(1-烯丙基-1H-苯并咪唑-2-基)甲醇 | 300706-95-0

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (1-烯丙基-1H-苯并咪唑-2-基)甲醇
• 英文名称: (1-allyl-1H-benzo[d]imidazol-2-yl)methanol
• 英文别名: N-allyl-1H-benzimidazole-2-methanol；(1-allyl-1H-benzoimidazol-2-yl)-methanol；(1-prop-2-enylbenzimidazol-2-yl)methanol
• CAS: 300706-95-0
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD00964478
• 分子量: 188.229
• InChiKey: WCFBNPLGHKARRT-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  367.2±35.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (1-烯丙基-1H-苯并咪唑-2-基)甲醇 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以0.128 g的产率得到(9ci)-1-(2-丙烯基)-1H-苯并咪唑-2-羧醛
  参考文献：
  名称：

  N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles

  摘要：

  报道了N-杂环卡宾催化的N-烯基咪唑-2-甲醛和N-烯基苯并咪唑-2-甲醛的分子内羟酰化反应。这些对外部选择性的羟酰化反应使得未活化的烯烃能够以良好至优秀的产率合成各种基础的、多环的氮杂环化合物。

  DOI：

  10.1039/c6ob01956k
• 作为产物：
  描述：

  3-[2-(Hydroxymethyl)benzimidazol-1-yl]propanenitrile 在 碳酸氢钠 作用下， 生成 (1-烯丙基-1H-苯并咪唑-2-基)甲醇
  参考文献：
  名称：

  不饱和唑类的研究。13. 1-烷基苯并咪唑的合成及一些反应

  摘要：

  DOI：

  10.1007/bf01164866

文献信息

• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：——

  公开号：US20030220341A1

  公开（公告）日：2003-11-27

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  这项发明涉及由一个核心氮原子环绕着三个侧链基团的杂环化合物，其中三个侧链基团中的两个最好是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可选地含有额外的环。这些化合物与趋化因子受体结合，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。
• Sustainable Synthesis of 2‐Hydroxymethylbenzimidazoles using D‐Fructose as a C ₂ Synthon
  作者：Dineshkumar Raja、Abigail Philips、Devikala Sundaramurthy、Gopal Chandru Senadi

  DOI：10.1002/asia.202100972

  日期：2021.11.15

  carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine.

  D-果糖是一种生物质衍生的碳水化合物，在通过与 1,2-苯二胺偶联制备合成有用的 2-羟甲基苯并咪唑衍生物时，已将其鉴定为环境无害的 C 2合成子。该方法的关键特征包括无金属条件、时间短、官能团耐受性好、克级可行性和苯并咪唑稠合 1,4-恶嗪的合成。
• Synthesis of Pyrrolo- and Pyrido-[1,2-<i>a</i>]benzimidazolequinone Anti-tumor Agents Containing a Fused Cyclopropane Ring
  作者：Fawaz Aldabbagh、John O’Shaughnessy

  DOI：10.1055/s-2005-861832

  日期：——

  A cyclopropane ring has been fused onto tetrahydropyrrolo- and tetrahydropyrido-[1,2-a]-benzimidazoles and -benzimidazolequinones via the cycloaddition of diazomethines generated from the thermolysis of N-(allyl and but-3-enyl)benzimidazole-2-Eschenmoser hydrazones (aziridinyl imines). At lower temperatures, the 1,3-dipolar [3 + 2] cycloadduct was obtained for only the N-allylbenzimidazole-2-Eschenmoser

  通过 N-(烯丙基和丁-3-烯基)苯并咪唑-2-Eschenmoser 热解产生的重氮亚甲基环加成，环丙烷环已稠合到四氢吡咯并-和四氢吡啶并-[1,2-a]-苯并咪唑和苯并咪唑醌上腙（氮丙啶亚胺）。在较低温度下，仅 N-烯丙基苯并咪唑-2-Eschenmoser 腙得到 1,3-偶极 [3 + 2] 环加合物。
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS WITH ENHANCED EFFICACY
  申请人：BRIDGER Gary

  公开号：US20080167341A1

  公开（公告）日：2008-07-10

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  该发明涉及由一个核心氮原子和三个侧链基团组成的杂环化合物，其中三个侧链基团中有两个是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可以含有额外的环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护效果。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。