2-溴-3-(羟甲基)苯甲醛 | 1255794-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-3-(羟甲基)苯甲醛
• 英文名称: 2-bromo-3-hydroxymethylbenzaldehyde
• 英文别名: 2-Bromo-3-(hydroxymethyl)benzaldehyde；2-bromo-3-(hydroxymethyl)benzaldehyde
• CAS: 1255794-73-0
• 化学式: C₈H₇BrO₂
• 分子量: 215.046
• InChiKey: RAICACCJOSWWSB-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  331.8±32.0 °C(Predicted)
• 密度：
  1.640±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-溴-3-(羟甲基)苯甲醛 在 盐酸 、 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 盐酸羟胺 、 sodium acetate 、 三溴化硼 、 potassium carbonate 、 二异丙胺 、 对甲苯磺酰氯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 82.5h， 生成 alangiumkaloid A
  参考文献：
  名称：

  两种8-氧代小ber碱生物碱的总合成：lang兰碱A和B

  摘要：

  我们通过构造异喹啉酮骨架（由2-炔基苯甲醛肟热环化生成异喹啉N-氧化物，然后再形成Reissert-Henze型）形成异喹啉酮骨架，描述了首个总合成Alangiumkaloids A（1）和B（2）的细节。反应。

  DOI：

  10.1002/ejoc.201701557
• 作为产物：
  描述：

  2,6-二甲基溴苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 calcium carbonate 作用下， 以 四氯化碳 、 1,4-二氧六环 为溶剂， 反应 48.0h， 以60%的产率得到2-溴-3-(羟甲基)苯甲醛
  参考文献：
  名称：

  Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel

  摘要：

  Novel paclitaxel-mimicking alkaloids were designed and synthesized based on a bioactive conformation of paclitaxel, that is, REDOR-Taxol. The alkaloid 2 bearing a 5-7-6 tricyclic scaffold mimics REDOR-Taxol best among the compounds designed and was found to be the most potent compound against several drug-sensitive and drug-resistant human cancer cell lines. MD simulation study on the paclitaxel mimics 1 and 2 as well as REDOR-Taxol bound to the 1JFF tubulin structure was quite informative to evaluate the level of mimicking. The MD simulation study clearly distinguishes the 5-6-6 and 5-7-6 tricyclic scaffolds, and also shows substantial difference in the conformational stability of the tubulin-bound structures between 2 and REDOR-Taxol. The latter may account for the large difference in potency, and provides critical information for possible improvement in the future design of paclitaxel mimics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.069

文献信息

• Benzoxaborole antimalarial agents. Part 2: Discovery of fluoro-substituted 7-(2-carboxyethyl)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles
  作者：Yong-Kang Zhang、Jacob J. Plattner、Yvonne R. Freund、Eric E. Easom、Yasheen Zhou、Long Ye、Huchen Zhou、David Waterson、Francisco-Javier Gamo、Laura M. Sanz、Min Ge、Zhiya Li、Lingchao Li、Hailong Wang、Han Cui

  DOI：10.1016/j.bmcl.2011.12.096

  日期：2012.2

  A series of new boron-containing benzoxaborole compounds was designed and synthesized for a continuing structure–activity relationship (SAR) investigation to assess the antimalarial activity changes derived from side-chain structural variation, substituent modification on the benzene ring and removal of boron from five-membered oxaborole ring. This SAR study demonstrated that boron is required for

  设计并合成了一系列新的含硼苯并氧杂硼烷化合物，用于持续的结构-活性关系（SAR）研究，以评估由侧链结构变化，苯环上的取代基修饰和从五个基团中除去硼引起的抗疟活性变化。元氧杂硼酸酯环。此SAR研究表明，硼是必需的抗疟活性，并发现三个氟取代的7-（2-羧基乙基）-1,3-二氢-1-羟基-2,1- benzoxaboroles（9，14和20）对恶性疟原虫具有出色的效价（IC 50 0.026–0.209μM）。
• Mechanistic Studies on the Bismuth‐Catalyzed Transfer Hydrogenation of Azoarenes
  作者：Hye Won Moon、Feng Wang、Kalishankar Bhattacharyya、Oriol Planas、Markus Leutzsch、Nils Nöthling、Alexander A. Auer、Josep Cornella

  DOI：10.1002/anie.202313578

  日期：2023.12.4

  study of the bismuth-catalyzed transfer hydrogenation of azoarenes. With the protocol using p-trifluoromethylphenol and pinacolborane, we identified the role of protic and hydridic hydrogens through kinetic analysis and reactivity studies. The possibility of Bi-ligand cooperativity was assessed through isotope labeling experiments. This work validates the notion of Bi(I)/Bi(III) redox cycling.

  我们报告了铋催化偶氮芳烃转移氢化的实验和计算相结合的研究。通过使用对三氟甲基苯酚和频哪醇硼烷的方案，我们通过动力学分析和反应性研究确定了质子氢和氢氢的作用。通过同位素标记实验评估双配体协同性的可能性。这项工作验证了 Bi(I)/Bi(III) 氧化还原循环的概念。
• Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel
  作者：Liang Sun、Jean M. Veith、Paula Pera、Ralph J. Bernacki、Iwao Ojima

  DOI：10.1016/j.bmc.2010.07.069

  日期：2010.10

  Novel paclitaxel-mimicking alkaloids were designed and synthesized based on a bioactive conformation of paclitaxel, that is, REDOR-Taxol. The alkaloid 2 bearing a 5-7-6 tricyclic scaffold mimics REDOR-Taxol best among the compounds designed and was found to be the most potent compound against several drug-sensitive and drug-resistant human cancer cell lines. MD simulation study on the paclitaxel mimics 1 and 2 as well as REDOR-Taxol bound to the 1JFF tubulin structure was quite informative to evaluate the level of mimicking. The MD simulation study clearly distinguishes the 5-6-6 and 5-7-6 tricyclic scaffolds, and also shows substantial difference in the conformational stability of the tubulin-bound structures between 2 and REDOR-Taxol. The latter may account for the large difference in potency, and provides critical information for possible improvement in the future design of paclitaxel mimics. (C) 2010 Elsevier Ltd. All rights reserved.
• Total Synthesis of Two 8-Oxoprotoberberine Alkaloids: Alangiumkaloids A and B
  作者：Takashi Nishiyama、Miharu Hironaka、Mizuki Taketomi、Eri Taguchi、Rika Kotouge、Yoshiyuki Shigemori、Noriyuki Hatae、Minoru Ishikura、Tominari Choshi

  DOI：10.1002/ejoc.201701557

  日期：2018.2.7

  We describe the details of the first total synthesis of alangiumkaloids A (1) and B (2) through construction of an isoquinolinone framework formed by thermal cyclization of 2‐alkynylbenzaldehyde oxime to produce isoquinoline N‐oxide, followed by a Reissert–Henze‐type reaction.

  我们通过构造异喹啉酮骨架（由2-炔基苯甲醛肟热环化生成异喹啉N-氧化物，然后再形成Reissert-Henze型）形成异喹啉酮骨架，描述了首个总合成Alangiumkaloids A（1）和B（2）的细节。反应。