2-(2-苯基-1H-咪唑并[1,2-a]苯并咪唑-1-基)乙醇 | 36289-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(2-苯基-1H-咪唑并[1,2-a]苯并咪唑-1-基)乙醇
• 英文名称: 2-(2-phenyl-1H-imidazo[1,2-a]benzimidazol-1-yl)ethanol
• 英文别名: 1-(2-hydroxyethyl)-2-phenylimidazo[1,2-a]benzimidazole；2-(2-phenyl-benzo[d]imidazo[1,2-a]imidazol-1-yl)-ethanol；2-(2-phenylimidazo[1,2-a]benzimidazol-3-yl)ethanol
• CAS: 36289-13-1
• 化学式: C₁₇H₁₅N₃O
• mdl: MFCD00964837
• 分子量: 277.326
• InChiKey: XXBXEYPJLVNJQC-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  488.9±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2-苯基-1H-咪唑并[1,2-a]苯并咪唑-1-基)乙醇 在 氢溴酸 作用下， 以 水 为溶剂， 生成 2-(2-bromoethylamino)-1-phenacylbenzimidazole hydrobromide
  参考文献：
  名称：

  Research in the field of imidazo[1,2-a]benzimidazole derivatives: XXVII. 1-acylmethyl-2-(ω-hydroxyalkylamino)-benzimidazoles and their transformation into derivatives of tricyclic systems

  摘要：

  1-Acylmethyl-2-(omega-hydroxyalkylamino)benzimidazoles were synthesized and their behavior under various conditions was investigated: at the thermolysis without solvent, at heating in DMF or in 2-aminoethanol, hydrohalic acids, and acetic anhydride, in the presence of chlorinating agents (SOCl(2), POCl(3)). Depending on the reaction conditions derivatives were obtained of 1H-imidazo[1,2-a]-benzimidazole, 9H-2,3-dihydroimidazo[1,2-a]benzimidazole, and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]-benzimidazole that were suitable synthons for the synthesis of functionally substituted derivatives of these tricyclic systems.

  DOI：

  10.1134/s1070428010020223
• 作为产物：
  描述：

  2-{2-[(2-羟基乙基)氨基]-1H-苯并咪唑-1-基}-1-苯乙酮 反应 1.5h， 以80%的产率得到2-(2-苯基-1H-咪唑并[1,2-a]苯并咪唑-1-基)乙醇
  参考文献：
  名称：

  Research in the field of imidazo[1,2-a]benzimidazole derivatives: XXVII. 1-acylmethyl-2-(ω-hydroxyalkylamino)-benzimidazoles and their transformation into derivatives of tricyclic systems

  摘要：

  1-Acylmethyl-2-(omega-hydroxyalkylamino)benzimidazoles were synthesized and their behavior under various conditions was investigated: at the thermolysis without solvent, at heating in DMF or in 2-aminoethanol, hydrohalic acids, and acetic anhydride, in the presence of chlorinating agents (SOCl(2), POCl(3)). Depending on the reaction conditions derivatives were obtained of 1H-imidazo[1,2-a]-benzimidazole, 9H-2,3-dihydroimidazo[1,2-a]benzimidazole, and 10H-2,3,4,10-tetrahydropyrimido[1,2-a]-benzimidazole that were suitable synthons for the synthesis of functionally substituted derivatives of these tricyclic systems.

  DOI：

  10.1134/s1070428010020223

文献信息

• Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer
  作者：Kim Spielmann、Ming Xiang、Leyah A. Schwartz、Michael J. Krische

  DOI：10.1021/jacs.9b08715

  日期：2019.9.11

  primary alcohols 2a-2z, 2a'-2c' engage in hydrogen auto-transfer-mediated carbonyl reductive coupling by way of (α-amino)allyliridium-aldehyde pairs to form vicinal amino alcohols 3a-3z, 3a'-3c' with high levels of regio-, anti-diastereo-, and enantioselectivity. Reaction progress kinetic analysis and isotopic labeling studies corroborate a catalytic cycle involving turnover-limiting alcohol dehydrogenation

  描述了第一个催化对映选择性羰基（α-氨基）烯丙基化。邻苯二甲酰亚胺-丙二烯 1 和伯醇 2a-2z, 2a'-2c' 通过（α-氨基）烯丙基铱-醛对参与氢自动转移介导的羰基还原偶联，形成邻氨基醇 3a-3z, 3a' -3c' 具有高水平的区域选择性、反非对映选择性和对映选择性。反应进程动力学分析和同位素标记研究证实了催化循环，包括限制周转的醇脱氢，然后是快速丙二烯加氢金属化。
• 1-Acylmethylbenzimidazole-2-sulfonic acids and their cyclization by N-nucleophiles
  作者：T. A. Kuz’menko、L. N. Divaeva、A. S. Morkovnik、V. A. Anisimova、G. S. Borodkin、V. V. Kuz’menko

  DOI：10.1134/s1070428014050169

  日期：2014.5

  New preparation method was developed for derivatives of 1,4-dihydro-1,2,4-triazino[4,3-a]-, 2-aryl-1(9)H-, and 1-R-imidazo[1,2-a]benzimidazole underlain by newly synthesized 1-acylmethylbenzimidazole-2-sulfonic acids. The latter react with 2-aminoethanol affording along with the previously described compounds of the 1-(2-hydroxyethyl)imidazobenzimidazole series also compounds of formerly unknown polycyclic system, 2,3,11,12-tetrahydro-1,3-oxazolo[2,3-a]imidazo[1,2-a]benzimidazole.