacetyl]-N-(propyn-3-yl)glycine ethyl ester
  参考文献：
  名称：

  Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs

  摘要：

  Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.124
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydride 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 20.0h， 生成 N-(tert-butoxycarbonyl)-N-(propyn-3-yl)glycine ethyl ester
  参考文献：
  名称：

  Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs

  摘要：

  Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.124

文献信息

• Tuning the Regioselectivity of Gold-Catalyzed Internal Nitroalkyne Redox: A Cycloisomerization and [3 + 2]-Cycloaddition Cascade for the Construction of <i>spiro</i>-Pseudoindoxyl Skeleton
  作者：Chepuri V. Suneel Kumar、Chepuri V. Ramana

  DOI：10.1021/ol502213w

  日期：2014.9.19

  tricyclic core present in the spiro-pseudoindoxyl natural products has been developed. This involves two intramolecular events: the Au-catalyzed nitroalkyne redox leading to isatogen and its subsequent [3 + 2]-cycloaddition with a suitably positioned olefin. The option to modulate the size of the spiro-annulated ring, which is an important variable in this class of natural products, has been explored. Overall

  已经开发出一种简单的用于在螺-伪吲哚酚天然产物中存在的三环核的构建的多米诺方法。这涉及两个分子内事件：Au催化的硝基炔氧化还原反应会生成致突变物，以及随后发生的[3 + 2]-环加成反应，并带有适当定位的烯烃。来调节大小的选项螺稠环，这是在这个类天然产物的一个重要变量，已探索。总体而言，此过程将线性前体成型为具有完整步骤，原子和氧化还原经济性的三环系统。
• Method for producing optically active N-protected-propargylglycine
  申请人：Takekawa Yuki

  公开号：US20060216806A1

  公开（公告）日：2006-09-28

  A method for producing (S)-N-protected-propargylglycine of the following formula (2), wherein the method comprises asymmetrically hydrolyzing an N-protected-propargylglycine ester of the following formula (1) by using the following asymmetric hydrolysis enzyme or a cultured substance of a microorganism having an ability of producing this enzyme or a treated substance thereof. [Asymmetric Hydrolysis Enzyme] Hydrolysis enzymes derived from a microorganism selected from the group consisting of Thermomyces genus, Aspergillus genus, Rhizopus genus, Penicillium genus, Pseudomonas genus, Humicola genus, Burkholderia genus, Candida genus and Streptomyces genus.

  一种制备(S)-N-保护-丙炔基甘氨酸的方法，其中该方法包括使用以下不对称水解酶或具有产生该酶或其处理物能力的微生物培养物或其处理物，通过不对称水解以下式子（1）中的N-保护-丙炔基甘氨酸酯，来制备以下式子（2）中的目标产物。 【不对称水解酶】来自以下微生物中的水解酶：Thermomyces属，Aspergillus属，Rhizopus属，Penicillium属，Pseudomonas属，Humicola属，Burkholderia属，Candida属和Streptomyces属。
• US7645607B2
  申请人：——

  公开号：US7645607B2

  公开（公告）日：2010-01-12
• Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs
  作者：Nicola M. Howarth、Jennyfer Ricci (née Goujon)

  DOI：10.1016/j.tet.2011.09.124

  日期：2011.12

  Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment. (C) 2011 Elsevier Ltd. All rights reserved.