5-bromo-3,4-dibenzyloxybenzaldehyde | 124662-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-3,4-dibenzyloxybenzaldehyde
• 英文别名: 3,4-Bis(benzyloxy)-5-brombenzaldehyd；3-Bromo-4,5-bis(phenylmethoxy)benzaldehyde
• CAS: 124662-50-6
• 化学式: C₂₁H₁₇BrO₃
• 分子量: 397.268
• InChiKey: BADXSCCLSFTJAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  5-bromo-3,4-dibenzyloxybenzaldehyde 在 正丁基锂 、 copper(I) bromide dimethylsulfide complex 、 sodium 、 对甲苯磺酸 作用下， 以 乙醚 、 仲丁醇 、 苯 为溶剂， 生成 3,4-二羟基-5-(3-甲基-2-丁烯-1-基)苯甲醛
  参考文献：
  名称：

  Application of benzyl protecting groups in the synthesis of prenylated aromatic compounds

  摘要：

  Benzyl ethers have proven to be useful protecting groups for synthesis of phenols bearing isoprenoid chains because the benzyl groups can tolerate the conditions of halogen-metal exchange used to introduce the side chains yet are cleaved in good yields upon treatment with sodium s-butanol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.187
• 作为产物：
  描述：

  5-溴-3, 4-二羟苯甲醛 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-3,4-dibenzyloxybenzaldehyde
  参考文献：
  名称：

  Application of benzyl protecting groups in the synthesis of prenylated aromatic compounds

  摘要：

  Benzyl ethers have proven to be useful protecting groups for synthesis of phenols bearing isoprenoid chains because the benzyl groups can tolerate the conditions of halogen-metal exchange used to introduce the side chains yet are cleaved in good yields upon treatment with sodium s-butanol. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.187

文献信息

• Total synthesis of silychristin, an antihepatotoxic flavonolignan.
  作者：Hitoshi TANAKA、Masaru HIROO、Kazuhiko ICHINO、Kazuo ITO

  DOI：10.1248/cpb.37.1441

  日期：——

  The total synthesis of silychristin, an antihepatotoxic flavonolignan, is described. The key intermediate, the transdihydrobenzofuran (15) was synthesized as follows. Treatment of the chalcone epoxide (9) with boron trifluoride etherate and subsequent reduction with sodium borohydride gave exclusively the erythro-1, 2-diaryl-1, 3-propanediol (10). Hydrogenolysis of 10 with hydrogen over a palladium catalyst followed by cyclization of the debenzylation product (13) with boron trifluoride etherate in acetic acid afforded 15 as a single product.

  描述了水飞蓟汀（一种抗肝毒性黄酮木脂素）的全合成。关键中间体反式二氢苯并呋喃 (15) 的合成如下。用乙醚三氟化硼处理查耳酮环氧化物(9)，随后用硼氢化钠还原，仅得到赤式-1,2-二芳基-1,3-丙二醇(10)。在钯催化剂上用氢气氢解10，然后用三氟化硼醚合物在乙酸中环化脱苄基产物(13)，得到单一产物15。
• Total synthesis of silychristin, an antihepatotoxic flavonolignan
  作者：Hitoshi Tanaka、Masaru Hiroo、Kazuhiko Ichino、Kazuo Ito

  DOI：10.1039/c39880000749

  日期：——

  The first total synthesis of silychristin is reported; the key intermediate [the dihydrobenzofuran (9)] was easily prepared in three steps from the readily available chalcone epoxide (6).

  据报道，首次合成了水飞蓟素。关键中间体[二氢苯并呋喃（9）]可以容易地从容易获得的查尔酮环氧化物（6）分三步制备。
• Synthesis of dihydroxycarboranyl phenylalanine for potential use in boron neutron capture therapy or melanoma
  作者：Jognandan K Prashar、Dobrochna Lama、Douglas E Moore

  DOI：10.1016/s0040-4039(00)61705-7

  日期：1993.10

  A dihydroxyphenylalanine derivative incorporating the 1,2-dicarba-closo- dodecaborane (12) cage has been synthesised from 3,4-dihydroxybenzaldehyde. The hydroxy groups were protected by benzylation, the carborane cage introduced via an acetylene substituent and the aminoacid function via diethylformamidomalonate.

  结合有二羟基苯衍生物的1,2- dicarba-闭合碳-十二硼烷（12），笼已经由3,4-二羟基苯甲醛合成。通过苄基化保护羟基，通过乙炔基取代基引入碳硼烷笼，并通过二乙基甲酰胺基丙二酸酯来保护氨基酸功能。
• Kametler, Laszlo; Keserue, Gyoergy M.; Nogradi, Mihaly, Liebigs Annalen der Chemie, 1992, # 12, p. 1239 - 1244
  作者：Kametler, Laszlo、Keserue, Gyoergy M.、Nogradi, Mihaly、Mezey-Vandor, Gabriella、Vermes, Borbala、Kajtar-Peredy, Maria

  DOI：——

  日期：——
• TANAKA, HITOSHI;HIROO, MASARU;ICHINO, KAZUHIKO;ITO, KAZUO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1441-1445
  作者：TANAKA, HITOSHI、HIROO, MASARU、ICHINO, KAZUHIKO、ITO, KAZUO

  DOI：——

  日期：——