Carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester | 895918-10-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: Carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester
• CAS: 895918-10-2
• 化学式: C₂₇H₃₆O₇Si
• 分子量: 500.664
• InChiKey: WQYLGMZWGJAVPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester 、 phenylmagnesium bromide 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以52%的产率得到
  参考文献：
  名称：

  (±)-Diinsininone: made nature's way

  摘要：

  We report the synthesis of diinsininone (33), the aglycone of (+/-)-diinsinin (2). Thereby, we complete the first construction of a proamhocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective beta-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.109
• 作为产物：
  描述：

  5-羟基-2-(4-羟基苯基)-7-甲氧基-2,3-二氢-4H-苯并吡喃-4-酮 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 Carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester
  参考文献：
  名称：

  (±)-Diinsininone: made nature's way

  摘要：

  We report the synthesis of diinsininone (33), the aglycone of (+/-)-diinsinin (2). Thereby, we complete the first construction of a proamhocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective beta-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.109