Tert-butyl 4-formyl-3,5-bis(phenylmethoxy)benzoate | 177956-46-6

• 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: Tert-butyl 4-formyl-3,5-bis(phenylmethoxy)benzoate
• CAS: 177956-46-6
• 化学式: C₂₆H₂₆O₅
• 分子量: 418.489
• InChiKey: HYVWUYNDMQKCGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-formyl-3,5-bis(phenylmethoxy)benzoate 在 palladium on carbon 、 氢气 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 以48%的产率得到tert-butyl (3-benzyloxy)-4-formyl-5-hydroxybenzoate
  参考文献：
  名称：

  Aziridinomitosanes via Lactam Cyclization

  摘要：

  Aziridinomitosane ketones 4 and 24 are accessed by internal acyl anion equivalent-lactam cyclization of 29 in a convergent route. The key aziridinolactam 6 is prepared by tin lithium exchange via the lithiated aziridine 11.

  DOI：

  10.1021/ol101595u
• 作为产物：
  描述：

  4-溴-3,5-二羟基苯甲酸 在 sodium hydroxide 、 正丁基锂 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.67h， 生成 Tert-butyl 4-formyl-3,5-bis(phenylmethoxy)benzoate
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Balanol¹

  摘要：

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.

  DOI：

  10.1021/jo952280k

文献信息

• Ring Formylation of Bromobenzoate Esters by Direct Metalation
  作者：Andrew S. Kende、Min Zhong

  DOI：10.1080/00397919908085967

  日期：1999.10

  A study on the synthesis of a benzaldehyde containing an ester function directly from tert-butyl 4-lithiobenzate was described. t-Butyl 4-bromobenzoate reacted with butyllithium at -78 degrees C in THF, followed by immediate addition of DMF to give the desired benzaldehyde in moderate yield. The scope of this reaction was examined.
• Total Synthesis of (−)- and (+)-Balanol¹
  作者：John W. Lampe、Philip F. Hughes、Christopher K. Biggers、Shelley H. Smith、Hong Hu

  DOI：10.1021/jo952280k

  日期：1996.1.1

  Two total syntheses of the potent protein kinase C inhibitory fungal metabolite balanol are described. In the first approach, the core aminohydroxyazepane subunit was prepared in racemic form by stereospecific functionalization of N-benzyl-epsilon-caprolactam. Resolution prior to coupling to the benzophenone subunit provided access to both enantiomers of balanol. In the second approach, an efficient silicon-mediated cyclization of(2S,3R)-3-hydroxylysine followed by reduction provided the azepane subunit in enantiomerically pure form. The sterically congested benzophenone subunit was assembled from two highly substituted aromatic precursors by way of an anionic home-Fries rearrangement.
• Aziridinomitosanes via Lactam Cyclization
  作者：Susan D. Wiedner、Edwin Vedejs

  DOI：10.1021/ol101595u

  日期：2010.9.17

  Aziridinomitosane ketones 4 and 24 are accessed by internal acyl anion equivalent-lactam cyclization of 29 in a convergent route. The key aziridinolactam 6 is prepared by tin lithium exchange via the lithiated aziridine 11.