α-cyano-β-hydroxycinnamonitrile | 5515-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-cyano-β-hydroxycinnamonitrile
• 英文别名: 2-(hydroxy(phenyl)methylene)malononitrile；α-Hydroxy-benzyliden-malonsaeure-dinitril；2-Cyan-3-hydroxy-3-phenyl-acrylonitril；Benzoylmalodinitrilenol；[Hydroxy(phenyl)methylene]malononitrile；2-[hydroxy(phenyl)methylidene]propanedinitrile
• CAS: 5515-36-6
• 化学式: C₁₀H₆N₂O
• 分子量: 170.17
• InChiKey: DBAYPSSCFJDLNA-UHFFFAOYSA-N

物化性质

• 沸点：
  295.0±40.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  α-cyano-β-hydroxycinnamonitrile 在 盐酸肼 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-氨基-5-苯基-1H-吡唑-4-甲腈
  参考文献：
  名称：

  Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

  摘要：

  A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 mu M. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.047
• 作为产物：
  描述：

  1,1-二氰基-2-甲氧基-2-(苯基)乙烯 在 potassium chloride 、 hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 α-cyano-β-hydroxycinnamonitrile
  参考文献：
  名称：

  解开 SNV 反应中的结构 - 反应性关系：甲氧基苯亚甲基丙二腈、2-（甲基硫代苯亚甲基）-1,3-茚二酮、2-（苄硫基苯亚甲基）-1,3-茚二酮和 β-甲硫基-α-硝基肉桂酸甲酯的反应动力学含水 DMSO 中的 OH 和硫醇盐离子

  摘要：

  标题反应的动力学在 50% DMSO-50% 水 (v/v) 中于 20 摄氏度进行测定；n-BuS-、HOCH2CH2S- 和 MeO2CCH2S- 用作硫醇盐离子。与硫醇盐离子的反应产生两个独立的动力学过程。第一个是指 RS- 与底物的快速、可逆连接，导致四面体中间体 (k1RS)，k(-1)RS，第二个是中间体转化为产物 (k2RS)。在大多数情况下，可以确定所有速率常数（k1RS、k(-1)RS 和 k2RS。结合先前研究的结果，详细讨论了活化取代基和离去基团对速率常数和平衡常数的影响与本征速率常数一样，与 OH- 的反应仅允许测定 k1OH 对底物的亲核攻击；

  DOI：

  10.1021/ja003536t

文献信息

• [EN] BRUTON'S TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE DE BRUTON
  申请人：PFIZER

  公开号：WO2014068527A1

  公开（公告）日：2014-05-08

  Disclosed herein are compounds that form covalent bonds with Bruton's tyrosine kinase (BTK). Methods for the preparation of the compounds are disclosed. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the BTK inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions. (Formula I)

  本文披露了一种与Bruton's酪氨酸激酶（BTK）形成共价键的化合物。公开了制备这些化合物的方法。还披露了包括这些化合物的药物组合物。公开了使用BTK抑制剂的方法，单独或与其他治疗剂联合治疗自身免疫疾病或症状、异源免疫疾病或症状、癌症，包括淋巴瘤，以及炎症性疾病或症状的方法。 (化学式I)
• Pyrrolopyrimidine thion derivatives
  申请人：Tsutsumi Takaharu

  公开号：US20050153992A1

  公开（公告）日：2005-07-14

  A compound having GSK-3 inhibiting function. A 1 and A 3 are a single bond, an aliphatic hydrocarbon group; A 2 and A 4 are a single bond, CO, COO, CONR, O, OCO, NR, NRCO, NRCOO, etc.; G 1 is a single bond, an aliphatic hydrocarbon, aromatic hydrocarbon, heterocyclic; G 2 is a hydrogen atom, an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, heterocyclic; A 5 is a single bond, NR; R 2 is H, halogen, an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocyclic; A 6 is a single bond, NR, CO, NRCO, NRCONR, CONR, COO, O, etc.; R 3 is H, halogen, nitro, saturated aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocyclic; and when A 6 is CR═CR or C≡C; R 3 may be a trimethylsilyl, formyl, acyl, carboxyl, alkoxylcarbonyl, carbamoyl, alkylcarbamoyl or cyano group; and R is H or an aliphatic hydrocarbon group.

  一种具有GSK-3抑制功能的化合物。A1和A3是单键，是脂肪烃基；A2和A4是单键，CO，COO，CONR，O，OCO，NR，NRCO，NRCOO等；G1是单键，是脂肪烃，芳香烃，杂环；G2是氢原子，脂肪烃，脂环烃，芳香烃，杂环；A5是单键，NR；R2是H，卤素，脂肪烃，脂环烃，芳香烃，杂环；A6是单键，NR，CO，NRCO，NRCONR，CONR，COO，O等；R3是H，卤素，硝基，饱和脂肪烃，脂环烃，芳香烃，杂环；当A6是CR═CR或C≡C时；R3可以是三甲基硅基，甲酰基，酰基，羧基，烷氧羰基，氨基甲酰，烷基氨基甲酰或氰基；R是H或脂肪烃基。
• Comprehensive Study of the Organic-Solvent-Free CDI-Mediated Acylation of Various Nucleophiles by Mechanochemistry
  作者：Thomas-Xavier Métro、Julien Bonnamour、Thomas Reidon、Anthony Duprez、Jordi Sarpoulet、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/chem.201501325

