2-<<(propyn-2-yl)oxycarbonyl>methoxy>acetic acid propargyl ester | 135609-62-0

• 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: 2-<<(propyn-2-yl)oxycarbonyl>methoxy>acetic acid propargyl ester
• 英文别名: di(prop-2-yn-1-yl) 2,2'-oxydiacetate；Prop-2-ynyl 2-(2-oxo-2-prop-2-ynoxyethoxy)acetate
• CAS: 135609-62-0
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: QTAHFGLGDQGBIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-叠氮基-2-(2-叠氮基乙氧基)乙烷 、 2-<<(propyn-2-yl)oxycarbonyl>methoxy>acetic acid propargyl ester 在 copper(I) trifluoromethanesulfonate benzene 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 以5%的产率得到
  参考文献：
  名称：

  铜催化的[1,3]-偶极环加成反应合成含无环，芳香和甾族部分的大环

  摘要：

  铜催化的1，3-偶极环加成反应用于合成一系列具有无环，芳族和甾族片段的含双（1,2,3-三唑）的大环。研究了取代基的性质对叠氮化物的影响以及底物中二烯键连接链的长度对产物收率的影响。通过双（胆烷）-24,24'-二叠氮化物与脂族二炔丙基酯的反应或双（胆烷）-24,24'-二炔丙基酯与芳族二叠氮化物的反应或胆汁酸的环化-二聚反应来制备含有甾体片段的大环化合物在同一分子中同时具有叠氮基和乙炔基的衍生物。 1,3-偶极环加成-叠氮化物-胆烷-铜-大环化合物

  DOI：

  10.1055/s-0029-1217400
• 作为产物：
  描述：

  在 rhodium(II) acetate dimer 、 盐酸 、 acetate buffer 、 水 、 sodium nitrite 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-<<(propyn-2-yl)oxycarbonyl>methoxy>acetic acid propargyl ester
  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

• TMSCl Promoted Direct Conversion of Cyclic Anhydrides to (Un)Symmetric‐Diesters/Amide Esters
  作者：Meera Johny、Amuda Manikandan、Goreti Rajendar

  DOI：10.1002/asia.202301017

  日期：2024.2

  A mild, novel, and efficient silyl-promoted conversion of cyclic anhydride to diesters and amide esters. The reaction follows a two-step process, ring opening of anhydride by amine or alcohol following esterification. The reaction was carried out in the presence and absence of base. The method has broad substrate scope and is applicable for the synthesis of commercial plasticizers.

  一种温和、新颖且高效的甲硅烷基促进环酸酐向二酯和酰胺酯的转化。该反应分两步进行，酯化后通过胺或醇使酸酐开环。反应在碱存在和不存在下进行。该方法底物范围广泛，适用于商业增塑剂的合成。
• 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：——
• Copper-Catalyzed [1,3]-Dipolar Cycloaddition for the Synthesis of Macrocycles Containing Acyclic, Aromatic and Steroidal Moieties
  作者：Nikolay Lukashev、Gennadij Latyshev、Mikhail Baranov、Alexei Kazantsev、Alexei Averin、Irina Beletskaya

  DOI：10.1055/s-0029-1217400

  日期：2009.8

  bis(cholane)-24,24′-diazides with aliphatic dipropargyl esters, or bis(cholane)-24,24′-dipropargyl esters with aromatic diazides, or by cyclization-dimerization of bile acid derivatives possessing both azide and acetylene groups in the same molecule. 1,3-dipolar cycloaddition - azides - cholaphanes - copper - macrocycles

  铜催化的1，3-偶极环加成反应用于合成一系列具有无环，芳族和甾族片段的含双（1,2,3-三唑）的大环。研究了取代基的性质对叠氮化物的影响以及底物中二烯键连接链的长度对产物收率的影响。通过双（胆烷）-24,24'-二叠氮化物与脂族二炔丙基酯的反应或双（胆烷）-24,24'-二炔丙基酯与芳族二叠氮化物的反应或胆汁酸的环化-二聚反应来制备含有甾体片段的大环化合物在同一分子中同时具有叠氮基和乙炔基的衍生物。 1,3-偶极环加成-叠氮化物-胆烷-铜-大环化合物
• Synthesis and carbene decomposition of functionally substituted diazoacetate esters. 6. Propargyl diazoacetate
  作者：E. A. Shapiro、A. B. Dyatkin、O. M. Nefedov

  DOI：10.1007/bf00961353

  日期：1991.5

  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.