2,4-bis(tert-butyldiphenylsilyloxy)benzaldehyde | 1141854-11-6

• 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: 2,4-bis(tert-butyldiphenylsilyloxy)benzaldehyde
• 英文别名: 2,4-Bis[[tert-butyl(diphenyl)silyl]oxy]benzaldehyde
• CAS: 1141854-11-6
• 化学式: C₃₉H₄₂O₃Si₂
• 分子量: 614.932
• InChiKey: WSPGRMWYMUGDIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.38
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-bis(tert-butyldiphenylsilyloxy)benzaldehyde 在 10 wt% Pd(OH)2 on carbon 、 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 为溶剂， 反应 10.0h， 生成 dihydrooxyresveratrol
  参考文献：
  名称：

  Molecular design of potent, hydrophilic tyrosinase inhibitors based on the natural dihydrooxyresveratrol skeleton

  摘要：

  In this study, dihydrooxyresveratrol glucosides 3-6 were synthesized for the first time to the best of our knowledge by the Wittig reaction and Schmidt glycosylation as key steps for the purpose of developing novel hydrophilic tyrosinase inhibitors. Results obtained from inhibitory studies revealed 50% inhibitory concentration (IC50) values of 12.80 mu M and 2.63 mu M for 4-resorcinol glucosides 3 and 4, respectively. The IC50 value of 4 was approximately 4 times greater than that of kojic acid, which is a typical tyrosinase inhibitor. In contrast, 5-resorcinol glucosides 5 and 6 exhibited tyrosinase-inhibitory activity; however their IC(50)s were not estimated within 100 mu M. These results suggested that the discovering 4-resorcinol structure of dihydrooxyresveratrol glucoside is crucial for inducing potent tyrosinase-inhibitory activity.

  DOI：

  10.1016/j.carres.2018.11.006
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 2,4-二羟基苯甲醛 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以83%的产率得到2,4-bis(tert-butyldiphenylsilyloxy)benzaldehyde
  参考文献：
  名称：

  努力实现细菌肽去甲酰基化酶（PDF）抑制剂富米霉素的不对称合成† ‡

  摘要：

  报道了合成细菌肽去甲酰基化酶（PDF）抑制剂富米霉素的研究。合成方法的特征是有机催化接近α，α-二取代的氨基酸单元，并导致合成高级中间体，该中间体已经包含了泛霉素的所有功能。

  DOI：

  10.1039/b916372g

文献信息

• Towards an asymmetric synthesis of the bacterial peptide deformylase (PDF) inhibitor fumimycin
  作者：Caroline E. Hartmann、Patrick J. Gross、Martin Nieger、Stefan Bräse

  DOI：10.1039/b916372g

  日期：——

  Studies towards the synthesis of the bacterial peptide deformylase (PDF) inhibitor fumimycin are reported. The synthetic approach features an organocatalytic access to the α,α-disubstituted amino acid unit and results in the synthesis of an advanced intermediate which already contains all functionalities of fumimycin.

  报道了合成细菌肽去甲酰基化酶（PDF）抑制剂富米霉素的研究。合成方法的特征是有机催化接近α，α-二取代的氨基酸单元，并导致合成高级中间体，该中间体已经包含了泛霉素的所有功能。
• Molecular design of potent, hydrophilic tyrosinase inhibitors based on the natural dihydrooxyresveratrol skeleton
  作者：Yuri Tanaka、Marina Suzuki、Yuka Kodachi、Ken-ichi Nihei

  DOI：10.1016/j.carres.2018.11.006

  日期：2019.1

  In this study, dihydrooxyresveratrol glucosides 3-6 were synthesized for the first time to the best of our knowledge by the Wittig reaction and Schmidt glycosylation as key steps for the purpose of developing novel hydrophilic tyrosinase inhibitors. Results obtained from inhibitory studies revealed 50% inhibitory concentration (IC50) values of 12.80 mu M and 2.63 mu M for 4-resorcinol glucosides 3 and 4, respectively. The IC50 value of 4 was approximately 4 times greater than that of kojic acid, which is a typical tyrosinase inhibitor. In contrast, 5-resorcinol glucosides 5 and 6 exhibited tyrosinase-inhibitory activity; however their IC(50)s were not estimated within 100 mu M. These results suggested that the discovering 4-resorcinol structure of dihydrooxyresveratrol glucoside is crucial for inducing potent tyrosinase-inhibitory activity.