1,3,5-Tris-benzyloxy-2-bromo-benzene | 886204-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3,5-Tris-benzyloxy-2-bromo-benzene
• 英文别名: 2-Bromo-1,3,5-tris(phenylmethoxy)benzene
• CAS: 886204-61-1
• 化学式: C₂₇H₂₃BrO₃
• 分子量: 475.382
• InChiKey: HOYGSGOIMFXNND-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96 °C(Solv: methanol (67-56-1))
• 沸点：
  597.2±45.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-Tris-benzyloxy-2-bromo-benzene 在 N-溴代丁二酰亚胺(NBS) 、 18-冠醚-6 、 三氟化硼乙醚 、 potassium hydride 、 镍 、 碳酸氢钠 、 potassium carbonate 、 氟化氢吡啶 、 苯基锂 、 苯硫酚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， -78.0~50.0 ℃ 、413.68 kPa 条件下， 反应 51.38h， 生成 epi-calyxin F
  参考文献：
  名称：

  Synthesis and Structure Revision of Calyxin Natural Products

  摘要：

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.

  DOI：

  10.1021/jo060094g
• 作为产物：
  描述：

  1,3,5-三(苯基甲氧基)苯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到1,3,5-Tris-benzyloxy-2-bromo-benzene
  参考文献：
  名称：

  Synthesis and Structure Revision of Calyxin Natural Products

  摘要：

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.

  DOI：

  10.1021/jo060094g

文献信息

• (±)-Diinsininone: made nature's way
  作者：Carolyn Selenski、Thomas R.R. Pettus

  DOI：10.1016/j.tet.2006.01.109

  日期：2006.5

  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.