3-(1-羟基-2-硝基乙基)苯甲腈 | 550364-00-6

• 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: 3-(1-羟基-2-硝基乙基)苯甲腈
• 英文名称: 3-(1-hydroxy-2-nitroethyl)benzonitrile
• 英文别名: 1-(3-cyanophenyl)-2-nitroethanol
• CAS: 550364-00-6
• 化学式: C₉H₈N₂O₃
• 分子量: 192.174
• InChiKey: CJNMVCRENJTDJY-UHFFFAOYSA-N

物化性质

• 沸点：
  383.1±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1-羟基-2-硝基乙基)苯甲腈 在 镍 咪唑 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-3-{1-hydroxy-2-[3-(6-imidazol-yl-4-methyl-1H-benzimidazol-2-yl)-2-oxo-1,2-dihydro-pyridin-4-ylamino]-ethyl}-benzonitrile
  参考文献：
  名称：

  Novel 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase

  摘要：

  A novel class of 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase is described. This report discusses the SAR of 4-(2-hydroxy-2-phenylethylamino)-substituted pyridones with improved IGF-1R potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.041
• 作为产物：
  描述：

  硝基甲烷 、 3-氰基苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 3-(1-羟基-2-硝基乙基)苯甲腈
  参考文献：
  名称：

  氨基异冰片酚Schiff碱Cu2（SBAIB-d）2的铜配合物：直接催化不对称硝基吲哚（Henry）反应的高效催化剂

  摘要：

  为有效的直接催化不对称亨利反应，开发了一种新的氨基异冰片醇席夫碱双功能铜配合物Cu 2（SBAIB-d）2。一摩尔％的这种催化剂可产生高收率（高达99％ee）的预期亨利产物，并具有出色的对映选择性（高达98％ee）。本催化剂的实用性也扩展到了与硝基乙烷和1-硝基丙烷的亨利反应，从而以中等至高的收率（高达99％）提供了相应的产物，同时具有中等至高的对映体选择性的顺式（高达98％ee）和反（高达98％ee）非对映体。该催化体系的亮点是易于操作，耐空气和湿气，需要1摩尔％的易于合成的催化剂以及对多种底物都具有很高的对映选择性。

  DOI：

  10.1002/adsc.201200337

文献信息

• Cu ₆ S ₆ Clusters as a Building Block for the Stabilization of Coordination Polymers with NiAs, NaCl, and Related Structures: Synthesis, Structure, and Catalytic Studies
  作者：Ajay Kumar Jana、Srinivasan Natarajan

  DOI：10.1002/ejic.201701262

  日期：2018.2.14

  crystallography. The compounds consist of Cu6S6 octahedral clusters linked through the carboxylates to different zinc-oxo clusters. Thus, the compounds contain Cu-I- and Zn-II-based clusters, which are not commonly observed in coordination polymer structures. Compound I stabilizes in a NiAs-related structure, compounds II and IV in a NaCl-related structure, and compound III is a new type of network structure

  四种新型三维异金属配位聚合物 (CPs), Zn-3(Hen)(OH)}Cu-6(6-mna)(6)} (H2O)(6)] (I), Zn- 2(OH)(en)}Cu-6(6-mna)(6)}(0.5) (H2O)(2) EtO H ] (II), Zn-3(dap)(3)(H2O) }Cu-6(6-mna)(6)} (H2O)(4)] (III) 和 Zn-2(4,4-bpy)(0.5)(OH)(H2O)}Cu- 6(6-mna)(6)}(0.5) (H 2O)] (IV) (en = 乙二胺，6-H(2)mna = 6-巯基烟酸，dap = 1,2-二氨基丙烷，4,4 -bpy = 4,4-联吡啶），已经合成并通过单晶 X 射线晶体学确定了它们的结构。这些化合物由通过羧酸盐连接到不同锌氧簇的 Cu6S6 八面体簇组成。因此，这些化合物包含基于 Cu-I 和 Zn-II
• Highly efficient and large-scalable glucoamylase-catalyzed Henry reactions
  作者：Na Gao、Yan-Li Chen、Yan-Hong He、Zhi Guan

