| 524674-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 524674-84-8
• 化学式: C₄₄H₆₆O₃₆S₂
• 分子量: 1235.12
• InChiKey: YJRVZCWHEMKWPT-NVIADHKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.9
• 重原子数：
  82.0
• 可旋转键数：
  6.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  539.64
• 氢给体数：
  16.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到
  参考文献：
  名称：

  Goodness of Fit in Complexes between Substrates and Ribonuclease Mimics:  Effects on Binding, Catalytic Rate Constants, and Regiochemistry

  摘要：

  The hydrolysis of 4-tert-butylcatechol cyclic phosphate and of 4-methylcatechol cyclic phosphate catalyzed by alpha-cyclodextrin-6A,6B-bisimidazolide, and by the corresponding derivatives of beta-cyclodextrin (beta CD) and gamma-cyclodextrin (gamma CD), was examined, All three catalysts were able to hydrolyze the substrate derived from 4-methylcatechol, but only the beta CD- and gamma CD-based catalysts could hydrolyze the substrate based on 4-tert-butylcatechol. Saturation kinetics were observed, from which k(cat) and K-m values were derived. The k(cat)'s showed a bell-shaped dependence on pH, indicating a bifunctional mechanism in which one imidazole acted as a base while the other, protonated, acted as an acid catalyst. The strongest binding was observed between the substrate derived from tert-butylcatechol and the beta CD-based catalyst, and this combination also had the highest k(cat), An Arrhenius plot showed that the good fit of the tert-butyl group into the beta CD cavity leads to an entropy advantage for catalysis within the complex, as well as an advantage in the binding. Furthermore, the combination with the best binding and catalytic constant also exhibited the highest regioselectivity in the substrate hydrolysis, being essentially completely selective for one mode of hydrolysis. All these effects reflect the result of a tight fit of the substrate into the catalyst binding cavity, leading to a well-defined reaction geometry.

  DOI：

  10.1021/ja954307n
• 作为产物：
  描述：

  4,6-二甲氧基-1,3-苯二磺酰基二氯化物 、 α-环糊精 在 吡啶 作用下， 反应 3.0h， 以2.3%的产率得到
  参考文献：
  名称：

  Goodness of Fit in Complexes between Substrates and Ribonuclease Mimics:  Effects on Binding, Catalytic Rate Constants, and Regiochemistry

  摘要：

  The hydrolysis of 4-tert-butylcatechol cyclic phosphate and of 4-methylcatechol cyclic phosphate catalyzed by alpha-cyclodextrin-6A,6B-bisimidazolide, and by the corresponding derivatives of beta-cyclodextrin (beta CD) and gamma-cyclodextrin (gamma CD), was examined, All three catalysts were able to hydrolyze the substrate derived from 4-methylcatechol, but only the beta CD- and gamma CD-based catalysts could hydrolyze the substrate based on 4-tert-butylcatechol. Saturation kinetics were observed, from which k(cat) and K-m values were derived. The k(cat)'s showed a bell-shaped dependence on pH, indicating a bifunctional mechanism in which one imidazole acted as a base while the other, protonated, acted as an acid catalyst. The strongest binding was observed between the substrate derived from tert-butylcatechol and the beta CD-based catalyst, and this combination also had the highest k(cat), An Arrhenius plot showed that the good fit of the tert-butyl group into the beta CD cavity leads to an entropy advantage for catalysis within the complex, as well as an advantage in the binding. Furthermore, the combination with the best binding and catalytic constant also exhibited the highest regioselectivity in the substrate hydrolysis, being essentially completely selective for one mode of hydrolysis. All these effects reflect the result of a tight fit of the substrate into the catalyst binding cavity, leading to a well-defined reaction geometry.

  DOI：

  10.1021/ja954307n

文献信息

• An efficient strategy for the modification of α-cyclodextrin: direct conversion of one or two adjacent 6-OHs to phthalimides
  作者：De-Qi Yuan、Cheng Yang、Tarou Fukuda、Kahee Fujita

  DOI：10.1016/s0040-4039(02)02503-0

  日期：2003.1

  alpha-Cyclodextrin was reacted with phthalimide under modified Mitsunobu conditions to give the 6(A)-deoxy-6(A)-phthalimido-alpha-cyclodextrin in 41% yield. This reaction also worked well in the modification of two methylene carbons, giving the 6(A),6(B)-, 6(A),6(C)- and 6(A),6(D)-diphthalimido-alpha-cyclodextrins in 22, 9.5 and 4.6% isolated yields, respectively. All the phthalimido species can be quantitatively converted to the corresponding amino cyclodextrins by hydrazinolysis. (C) 2002 Elsevier Science Ltd. All rights reserved.