methyl 2-hydroxyimino-3-(2-hydroxy-3,5-dibromo-4-methoxyphenyl)propionate | 87580-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 2-hydroxyimino-3-(2-hydroxy-3,5-dibromo-4-methoxyphenyl)propionate
• 英文别名: methyl 3-(2-hydroxy-3,5-dibromo-4-methoxyphenyl)-2-hydroxyiminopropanoate；methyl 2-hydroxyimino-3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)propionate；Methyl 3-(3,5-dibromo-2-hydroxy-4-methoxyphenyl)-2-hydroxyiminopropanoate
• CAS: 87580-07-2
• 化学式: C₁₁H₁₁Br₂NO₅
• 分子量: 397.02
• InChiKey: OAVDDIVCPFDIAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxyimino-3-(2-hydroxy-3,5-dibromo-4-methoxyphenyl)propionate 在 zinc(II) tetrahydroborate 、 thallium(III) trifluoroacetate 作用下， 以 乙醚 、 二氯甲烷 、 三氟乙酸 为溶剂， 反应 4.12h， 生成 aerothionin
  参考文献：
  名称：

  （±）-aeroothionin和（±）-homoaerothionin的总合成

  摘要：

  海绵状Aplysina aerophoba，A。fistularis和Verongia thiona的新型代谢产物aerothionin和homoaerothionin均以外消旋形式合成。

  DOI：

  10.1016/s0040-4039(00)86267-x
• 作为产物：
  描述：

  methyl 2-benzyloxyimino-3-(2'-benzyloxy-3,5-dibromo-4-methoxyphenyl)propionate 在 钯 氢气 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 48.0h， 以67%的产率得到methyl 2-hydroxyimino-3-(2-hydroxy-3,5-dibromo-4-methoxyphenyl)propionate
  参考文献：
  名称：

  使用二乙酸苯基碘鎓的邻苯酚肟酸衍生物的氧化环化：螺异恶唑啉衍生物的合成

  摘要：

  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。

  DOI：

  10.1016/0040-4020(96)00921-0

文献信息

• Synthesis and assignment of the absolute stereochemistry of (+)-hemifistularin 3
  作者：Hironori Kubo、Kaori Matsui、Tsuyoshi Saitoh、Shigeru Nishiyama

  DOI：10.1016/j.tet.2014.07.049

  日期：2014.9

  the marine natural product (+)-hemifistularin 3 in enantiomerically pure form was accomplished by using the amide forming reaction of (+)-spiroisoxazoline ester with the (+)-octopamine derivative. The stereodivergent strategy employed in this effort enabled the assignment of the absolute configurations at the three stereogenic centers in (+)-hemifistularin 3.

  对映体纯形式的海洋天然产物（+）-hemististularin 3的第一个全合成是通过使用（+）-螺杂恶唑啉酯与（+）-章鱼胺衍生物的酰胺形成反应完成的。在这项工作中采用的立体发散策略使得能够在（+）-hemifistularin 3的三个立体发生中心分配绝对构型。
• Total Synthesis, Structural Revision, and Biological Evaluation of Calafianin, a Marine Spiroisoxazoline from the Sponge,<i>Aplysina gerardogreeni</i>
  作者：Takahisa Ogamino、Rika Obata、Hiroshi Tomoda、Shigeru Nishiyama

  DOI：10.1246/bcsj.79.134

  日期：2006.1

  The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol derivative 7, followed by Zn[BH4]2 reduction. Comparison of the spectroscopic data of the synthetic (±)-1 and (±)-13 resulted in structural revision of the natural calafianin to 13, possessing the trans-relationship between an epoxide and an oxygen of the isoxazoline. In addition, a significant difference of antimicrobial activity between 1 and 13 is discussed.

  报道的自然卡拉法宁（1）及其异构体在环氧区域13通过顺式和反式螺异噁唑啉化合物成功合成，这些化合物是通过对羟亚氨基苯酚衍生物7的电化学氧化产物，再经过Zn[BH4]2还原得到的。合成的（±）-1和（±）-13的光谱数据比较导致了对自然卡拉法宁结构的修订，确认其为13，具有环氧和异噁唑啉氧之间的反式关系。此外，还讨论了1和13之间抗菌活性显著差异。
• 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。
• 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.
• Ogamino, Takahisa; Ishikawa, Yuichi; Nishiyama, Shigeru, Heterocycles, 2003, vol. 61, p. 73 - 78
  作者：Ogamino, Takahisa、Ishikawa, Yuichi、Nishiyama, Shigeru

  DOI：——

  日期：——