4-(4-allyloxyphenylcarboxy)benzaldehyde | 146028-57-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(4-allyloxyphenylcarboxy)benzaldehyde
• 英文别名: (4-Formylphenyl) 4-prop-2-enoxybenzoate
• CAS: 146028-57-1
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: NNSHWWJZAJGKFR-UHFFFAOYSA-N

物化性质

• 沸点：
  457.3±35.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1,3-苯并噻唑-2-基)苯酚 、 4-(4-allyloxyphenylcarboxy)benzaldehyde 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 以73%的产率得到4-(benzo[d]thiazol-2-yl)phenyl 4-(allyloxy)benzoate
  参考文献：
  名称：

  2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms

  摘要：

  The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 mu g/ml; MIC(LORA) 2.06 and 1.59 mu g/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 mu M respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 mu M respectively) followed by the Vit-K2 rescue study and ATP production assay.

  DOI：

  10.1016/j.bioorg.2020.104170
• 作为产物：
  描述：

  4-(烯丙氧基)苯甲酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 4-(4-allyloxyphenylcarboxy)benzaldehyde
  参考文献：
  名称：

  2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms

  摘要：

  The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 mu g/ml; MIC(LORA) 2.06 and 1.59 mu g/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 mu M respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 mu M respectively) followed by the Vit-K2 rescue study and ATP production assay.

  DOI：

  10.1016/j.bioorg.2020.104170

文献信息

• Substituent effects on the enantioselective hydrocyanation of aryl aldehydes
  作者：Hyun J. Kim、W.Roy Jackson

  DOI：10.1016/0957-4166(94)80124-x

  日期：1994.8

  A detailed study of the dipeptide catalysed enantioselective hydrocyanation of a series of O-substituted 4-hydroxybenzaldehydes has shown that adverse steric effects can occur leading to low enantiomeric excess (e.e.) values when the substituent is long and flexible. Similar hydrocyanation of several derivatives of 3,4-dihydroxybenzaldehydes have been shown to give very variable values of e.e. Hydrocyanation of 3,5-dimethoxy and 3,4,5-trimethoxybenzaldehyde consistently gave low values of e.e.
• Polymer attached cyclic dipeptides as catalysts for enantioselective cyanohydrin formation
  作者：Hyun J. Kim、W.Roy Jackson

  DOI：10.1016/0957-4166(92)80019-s

  日期：1992.11

  Derivatives of cyclo-[(S)-Tyr-(S)-His], related to the 'Inoue' catalyst, cyclo-[(S)-Phe-(S)-His] have been attached to chloromethylated polystyrene and to polysiloxane polymers via spacer groups coupled to the tyrosine phenolic residue. These polymer-attached dipeptides have been shown to be efficient catalysts for the conversion of aromatic aldehydes to cyanohydrins but enantioselectivities are low. The loss of enantioselectivity relative to the Inoue catalyst has been attributed to steric effects from the substituents on the tyrosyl phenolic group. Some mechanistic comments regarding the preferred conformation of the active dipeptide are made.
• 2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms
  作者：Anand Babu Velappan、Dhrubajyoti Datta、Rui Ma、Shiwani Rana、Kalyan Sundar Ghosh、Natarajan Hari、Scott G. Franzblau、Joy Debnath

  DOI：10.1016/j.bioorg.2020.104170

  日期：2020.10

  The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 mu g/ml; MIC(LORA) 2.06 and 1.59 mu g/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 mu M respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 mu M respectively) followed by the Vit-K2 rescue study and ATP production assay.