  DOI：10.1039/c3ra41287c

  日期：——

  Eco-friendly, highly efficient and large-scalable Henry reactions of aromatic aldehydes and nitroalkanes catalyzed by glucoamylase from Aspergillus niger (AnGA) are described. The reactions were carried out at 30 °C in the mixed solvents of ethanol and water, and the corresponding β-nitro alcohols were obtained in yields of up to 99%. Only 3 mg of enzyme was sufficient to catalyze the reaction of 1 mmol aldehydes. The natural activity and promiscuous activity of AnGA were compared under different conditions. Experiments demonstrated that the product of the Henry reaction could inhibit AnGA at 80 °C. This enzymatic Henry reaction showed a broad substrate scope, and could be facilely enlarged to gram scale. The possible mechanism was also discussed.

  本研究描述了黑曲霉（AnGA）的葡萄糖淀粉酶催化的芳香醛和硝基烷烃的环保、高效和大规模亨利反应。反应在乙醇和水混合溶剂中于 30 °C下进行，可获得相应的β-硝基醇，产率高达99%。仅 3 毫克酶就足以催化 1 毫摩尔醛的反应。比较了 AnGA 在不同条件下的天然活性和杂化活性。实验证明，亨利反应的产物在 80 °C下可抑制 AnGA。这种酶促亨利反应的底物范围很广，可以很容易地扩大到克级。此外，还讨论了可能的机理。
• Heteroaryl substituted triazole modulators of metabotropic glutamate receptor-5
  申请人：Cosford D.P. Nicholas

  公开号：US20050020585A1

  公开（公告）日：2005-01-27

  Triazole compounds substituted directly, or by a bridge, with a heteroaryl moiety containing N adjacent to the point of connection of the heteroaryl which are metabotropic glutamate receptor—subtype 5 (“mGluR5”) modulators useful in the treatment of psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, bipolar disorder and panic, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other diseases.

  直接或通过桥连基取代的三唑化合物，其杂环芳基团含有与杂环芳基连接点相邻的N，可作为代谢型谷氨酸受体亚型5（“mGluR5”）调节剂，用于治疗精神和情绪障碍，例如精神分裂症、焦虑症、抑郁症、双相障碍和惊恐症，以及用于治疗疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律紊乱、药物成瘾、药物滥用、药物戒断和其他疾病。
• Discovery of Novel Heteroarylazoles That Are Metabotropic Glutamate Subtype 5 Receptor Antagonists with Anxiolytic Activity
  作者：Jeffrey Roppe、Nicholas D. Smith、Dehua Huang、Lida Tehrani、Bowei Wang、Jeffrey Anderson、Jesse Brodkin、Janice Chung、Xiaohui Jiang、Christopher King、Benito Munoz、Mark A. Varney、Petpiboon Prasit、Nicholas D. P. Cosford

  DOI：10.1021/jm049828c

  日期：2004.9.1

  The highly potent, selective, and brain-penetrant metabotropic glutamate subtype 5 (mGlu5) receptor antagonists 3-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (47) and 3-fluoro-5-(5-pyridin-2-yl-2H-tetrazol-2-yl)benzonitrile (48) are reported. Compound 47 is active in the rat fear-potentiated startle (FPS) model of anxiety with ED50 = 5.4 mg/kg (po) when dosed acutely. In this model the anxiolytic effects of 47 rapidly tolerate on repeated dosing.
• An efficient synthesis of α-hydroxy phosphonates and 2-nitroalkanols using Ba(OH)2 as catalyst
  作者：Muthupandi Pandi、Prem Kumar Chanani、Sekar Govindasamy

  DOI：10.1016/j.apcata.2012.07.011

  日期：2012.10

  The alpha-hydroxy phosphonates have been synthesized using simple, inexpensive, and commonly available Ba(OH)(2)center dot 8H(2)O at room temperature and quantitative yields were obtained in just 15 min for most of the reactions. On applying the same reaction condition to aqueous mediated Henry reaction, 2-nitroalkanols were obtained in good to excellent yield within 15 min. (C) 2012 Elsevier B.V. All rights reserved.