3,4-二乙氧基苯甲腈 | 60758-87-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3,4-二乙氧基苯甲腈
• 中文别名: 3,4-二乙氧基苯腈
• 英文名称: 3,4-diethoxybenzonitrile
• 英文别名: 3,4-diethoxy-benzonitrile；3.4-Diaethoxy-benzoesaeure-nitril；3,4-Diaethoxy-benzonitril
• CAS: 60758-87-4
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD02256165
• 分子量: 191.23
• InChiKey: AQPTYFCFZUQSLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温下应保持干燥密封存储。

反应信息

• 作为反应物：
  描述：

  3,4-二乙氧基苯甲腈 在 盐酸 、 硫代乙酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74.5%的产率得到3,4-二乙氧基苯-1-甲硫代酰胺
  参考文献：
  名称：

  Novel Thiazole Derivatives as Inhibitors of Superoxide Production by Human Neutrophils: Synthesis and Structure-Activity Relationships

  摘要：

  Neutrophils have an important role in the self-defense systems of organisms through the production of superoxide. On the other hand, it has been proposed that abnormal amounts of superoxide produced by neutrophils are a serious factor in tissue injury. A series of novel thiazole derivatives was prepared and evaluated inhibitory effect on superoxide production by human neutrophils in vitro. Among these compounds, 6-[2-(3,4-diethoxyphenyl)thiazol-4-yl]-pyridine-2-carboxylic acid (OPC-6535) was selected as one of the most promising compounds. The synthesis and structure-activity relationships of these compounds are reported herein.

  DOI：

  10.1021/jm00002a017
• 作为产物：
  描述：

  乙基香兰素 在 sodium hydroxide 、 乙酸酐 作用下， 生成 3,4-二乙氧基苯甲腈
  参考文献：
  名称：

  MIXED BENZOINS. VIII. FURTHER DETERMINATIONS OF STRUCTURES. QUESTION OF ISOMERS

  摘要：

  DOI：

  10.1021/ja01347a043

文献信息

• An Efficient Method for the Preparation of Nitriles<i>via</i>the Dehydration of Aldoximes with Phthalic Anhydride
  作者：Eng-Chi Wang、Keng-Shiang Huang、Hsing-Ming Chen、Chung-Chin Wu、Gwo-Jiun Lin

  DOI：10.1002/jccs.200400093

  日期：2004.6

  highly efficient method for the conversion of aldoximes to nitriles was established. By fusing with phthalic anhydride, aldoximes were efficiently and smoothly converted into nitriles, in high yields (over 85%) and in a short time (within 5 minutes). The mixture of phthalic anhydride, a cyclic anhydride, and aldoximes in fusing state set up an ideal transition state for a selective [3.3]-sigmatropic

  建立了一种新的高效醛肟转化为腈的方法。通过与邻苯二甲酸酐的融合，醛肟以高产率（超过 85%）和在短时间内（5 分钟内）高效且顺利地转化为腈类。邻苯二甲酸酐、环状酸酐和融合态醛肟的混合物为酰化醛肟选择性[3.3]-σ迁移重排为腈建立了理想的过渡态。
• Thiazole derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05639770A1

  公开（公告）日：1997-06-17

  A thiazole derivative of the general formula: ##STR1## The thiazole derivatives have an excellent inhibitory activity for superoxide radical.

  一种通式为##STR1##的噻唑衍生物。这些噻唑衍生物对超氧自由基具有出色的抑制活性。
• Agent for inhibition of cytokine production and agent for inhibition of cell adhesion
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US06291487B1

  公开（公告）日：2001-09-18

  The present invention provides an agent for inhibiting cytokine production or cell adhesion, comprising at least one compound selected from the group consisting of thiazole derivatives represented by the following general formula: [wherein R1 is a phenyl group which may have a lower alkoxy group(s) as a substituent(s) on the phenyl ring, and R2 is a group represented by the following general formula: [wherein R3's, which may be the same or different, are each a carboxyl group, a lower alkoxy group or the like) or the like] and salts thereof.

  本发明提供了一种用于抑制细胞因子产生或细胞粘附的药剂，包括至少一种选择自以下一般式所代表的噻唑衍生物组合的化合物： [其中R1是苯基，苯环上可能有一个或多个较低的烷氧基作为取代基，R2是由以下一般式所代表的基团： [其中R3可能相同也可能不同，每个都是羧基、较低的烷氧基或类似物）或其盐。
• A new one pot method for the conversion of aldehydes into nitriles using hydroxyamine and phthalic anhydride
  作者：Eng-Chi Wang、Gow-Juin Lin

  DOI：10.1016/s0040-4039(98)00654-6

  日期：1998.6

  The aryl and alkyl aldehydes were readily converted to give the corresponding nitriles in good yields using hydroxyamine and phthalic anhydride as reagents in one pot.

  在一锅中使用羟胺和邻苯二甲酸酐作为试剂，很容易将芳基和烷基醛转化为高产率的相应腈。
• Aminoimidazoles as Potent and Selective Human β-Secretase (BACE1) Inhibitors
  作者：Michael S. Malamas、Jim Erdei、Iwan Gunawan、Keith Barnes、Matthew Johnson、Yu Hui、Jim Turner、Yun Hu、Erik Wagner、Kristi Fan、Andrea Olland、Jonathan Bard、Albert J. Robichaud

  DOI：10.1021/jm9006752

  日期：2009.10.22

  of small molecule aminoimidazoles as potent and selective human β-secretase inhibitors is reported. These analogues demonstrate low nannomolar potency for BACE1 in a FRET assay, exhibit comparable activity in a cell-based (ELISA) assay, and show >100× selectivity for the other structurally related aspartyl proteases BACE2, cathepsin D, renin, and pepsin. Our design strategy was supported by molecular

  报道了鉴定出小分子氨基咪唑作为有效的和选择性的人β-分泌酶抑制剂。这些类似物在FRET分析中显示出对BACE1较低的纳米摩尔效能，在基于细胞的（ELISA）分析中显示出可比的活性，并且对其他结构相关的天冬氨酰蛋白酶BACE2，组织蛋白酶D，肾素和胃蛋白酶显示出> 100倍的选择性。我们的设计策略得到了基于BACE1活性位点中HTS-hit 3共晶体结构的分子建模研究的支持。这些策略使我们能够整合3上的吡啶和嘧啶基团，这些基团延伸到BACE1结合口袋的S3区域深处，并增强了配体的效能。化合物（R）-37的IC 50与相关的天冬氨酰蛋白酶相比，BACE1的最大分子量为20 nM，细胞活性为90 nM，选择性大于100倍。在Tg2576小鼠模型中，在6小时的时间点，急性口服给予（R）-37的剂量为30 mg / kg导致血浆Aβ40显着降低71％（p <0.001）。