dimethyl 1,3,4-oxadiazole-2,5-dicarboxylate | 117601-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 1,3,4-oxadiazole-2,5-dicarboxylate
• 英文别名: 2,5-di(metoxycarbonyl)-1,3,4-oxadiazole；2,5-Bis(methoxycarbonyl)-1,3,4-oxadiazole
• CAS: 117601-09-9
• 化学式: C₆H₆N₂O₅
• 分子量: 186.124
• InChiKey: KJLNYDJOUIQDNX-UHFFFAOYSA-N

物化性质

• 沸点：
  277.7±23.0 °C(Predicted)
• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 1,3,4-oxadiazole-2,5-dicarboxylate 生成 2,6-Dimethoxycarbonyl-4H-pyran
  参考文献：
  名称：

  diels-alder-reaktionen中的1,3,4-恶二唑als异氰酸酯4π-komponenten

  摘要：

  恶二唑与角应变，烯烃和炔反应生成单-和bisadducts ，，与分子氮的损失。环丙烯的使用为γ-吡喃开辟了一条新途径。乙胺也可以作为炔烃反应生成呋喃衍生物。

  DOI：

  10.1016/0040-4039(88)85129-3

文献信息

• syn-Facial hetero-bridged [n]polynorbornanes: a new class of polarofacial framework molecules composed of fused 7-oxa- and 7-azanorbornanes
  作者：Ronald N. Warrener、Davor Margetic、Patrick J. Foley、Douglas N. Butler、Alain Winling、Kerry A. Beales、Richard A. Russell

  DOI：10.1016/s0040-4020(00)01027-9

  日期：2001.1

  syn-facial N,O-bridged polynorbornanes and stereorandomly with 7-oxanorbornenes to produce O,O-bridged polynorbornanes as mixtures of syn-facial and anti-facial products. 1 Polarofacial systems containing up to six syn-facial norbornane bridges are described, while systems with seven co-facial oxygen atoms have been prepared by incorporating terminal epoxide rings to O5-[5]polynorbornanes. Ester-substituted

  新氧桥降冰片烷-稠合环丁烯环氧化物和双- （环丁烯环氧化物）中描述和示出为7-azanorbornenes以产生立体选择性反应顺式-facial Ñ，ö -bridged polynorbornanes和stereorandomly 7-oxanorbornenes以产生ö，ö -桥接polynorbornanes作为混合物顺式-facial和抗-facial产品。1个含有多达六个Polarofacial系统SYN -facial降冰片烷桥描述的，当具有七个共面的氧原子系统已经制备通过将末端环氧环至O 5-[5]聚降冰片烷。酯取代的1,3,4-恶二唑被示出为是有用的试剂，用于耦合7- oxanorbornanes和主要产生顺-facial ö -bridged polarofacial与它们一起系统抗-facial异构体。
• The 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Coupling of Norbornenes and 7-Oxanorbornenes under High Pressure: New Structures, Mechanistic Detail and Synthetic Applications
  作者：Ronald Warrener、Davor Margetic、Edward Tiekink、Richard Russell

  DOI：10.1055/s-1997-738

  日期：1997.2

  A comparison of reactivities, site selectivities, calculation and thermal versus high pressure (14 kbar) reaction conditions are used in a study of the coupling of bicyclic alkenes with 1,3,4-oxadiazoles (and 1,3,4-thiadiazoles) which sets the boundary conditions for such coupling and identifies a 1,3-dipolar species as the likely intermediate.

  在双环烯烃与 1,3,4-恶二唑（和 1,3,4-噻二唑）偶联的研究中使用了反应性、位点选择性、计算以及热与高压（14 kbar）反应条件的比较，其中设置这种耦合的边界条件并确定 1,3-偶极物质作为可能的中间体。
• Intramolecular Diels−Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles
  作者：Gregory I. Elliott、James R. Fuchs、Brian S. J. Blagg、Hayato Ishikawa、Houchao Tao、Z.-Q. Yuan、Dale L. Boger

  DOI：10.1021/ja0612549

  日期：2006.8.1

  Full details of a systematic exploration of the intramolecular [4+2]/[3+2] cycloaddition cascade of 1,3,4-oxadiazoles are disclosed in which the scope and utility of the reaction are defined.
• Reaction of 2,5-bis-trifluoromethyl-1,3,4-oxadiazole with 7-oxanorbornenes revisited: Experimental and quantum-chemical study of reaction stereoselectivity
  作者：Davor Margetić、Mirjana Eckert-Maksić、Pavle Trošelj、Željko Marinić

  DOI：10.1016/j.jfluchem.2009.12.012

  日期：2010.3

  The stereochemical outcome of reaction of 2,5-bis-trifluoromethyl-1,3,4-oxadiazole with 7-oxanorbornenes under various conditions was investigated. For the first time, microwave irradiation in carrying this type of reactions was used, resulting in comparable yields in significantly shorter reaction times. Regardless on substrate, in all reactions mixtures of the two isomeric O-3-[3]polynorbornanes, bent and linear were obtained, with slight preference for bent structure. In some cases, retro Diels-Alder fragmentation was observed resulting in formation of isobenzofuran species. Reaction mechanism was also studied computationally (RHF/6-31G* method), and the origin of stereoselectivity explained by repulsive lone pair interactions between oxygen bridges in the transition state of the 1,3-dipolar addition. (C) 2009 Elsevier B.V. All rights reserved.
• THALHAMMER, FRANZ;WALLFAHRER, UWE;SAUER, JURGEN, TETRAHEDRON. LETT., 29,(1988) N 26, 3231-3234
  作者：THALHAMMER, FRANZ、WALLFAHRER, UWE、SAUER, JURGEN

  DOI：——

  日期：——