propargyl aminoacetate hydrochloride | 135609-54-0

• 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: propargyl aminoacetate hydrochloride
• 英文别名: 2-propynyl glycinate hydrochloride；prop-2-ynyl 2-aminoacetate;hydrochloride
• CAS: 135609-54-0
• 化学式: C₅H₇NO₂*ClH
• 分子量: 149.577
• InChiKey: GJWQKEKFHALIGC-UHFFFAOYSA-N

物化性质

• 熔点：
  158 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.46
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  propargyl aminoacetate hydrochloride 在 acetate buffer 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到propargyl diazoacetate
  参考文献：
  名称：

  Synthesis and carbene decomposition of functionally substituted diazoacetate esters. 6. Propargyl diazoacetate

  摘要：

  A synthesis of propargyl diazoacetate (I) was carried out and its chemical transformations were studied. The reaction of (I) in the presence of Rh(OAc)2 at 25-degrees-C with 1-pentyne gives the propargyl ester of 1-propylcyclopropene-3-carboxylic acid in 80% yield, while reaction with 2,3-dimethyl-2-butene at 60-degrees-C results in the propargyl ester of tetramethylcyclopropanecarboxylic acid in 10% yield. Compound (I) reacts under the same conditions (35-60-degrees-C) with ether, CH2Cl2 and water, with the formation of propargyl esters of ethoxy-acetic, 2,3-dichloropropionic, and a mixture of glycols and 2-{[(propyn-2-yl)oxycarbonyl]methoxy} acetic acids in yields of up to 35%. A spontaneous oligomerization of (I) was observed as a result of a dipolar [1, 3]-cycloaddition of the CH = N2 fragment of one molecule of (I) to the terminal-triple bond of the second molecule with the formation of oligomers of 3-hydroxymethylpyrazole-5-carboxylic acid.

  DOI：

  10.1007/bf00961353
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醚 为溶剂， 生成 propargyl aminoacetate hydrochloride
  参考文献：
  名称：

  Synthesis and carbene decomposition of functionally substituted diazoacetate esters. 6. Propargyl diazoacetate

  摘要：

  A synthesis of propargyl diazoacetate (I) was carried out and its chemical transformations were studied. The reaction of (I) in the presence of Rh(OAc)2 at 25-degrees-C with 1-pentyne gives the propargyl ester of 1-propylcyclopropene-3-carboxylic acid in 80% yield, while reaction with 2,3-dimethyl-2-butene at 60-degrees-C results in the propargyl ester of tetramethylcyclopropanecarboxylic acid in 10% yield. Compound (I) reacts under the same conditions (35-60-degrees-C) with ether, CH2Cl2 and water, with the formation of propargyl esters of ethoxy-acetic, 2,3-dichloropropionic, and a mixture of glycols and 2-{[(propyn-2-yl)oxycarbonyl]methoxy} acetic acids in yields of up to 35%. A spontaneous oligomerization of (I) was observed as a result of a dipolar [1, 3]-cycloaddition of the CH = N2 fragment of one molecule of (I) to the terminal-triple bond of the second molecule with the formation of oligomers of 3-hydroxymethylpyrazole-5-carboxylic acid.

  DOI：

  10.1007/bf00961353

文献信息

• 2-Benzoylpyridine Ligand Complexation with Gold Critical for Propargyl Ester-Based Protein Labeling
  作者：Yixuan Lin、Kenward Vong、Koji Matsuoka、Katsunori Tanaka

  DOI：10.1002/chem.201802058

  日期：2018.7.25

  reported work, AuIII complexes coordinated with 2‐benzoylpyridine ligand, BPy‐Au, were prebound to a protein and used to discover a novel protein‐directed labeling approach with propargyl ester functional groups. In this work, further examination discovered that gold catalysts devoid of the 2‐benzoylpyridine ligand (e.g., NaAuCl4) had significantly reduced levels of protein labeling. Mechanistic investigations