  日期：2015.9.1

  in the synthesis of natural products and biologically active compounds. Unfortunately, these reactions often require the use of large quantities of volatile and/or toxic solvents, either for the reaction, purification or isolation of the products. Herein we describe and discuss the possibility of completely eliminating the use of organic solvents for the synthesis, purification and isolation of products

  酰化反应在天然产物和生物活性化合物的合成中无处不在。不幸的是，这些反应通常需要使用大量的挥发性和/或有毒溶剂，用于反应，纯化或分离产物。本文中，我们描述和讨论了完全消除有机溶剂用于合成，纯化和分离由胺和其他亲核试剂酰化产生的产物的可能性。因此，利用N，N'羰基二咪唑（CDI）可在无溶剂机械搅拌下实现羧酸与各种亲核试剂之间的高效偶联，而水助研磨可实现纯产物的纯化和分离。分析和讨论了关键参数，例如产品的物理状态和水溶性，研磨材料，搅拌类型（振动或行星式搅拌）以及磨损造成的污染。此外，提出了原始的无溶剂有机溶剂条件，以克服这种方法的局限性。其中包括各种绿色指标的计算，突出了此策略对环境的影响特别小。
• Pyrrolopyrimidinone derivatives
  申请人：Tsutsumi Takaharu

  公开号：US20060160831A1

  公开（公告）日：2006-07-20

  A compound having GSK-3 inhibitory activity. A 1 and A 3 are a single bond, an aliphatic hydrocarbon group; A 2 and A 4 are a single bond, CO, COO, CONR, O, OCO, NR, NRCO, NRCOO, etc.; G 1 is a single bond, an aliphatic hydrocarbon, aromatic hydrocarbon, heterocyclic; G 2 is H, an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, heterocyclic; A 5 is a single bond, NR; R 2 is H, halogen, an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocyclic; A 6 is a single bond, NR, CO, NRCO, NRCONR, CONR, COO, O, etc.; R 3 is H, halogen, nitro, saturated aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocyclic; and R 3 may be a trimethylsilyl, formyl, acyl, carboxyl, alkoxylcarbonyl, carbamoyl, alkylcarbamoyl, or cyano group when A 6 is CR═CR or C≡C, wherein R is H or an lower aliphatic hydrocarbon group.

  具有GSK-3抑制活性的化合物。A1和A3是单键，脂肪烃基; A2和A4是单键，CO，COO，CONR，O，OCO，NR，NRCO，NRCOO等; G1是单键，脂肪烃，芳香烃，杂环; G2是H，脂肪烃，脂环烃，芳香烃，杂环; A5是单键，NR; R2是H，卤素，脂肪烃，脂环烃，芳香烃，杂环; A6是单键，NR，CO，NRCO，NRCONR，CONR，COO，O等; R3是H，卤素，硝基，饱和脂肪烃，脂环烃，芳香烃，杂环; 当A6为CR═CR或C≡C时，R3可以是三甲基硅烷基，甲酰基，酰基，羧基，烷氧基羰基，氨基甲酰基，烷基氨甲酰基或氰基。其中R是H或低级脂肪烃基。
• PHOTOCHROMIC AND ELECTROCHROMIC COMPOUNDS AND SYNTHESIS AND USE THEREOF
  申请人：Branda Neil R.

  公开号：US20100190868A1

  公开（公告）日：2010-07-29

  Novel photochromic and electrochromic hexadiene compounds are described. The compounds are reversibly convertible between ring-open and ring-closed isomeric forms as indicated in structures I(o) and I(c) below. (See formula in original abstract of application) The conversion between the different isomeric forms may be induced by light or electricity. In one embodiment the compounds may include a charge transfer moiety including electron donor and acceptor groups. The electron donor and acceptor are linearly conjugated in the ring-open form to enable electron transfer but are electrically insulated in the ring-closed form. Methods for synthesizing the compounds from photochemically and/or electrically inert precursors are also described. For example, the photoresponsive compounds may be synthesized by reacting diene precursors with dienophiles in a condensation reaction. The compounds may be utilized in reactivity-gated photochromic or electrochromic applications. In one embodiment of the invention, compounds of the invention may be used in a method to selectively release a releasable agent, such as a small molecule. According to this method, a photochemically inert precursor compound is reacted with the releasable agent to form a carrier compound comprising a switching moiety, the switching moiety being reversibly convertible between a thermally unstable form and a thermally stable form. The switching moiety may be selectively converted between the first and second forms to cause controlled release of the releasable agent from the carrier compound.

  本文描述了新型的光致变色和电致变色六烯基化合物。这些化合物可以在开环和闭环异构形式之间可逆转化，如下所示的结构I（o）和I（c）。 （请参见申请书原摘要中的公式）不同异构形式之间的转化可以通过光或电引发。在一种实施例中，这些化合物可以包括一个电荷转移基团，包括电子给体和受体基团。在开环形式中，电子给体和受体是线性共轭的，以实现电子转移，但在闭环形式中是电绝缘的。本文还描述了从光化学和/或电化学惰性前体合成这些化合物的方法。例如，可以通过将二烯前体与二烯酰亲合剂在缩合反应中反应来合成光响应化合物。这些化合物可以用于反应门控的光致变色或电致变色应用中。在本发明的一种实施例中，本发明的化合物可以用于选择性释放可释放剂（例如小分子）的方法。根据这种方法，将光化学惰性前体化合物与可释放剂反应以形成载体化合物，其中载体化合物包含可转换为热不稳定形式和热稳定形式的开关基团。可以选择性地在第一和第二形式之间转换开关基团，以从载体化合物中控制释放可释放剂。