1,1-bis[4-(N,N′-di(tert-butoxycarbonyl)guanidinephenyl)]cyclohexane | 1443793-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-bis[4-(N,N′-di(tert-butoxycarbonyl)guanidinephenyl)]cyclohexane
• 英文别名: tert-butyl N-[N'-[4-[1-[4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]phenyl]cyclohexyl]phenyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 1443793-79-0
• 化学式: C₄₀H₅₈N₆O₈
• 分子量: 750.936
• InChiKey: GFCHGSOIRHEQOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,1-bis[4-(N,N′-di(tert-butoxycarbonyl)guanidinephenyl)]cyclohexane 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以97%的产率得到1,1-bis[4-(guanidinephenyl)]cyclohexane bishydrochloride
  参考文献：
  名称：

  Guanidine–Guanidinium Cooperation in Bifunctional Artificial Phosphodiesterases Based on Diphenylmethane Spacers; gem-Dialkyl Effect on Catalytic Efficiency

  摘要：

  Diphenylmethane derivatives 1-3, decorated with two guanidine units, are effective catalysts of HPNP transesterification. Substitution of the methylene group of the parent diphenylmethane spacer with cyclohexylidene and adamantylidene moieties enhances catalytic efficency, with gem-dialkyl effect accelerations of 4.5 and 9.1, respectively. Activation parameters and DFT calculations of the rotational barriers around the C-Ar bonds indicate that a major contribution to the driving force for enhanced catalysis is entropic in nature.

  DOI：

  10.1021/jo401085z
• 作为产物：
  描述：

  1,1-双(4-氨基苯基)环己烷 、 N,N′-二-Boc-硫脲 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以52%的产率得到1,1-bis[4-(N,N′-di(tert-butoxycarbonyl)guanidinephenyl)]cyclohexane
  参考文献：
  名称：

  Guanidine–Guanidinium Cooperation in Bifunctional Artificial Phosphodiesterases Based on Diphenylmethane Spacers; gem-Dialkyl Effect on Catalytic Efficiency

  摘要：

  Diphenylmethane derivatives 1-3, decorated with two guanidine units, are effective catalysts of HPNP transesterification. Substitution of the methylene group of the parent diphenylmethane spacer with cyclohexylidene and adamantylidene moieties enhances catalytic efficency, with gem-dialkyl effect accelerations of 4.5 and 9.1, respectively. Activation parameters and DFT calculations of the rotational barriers around the C-Ar bonds indicate that a major contribution to the driving force for enhanced catalysis is entropic in nature.

  DOI：

  10.1021/jo401085z

文献信息

• Guanidine–Guanidinium Cooperation in Bifunctional Artificial Phosphodiesterases Based on Diphenylmethane Spacers; <i>gem</i>-Dialkyl Effect on Catalytic Efficiency
  作者：Riccardo Salvio、Luigi Mandolini、Claudia Savelli

  DOI：10.1021/jo401085z

  日期：2013.7.19

  Diphenylmethane derivatives 1-3, decorated with two guanidine units, are effective catalysts of HPNP transesterification. Substitution of the methylene group of the parent diphenylmethane spacer with cyclohexylidene and adamantylidene moieties enhances catalytic efficency, with gem-dialkyl effect accelerations of 4.5 and 9.1, respectively. Activation parameters and DFT calculations of the rotational barriers around the C-Ar bonds indicate that a major contribution to the driving force for enhanced catalysis is entropic in nature.