(Z)-5-azido-3-cyclohexenecarboxylic acid

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (Z)-5-azido-3-cyclohexenecarboxylic acid
• 英文别名: Rac-(1r,5r)-5-azidocyclohex-3-ene-1-carboxylic acid；(1R,5R)-5-azidocyclohex-3-ene-1-carboxylic acid
• 化学式: C₇H₉N₃O₂
• 分子量: 167.167
• InChiKey: LTUSSIYFBSMQDT-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-5-azido-3-cyclohexenecarboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以94%的产率得到((1R,5R)-5-Amino-cyclohex-3-enyl)-methanol
  参考文献：
  名称：

  Synthesis and Biological Activity of Cyclohexenyl Nucleosides.cis-5-(9H-Purin-9-yl)-3-cyclohexenyl Carbinols and Their 8-Azapurinyl Analogs

  摘要：

  5-Azido-3-cyclohexenecarboxylic acid was reduced to an aminocyclohexenylcarbinol which was coupled with either 5-amino-4,6-dichloropyrimidine or 2-amino-4,6-dichloropyrimidine, giving 5-pyrimidinyl-3-cyclohexencarbinols. Condensation with triethylorthoformate or nitrous acid formed the purine and 8-azapurine ring systems, respectively. Anti-HIV-1 and cytotoxicity testing results are also described.

  DOI：

  10.1080/15257779508010724
• 作为产物：
  描述：

  6-氧杂双环[3.2.1]辛-3-烯-7-酮 在 sodium azide 、 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以92%的产率得到(Z)-5-azido-3-cyclohexenecarboxylic acid
  参考文献：
  名称：

  Palladium(0)-catalyzed azidation of allyl esters. Selective synthesis of allyl azides, primary allylamines, and related compounds

  摘要：

  DOI：

  10.1021/jo00275a011

文献信息

• MURAHASHI, SHUN-ICHI;TANIGUCHI, YUKI;IMADA, YASUSHI;TANIGAWA, YOSHIO, J. ORG. CHEM., 54,(1989) N4, C. 3292-3303
  作者：MURAHASHI, SHUN-ICHI、TANIGUCHI, YUKI、IMADA, YASUSHI、TANIGAWA, YOSHIO

  DOI：——

  日期：——
• Palladium(0)-catalyzed azidation of allyl esters. Selective synthesis of allyl azides, primary allylamines, and related compounds
  作者：Shunichi Murahashi、Yuki Taniguchi、Yasushi Imada、Yoshio Tanigawa

  DOI：10.1021/jo00275a011

  日期：1989.7
• Synthesis and Biological Activity of Cyclohexenyl Nucleosides.<i>cis</i>-5-(9<i>H</i>-Purin-9-yl)-3-cyclohexenyl Carbinols and Their 8-Azapurinyl Analogs
  作者：Michael J. Konkel、Robert Vince

  DOI：10.1080/15257779508010724

  日期：1995.11

  5-Azido-3-cyclohexenecarboxylic acid was reduced to an aminocyclohexenylcarbinol which was coupled with either 5-amino-4,6-dichloropyrimidine or 2-amino-4,6-dichloropyrimidine, giving 5-pyrimidinyl-3-cyclohexencarbinols. Condensation with triethylorthoformate or nitrous acid formed the purine and 8-azapurine ring systems, respectively. Anti-HIV-1 and cytotoxicity testing results are also described.