  在先前报道的工作中，与2-苯甲酰基吡啶配体BPy-Au配位的Au III复合物预先结合到蛋白质上，并用于发现具有炔丙基酯官能团的新型蛋白质定向标记方法。在这项工作中，进一步的检查发现，不含2-苯甲酰基吡啶配体（例如NaAuCl4）的金催化剂的蛋白质标记水平显着降低。然后，机理研究表明，BPy-Au和炔丙基酯会经历C（sp 2）-C（sp）芳基-炔基交叉偶联，可能是通过自发的还原消除。总体而言，这些观察结果似乎表明，BPy-Au介导的基于炔丙基酯的蛋白质标记是通过活化的酯中间体起作用的，这有助于我们了解这一过程，并将有助于在未来的生物缀合中扩展/优化金催化剂的使用。应用，尤其是体内。
• In Vivo Gold Complex Catalysis within Live Mice
  作者：Kazuki Tsubokura、Kenward K. H. Vong、Ambara R. Pradipta、Akihiro Ogura、Sayaka Urano、Tsuyoshi Tahara、Satoshi Nozaki、Hirotaka Onoe、Yoichi Nakao、Regina Sibgatullina、Almira Kurbangalieva、Yasuyoshi Watanabe、Katsunori Tanaka

  DOI：10.1002/anie.201610273

  日期：2017.3.20

  Metal complex catalysis within biological systems is largely limited to cell and bacterial systems. In this work, a glycoalbumin–AuIII complex was designed and developed that enables organ‐specific, localized propargyl ester amidation with nearby proteins within live mice. The targeted reactivity can be imaged through the use of Cy7.5‐ and TAMRA‐linked propargyl ester based fluorescent probes. This

  生物系统内的金属络合物催化主要限于细胞和细菌系统。在这项工作中，设计和开发了一种糖清蛋白-Au III复合物，它能够在活小鼠体内与附近的蛋白质进行器官特异性的、局部的炔丙酯酰胺化。可以通过使用 Cy7.5 和 TAMRA 连接的炔丙酯基荧光探针对靶向反应性进行成像。该靶向系统可以为生物医学和临床应用开发其他金属催化策略。
• The Synthesis and Selective Cytotoxicity of New Mannich Bases, Derivatives of 19- and 28-Alkynyltriterpenoids
  作者：E. F. Khusnutdinova、G. N. Apryshko、A. V. Petrova、O. S. Kukovinets、O. B. Kazakova

  DOI：10.1134/s1068162018010090

  日期：2018.1

  New propargylamines were synthesized in 72–75% yields by the interaction of 19-alkynylbetulin and 28-O-propargyl glycinamide of oleanolic acid with N-methylpiperazine under the Mannich reaction conditions. 19-[1-Methyl-4-prop-2-yn-1-yl-piperazine]-20,29,30-trinorbetulin was shown to manifest anticancer activity against one line of leukemia cells and two lines of colon cancer cells, whereas the growth

  在曼尼希反应条件下，通过齐墩果酸的 19-炔基白桦醇和 28-O-炔丙基甘氨酰胺与 N-甲基哌嗪的相互作用，以 72-75% 的产率合成了新的炔丙基胺。19-[1-Methyl-4-prop-2-yn-1-yl-piperazine]-20,29,30-trinorbetulin 显示出对一种白血病细胞系和两种结肠癌细胞系的抗癌活性，而白血病细胞 SR 在 4-(4-methylpiperazin-1-yl)but-2-yn-1-yl-N-(3-hydroxy-28-oxoolean-12-en-28-yl) 存在下的生长甘氨酸为 8%。
• NOVEL ARTIFICIAL PROTEIN CATALYST
  申请人：Glytech, Inc.

  公开号：EP3978023A1

  公开（公告）日：2022-04-06

  [Problem] To provide a novel artificial protein catalyst that enables the protection of a catalyst from substances in vivo and has potential usefulness in therapeutic in vivo synthetic chemistry. [Solution] Provided is a complex of a protein and a catalyst selected from a metal catalyst or organic catalyst. In the complex according to the present invention, the protein is a protein having a hydrophobic pocket in the three-dimensional structure thereof, and the catalyst is housed in the hydrophobic pocket so that the catalyst is not or substantially not exposed to a hydrophilic environment.

  [问题] 提供一种新型的人工蛋白质催化剂，使其能够保护催化剂免受体内物质的损害，并在体内治疗性合成化学中具有潜在用途。 [解决方案] 提供一种由蛋白质和催化剂（选自金属催化剂或有机催化剂）组成的复合物。在本发明的复合物中，蛋白质是一种具有三维结构中疏水口袋的蛋白质，而催化剂被容纳在疏水口袋中，从而使得催化剂不或几乎不暴露于亲水环境。
• SHAPIRO, E. A.;DYATKIN, A. B.;NEFEDOV, O. M., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1051-1056
  作者：SHAPIRO, E. A.、DYATKIN, A. B.、NEFEDOV, O. M.

  DOI：——

  日期：——