(1S*,2S*)-cyclohex-4-ene-1,2-dicarbohydrazide | 14246-80-1

• 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: (1S*,2S*)-cyclohex-4-ene-1,2-dicarbohydrazide
• 英文别名: (+/-)-trans-cyclohex-4-ene-1,2-dicarboxylic acid dihydrazide；(+/-)-trans-Cyclohex-4-en-1,2-dicarbonsaeure-dihydrazid；(1S,2S)-cyclohex-4-ene-1,2-dicarbohydrazide
• CAS: 14246-80-1；99938-57-5；105249-38-5；118157-52-1
• 化学式: C₈H₁₄N₄O₂
• 分子量: 198.225
• InChiKey: FJFRLOOYFSNNQZ-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S*,2S*)-cyclohex-4-ene-1,2-dicarbohydrazide 在 盐酸 、 sodium nitrite 作用下， 生成 rac-(trans)-cyclohex-4-ene-1,2-diamine dihydrochloride
  参考文献：
  名称：

  Synthesis of [3H2]-(R,R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [3H2]-Oxaliplatin

  摘要：

  A synthesis of [H-3(2)]-(R, R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [H-3(2)-Oxaliplatin, 2, is described. rac-trans-4-Cyclohexene-1,2-dicarboxylic acid diethyl ester, 6, was converted to rac-trans-1,2-diaminocyclohex-4-ene, 7, by modification of known chemistry aimed at avoiding reported hazards. Resolution of the diamine, 7, with L-(+)-tartaric acid afforded the (R,R)-1,2-diaminocyclohex-4-ene, 8, which was converted to the (R,R)-1,2-bis(tert-butoxycarbamino)cyclohex-4-ene, 10, and tritiated to yield [H-3(2)-(R,R)-1,2-bis(tert-butoxycarbamino)cyclohexane, 11. Hydrolysis of 11 afforded [H-3(2)]-(R,R)-1,2-diaminacyclohexane, 12, which was converted to the desired [H-3(2)]-(R,R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [H-3(2)]-Oxaliplatin, 2.

  DOI：

  10.1002/(sici)1099-1344(199805)41:5<443::aid-jlcr100>3.0.co;2-w
• 作为产物：
  描述：

  trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene 在 一水合肼 作用下， 反应 8.0h， 以68%的产率得到(1S*,2S*)-cyclohex-4-ene-1,2-dicarbohydrazide
  参考文献：
  名称：

  Synthesis of [3H2]-(R,R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [3H2]-Oxaliplatin

  摘要：

  A synthesis of [H-3(2)]-(R, R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [H-3(2)-Oxaliplatin, 2, is described. rac-trans-4-Cyclohexene-1,2-dicarboxylic acid diethyl ester, 6, was converted to rac-trans-1,2-diaminocyclohex-4-ene, 7, by modification of known chemistry aimed at avoiding reported hazards. Resolution of the diamine, 7, with L-(+)-tartaric acid afforded the (R,R)-1,2-diaminocyclohex-4-ene, 8, which was converted to the (R,R)-1,2-bis(tert-butoxycarbamino)cyclohex-4-ene, 10, and tritiated to yield [H-3(2)-(R,R)-1,2-bis(tert-butoxycarbamino)cyclohexane, 11. Hydrolysis of 11 afforded [H-3(2)]-(R,R)-1,2-diaminacyclohexane, 12, which was converted to the desired [H-3(2)]-(R,R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [H-3(2)]-Oxaliplatin, 2.

  DOI：

  10.1002/(sici)1099-1344(199805)41:5<443::aid-jlcr100>3.0.co;2-w

文献信息

• Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure
  作者：Zeynep Ekmekci、Metin Balci

  DOI：10.1002/ejoc.201200582

  日期：2012.9

  of the double bond in the six-membered ring followed by a DBU-induced (DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene) HBr elimination furnished the symmetrical diene. The photooxygenation of the diene unit afforded the bicyclic endoperoxide. The reaction of the endoperoxide with thiourea followed by acetylation resulted in the formation of a syn-configured diacetate. The deprotection of the urethane and acetate

  以环己-1,4-二烯为原料制备了一种新的具有 conduritol F 结构的 2,3-diaminoconduritol 衍生物。最初，通过氯磺酰基异氰酸酯 (CSI) 与环己-1,4-二烯的环加成反应制备的内酰胺转化为氨基酸。酸官能团转化为异氰酸酯导致形成咪唑烷酮衍生物，通过分子内环化形成。在这项工作的第二部分，已知的酸酐，3a,4,7,7a-四氢异苯并呋喃-1,3-二酮被成功转化为所需的双（氨基甲酸酯）。六元环中双键的溴化，然后是 DBU 诱导的（DBU = 1,8-二氮杂双环 [5.4.0] undec-7-ene）HBr 消除提供了对称的二烯。二烯单元的光氧化提供双环内过氧化物。内过氧化物与硫脲的反应随后乙酰化导致形成顺式构型的二乙酸酯。氨基甲酸酯和乙酸酯基团的脱保护得到具有 conduritol F 结构的新 2,3-diaminoconduritol。
• Jaschunskii et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2712,2717; engl. Ausg. S. 2680, 2684
  作者：Jaschunskii et al.

  DOI：——

  日期：——
• Synthesis of [3H2]-(R,R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [3H2]-Oxaliplatin
  作者：Alain Burgos、George J. Ellames

  DOI：10.1002/(sici)1099-1344(199805)41:5<443::aid-jlcr100>3.0.co;2-w

  日期：1998.5

  A synthesis of [H-3(2)]-(R, R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [H-3(2)-Oxaliplatin, 2, is described. rac-trans-4-Cyclohexene-1,2-dicarboxylic acid diethyl ester, 6, was converted to rac-trans-1,2-diaminocyclohex-4-ene, 7, by modification of known chemistry aimed at avoiding reported hazards. Resolution of the diamine, 7, with L-(+)-tartaric acid afforded the (R,R)-1,2-diaminocyclohex-4-ene, 8, which was converted to the (R,R)-1,2-bis(tert-butoxycarbamino)cyclohex-4-ene, 10, and tritiated to yield [H-3(2)-(R,R)-1,2-bis(tert-butoxycarbamino)cyclohexane, 11. Hydrolysis of 11 afforded [H-3(2)]-(R,R)-1,2-diaminacyclohexane, 12, which was converted to the desired [H-3(2)]-(R,R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [H-3(2)]-Oxaliplatin, 2.