4-(2-benzyloxy-3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(2-benzyloxy-3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one
• 英文别名: (Z)-4-(2-(benzyloxy)-3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one；(4Z)-4-[(3,5-dibromo-4-methoxy-2-phenylmethoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one
• 化学式: C₁₉H₁₅Br₂NO₄
• 分子量: 481.14
• InChiKey: LTFZRRXAPSVWKZ-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-benzyloxy-3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one 在 10% palladium on active carbon 氢氧化钾 、 盐酸羟胺 、 氢气 作用下， 反应 6.0h， 生成 N,N'-bis<3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropionyl>-1,4-butanediamine
  参考文献：
  名称：

  (±)-Aerothionin、(±)-Homoaerothionin 和 (±)-Aerophobin-1 的全合成

  摘要：

  (±)-Aerothionin、(±)-homoaerothionin 和 (±)-aerophobin-1 已成功合成，使用三氟乙酸铊 (III) 对丙酮酸甲酯肟衍生物的酚氧化作为关键步骤。通过将 1H NMR 光谱与相关化合物的光谱进行比较，还确定了 Aerophobin-2 的立体结构。

  DOI：

  10.1246/bcsj.58.3453
• 作为产物：
  描述：

  2-Benzyloxy-3,5-dibrom-4-methoxybenzaldehyd 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 反应 6.0h， 生成 4-(2-benzyloxy-3,5-dibromo-4-methoxybenzylidene)-2-methyloxazol-5(4H)-one
  参考文献：
  名称：

  Total syntheses of subereamollines A and B

  摘要：

  首次报道了(+)-和(−)-subereamollines A和B的完整合成。这些天然产物的对映体形式通过相应外消旋体的制备性手性高效液相色谱分离获得。

  DOI：

  10.1039/c0ob00636j

文献信息

• Oxidative cyclisation of o-phenolic oxime-acid derivatives using phenyliodonium diacetate: Synthesis of spiroisoxazoline derivatives
  作者：Masatoshi Murakata、Kohei Yamada、Osamu Hoshino

  DOI：10.1016/0040-4020(96)00921-0

  日期：1996.11

  An efficient formation of spiroisoxazoline ring system by intramolecular oxidative cyclisation of o-phenolic oxime-esters and oxime-amides using phenyliodonium diacetate (PIDA) is described. The intramolecular oxidative cyclisation of various o-phenolic oxime-acid derivatives in acetonitrile at 0 °C proceeded smoothly to afford spiroisoxazolines in good yields. Synthesis of o-phenolic oxime-esters

  描述了通过使用二乙酸苯基碘鎓（PIDA）对邻-酚类肟酯和肟酰胺进行分子内氧化环化来有效形成螺异恶唑啉环系统。各种邻苯酚肟酸衍生物在乙腈中的分子内氧化环化在0°C进行得很顺利，以高收率得到螺异恶唑啉。还描述了邻苯酚肟酯和肟酰胺的合成。
• Synthesis and Biological Evaluation of Purealin and Analogues as Cytoplasmic Dynein Heavy Chain Inhibitors
  作者：Guangyu Zhu、Fanglong Yang、Raghavan Balachandran、Peter Höök、Richard B. Vallee、Dennis P. Curran、Billy W. Day

  DOI：10.1021/jm051030l

  日期：2006.3.1

  Cytoplasmic dynein plays important roles in membrane transport, mitosis, and other cellular processes. A few small-molecule inhibitors of cytoplasmic dynein have been identified. We report here the first synthesis of purealin, a natural product isolated from the sea sponge Psammaplysilla purea, which is known to inhibit axonemal dynein. Also described are the first syntheses, by modular amide coupling reactions, of the natural product purealidin A (a component of purealin) and a small library of analogues. The library was examined for inhibition of cytoplasmic dynein heavy chain and cell growth. The compounds showed effective antiproliferative activity against a mouse leukemia cell line but selective activities against human carcinoma cell lines. Purealin and some of the analogues inhibited the microtubule-stimulated ATPase activity of recombinant cytoplasmic dynein heavy chain motor domain. The inhibitory effect of purealin was concentration dependent and uncompetitive, supporting the hypothesis that it does not compete with the binding of ATP.
• Total syntheses of subereamollines A and B
  作者：James W. Shearman、Rebecca M. Myers、James D. Brenton、Steven V. Ley

  DOI：10.1039/c0ob00636j

  日期：——

  The first total syntheses of (+)- and (−)-subereamollines A and B are reported. The enantiomeric forms of the natural products were obtained by preparative chiral HPLC separation of the corresponding racemates.

  首次报道了(+)-和(−)-subereamollines A和B的完整合成。这些天然产物的对映体形式通过相应外消旋体的制备性手性高效液相色谱分离获得。
• Total Syntheses of (±)-Aerothionin, (±)-Homoaerothionin, and (±)-Aerophobin-1
  作者：Shigeru Nishiyama、Shosuke Yamamura

  DOI：10.1246/bcsj.58.3453

  日期：1985.12

  (±)-aerophobin-1 have been successfully synthesized using phenolic oxidation of the methyl pyruvate oxime derivative with thallium(III) trifluoroacetate as a key step. The stereostructure of aerophobin-2 has been also established by comparison of the 1H NMR spectrum with those of related compounds.

  (±)-Aerothionin、(±)-homoaerothionin 和 (±)-aerophobin-1 已成功合成，使用三氟乙酸铊 (III) 对丙酮酸甲酯肟衍生物的酚氧化作为关键步骤。通过将 1H NMR 光谱与相关化合物的光谱进行比较，还确定了 Aerophobin-2 的立体结构。