(E)-3-azido-but-2-enoic acid methyl ester | 81777-19-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3-azido-but-2-enoic acid methyl ester
• 英文别名: (E)-3-azidobut-2-enoic acid methyl ester；methyl (E)-3-azidobut-2-enoate；E-methyl 3-azidocrotonate；Methyl 3-azidocrotonate
• CAS: 81777-19-7
• 化学式: C₅H₇N₃O₂
• 分子量: 141.129
• InChiKey: BHANTFZXBXWERG-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 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：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-azido-but-2-enoic acid methyl ester 以 二氯甲烷 、 氯仿 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Preparation and reactivity of electron-poor 2-azadienes. Diels-Alder reaction with trans-cyclooctene.

  摘要：

  Di-, tri- and tetra- substituted 2-azadienes 3 underbar with electron withdrawing groups have been obtained by Aza-Wittig reaction of N-vinylic phosphazenes with carbonyl compounds. The Diels-Alder reaction of 3 underbar with trans-cyclooctene has also been explored.

  DOI：

  10.1016/s0040-4039(00)79357-9
• 作为产物：
  描述：

  2,3-丁二烯酸甲酯 在 tetramethylguanidinum azide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以68%的产率得到(E)-3-azido-but-2-enoic acid methyl ester
  参考文献：
  名称：

  Palacios, F.; Aparicio, D.; Santos, J. M. de los, Organic Preparations and Procedures International, 1995, vol. 27, # 2, p. 171 - 178

  摘要：

  DOI：

文献信息

• Total Synthesis of (+)-Batzelladine A and (−)-Batzelladine D via [4 + 2]-Annulation of Vinyl Carbodiimides with <i>N</i>-Alkyl Imines
  作者：Michael A. Arnold、Kenneth A. Day、Sergio G. Durón、David Y. Gin

  DOI：10.1021/ja063860+

  日期：2006.10.1

  this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol.

  已经开发出乙烯基碳二亚胺与手性 N-烷基亚胺的非对映选择性 [4 + 2]-环化，以获取 batzelladine 生物碱的立体化学丰富的多环胍核。该策略的应用，连同其他关键步骤，如远程定向氢化和非对映选择性分子内碘胺化，导致 (-)-batzelladine D 和 (+)-batzelladine A 的高度收敛全合成具有出色的立体控制。
• Diastereoselective [4+2] Annulation of Vinyl Carbodiimides with <i>N</i>-Alkyl Imines. Asymmetric Synthetic Access to the Batzelladine Alkaloids
  作者：Michael A. Arnold、Sergio G. Durón、David Y. Gin

  DOI：10.1021/ja0519029

  日期：2005.5.1

  diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich tricyclic core of the batzelladine alkaloids. Its application to the asymmetric synthesis of batzelladine D permitted the use of long-range, directed hydrogenation and stereoselective intramolecular iodoamination as additional key steps to establish the remaining stereocenters

  已经开发出乙烯基碳二亚胺与手性 N-烷基亚胺的非对映选择性 [4+2] 环化，以获取巴泽拉定生物碱的立体化学丰富的三环核心。其在 batzelladine D 的不对称合成中的应用允许使用长程、定向氢化和立体选择性分子内碘胺化作为额外的关键步骤，以在具有出色立体控制的天然产物中建立剩余的立体中心。
• Cambie, Richard C.; Jurlina, Jeffrey L.; Rutledge, Peter S., Journal of the Chemical Society. Perkin transactions I, 1982, p. 327 - 334
  作者：Cambie, Richard C.、Jurlina, Jeffrey L.、Rutledge, Peter S.、Swedlund, Bernard E.、Woodgate, Paul D.

  DOI：——

  日期：——
• Synthesis and Reactivity of Electron-Poor 2-Azadienes. [4 + 2] Cycloaddition Reactions with Alkenes and Enamines
  作者：Francisco Palacios、Itziar Perez de Heredia、Gloria Rubiales

  DOI：10.1021/jo00113a017

  日期：1995.4

  Electron deficient 2-azadienes derived from beta-amino acids 3 are obtained by aza-Wittig reaction of N-vinylic phosphazenes 4 with carbonyl compounds. Inverse electron demand Diels-Alder reaction of azadienes 3 with trans-cyclooctene 7 and cis,trans-cyclooctadiene 8 leads to the formation of trans-cycloalkanotetrahydropyridines 10. Heterodienes 3 also react with enamines 13, 14, and 18 affording pyridine derivatives 16, 17, and 20 in a regioselective fashion. Norbornadiene 11, a less strained olefin than cycloalkenes 7 and 8, requires the presence of lithium perchlorate as catalyst in a nonaqueous solvent like ether, to give cycloadducts 12.
• CAMBIE, R. C.;JURLINA, J. L.;RUTLEDGE, P. S.;SWEDLUND, B. E.;WOODGATE, P.+, J. CHEM. SOC. PERKIN TRANS., 1982, N 2, 327-333
  作者：CAMBIE, R. C.、JURLINA, J. L.、RUTLEDGE, P. S.、SWEDLUND, B. E.、WOODGATE, P.+

  DOI：——

  日期：——