(E)-3-(3-hydroxyphenyl)acrylonitrile | 26706-43-4

• 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: (E)-3-(3-hydroxyphenyl)acrylonitrile
• 英文别名: (E)-3-(3-hydroxyphenyl)prop-2-enenitrile
• CAS: 26706-43-4
• 化学式: C₉H₇NO
• 分子量: 145.161
• InChiKey: CZUDNLGWUDZMIN-DUXPYHPUSA-N

物化性质

• 沸点：
  340.2±25.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 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：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-hydroxyphenyl)acrylonitrile 在 铁粉 、 potassium carbonate 、 氯化铵 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 2-[3-[(E)-2-cyanovinyl]phenoxy]-4-[(4-methoxypyrimidin-2-yl)amino]benzonitrile
  参考文献：
  名称：

  Efficient Discovery of Potent Anti-HIV Agents Targeting the Tyr181Cys Variant of HIV Reverse Transcriptase

  摘要：

  Non-nucleoside reverse transcriptase inhibitors (NNRTIs) that interfere with the replication of human immunodeficiency virus (HIV) are being pursued with guidance from molecular modeling including free-energy perturbation (FEP) calculations for protein inhibitor binding affinities. The previously reported pyrimidinylphenylamine 1 and its chloro analogue 2 are potent anti-HIV agents; they inhibit replication of wild-type HIV-1 in infected human T-cells with EC50 values of 2 and 10 nM, respectively. However, they show no activity against viral strains containing the Tyr181Cys (Y181C) mutation in HIV-RT. Modeling indicates that the problem is likely associated with extensive interaction between the dimethylallyloxy substituent and Tyr181. As an alternative, a phenoxy group is computed to be oriented in a manner diminishing the contact with Tyr181. However, this replacement leads to a roughly 1000-fold loss of activity for 3 (2.5 mu M). The present report details the efficient, computationally driven evolution of 3 to novel NNRTIs with sub-10 nM potency toward both wild-type HIV-1 and Y181C-containing variants. The critical contributors were FEP substituent scans for the phenoxy and pyrimidine rings and recognition of potential benefits of addition of a cyanovinyl group to the phenoxy ring.

  DOI：

  10.1021/ja2058583
• 作为产物：
  描述：

  C₁₃H₈ClIO₂ 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (E)-3-(3-hydroxyphenyl)acrylonitrile
  参考文献：
  名称：

  在室温下将苯甲酸简单实用地转化为酚类

  摘要：

  酚类是重要的有机分子，因为它们在许多领域都有广泛的应用。本文报道了一种在室温下通过简单的有机试剂从苯甲酸制备酚类的有效实用方法。这种方法与各种官能团和杂环兼容，并且可以轻松放大。为了证明其合成效用，生物活性分子和不对称六芳基苯已通过利用这种转变作为战略步骤来制备。机理研究表明，关键的迁移步骤涉及游离碳正离子而不是自由基中间体。考虑到苯甲酸的丰富性和酚类的实用性，预计该方法将在有机合成中得到广泛的应用。

  DOI：

  10.1021/jacs.2c07529

文献信息

• [EN] PROCESS FOR HYDROCYANATION OF TERMINAL ALKYNES<br/>[FR] PROCÉDÉ D'HYDROCYANATION D'ALCYNES TERMINAUX
  申请人：STUDIENGESELLSCHAFT KOHLE MBH

  公开号：WO2018210631A1

  公开（公告）日：2018-11-22

  The present invention refers to a process for a Rh-catalyzed Anti-Markovnikov hydrocyanation of terminal alkynes which process discloses, for the first time, the highly stereo- and regio-selective hydrocyanation of terminal alkynes to furnish E- configured alkenyl nitriles and the catalyst used in the present process.

  本发明涉及一种Rh催化的末端炔烃反Markovnikov加氢过程，该过程首次披露了末端炔烃的高立体和区域选择性加氢，以生成E-构型的烯基腈和本过程中使用的催化剂。
• Rh-Catalyzed Anti-Markovnikov Hydrocyanation of Terminal Alkynes
  作者：Fei Ye、Junting Chen、Tobias Ritter

  DOI：10.1021/jacs.7b03749

  日期：2017.5.31

  We report the first highly stereo- and regioselective hydrocyanation of terminal alkynes to furnish E-configured alkenyl nitriles. Acrylonitriles can be accessed on gram scale with broad substrate scope and functional group tolerance. The hydrocyanation reaction employs acetone cyanohydrin as a practical alternative to HCN gas.

  我们报告了第一个高度立体和区域选择性的末端炔烃氢氰化反应，以提供 E 构型的烯基腈。丙烯腈可以在克级获得，具有广泛的底物范围和官能团耐受性。氢氰化反应使用丙酮氰醇作为 HCN 气体的实用替代品。
• Light-induced and related reactions of quinones. Part VI. Reactions of some p-quinones carrying formyl groups
  作者：J. Malcolm Bruce、David Creed

  DOI：10.1039/j39700000649

  日期：——

  ) propionaldehyde are described. Irradiation of solutions of these quinones in benzene with visible light leads to the isolation of 2,5-dihydroxybenzoic acid from formyl-1,4-benzoquinone, and to the formation of 5-hydroxycoumaran-2-one and 3,4-dihydro-6-hydroxycoumarin from the next two quinones, respectively; the last two quinones in the series lose the elements of formaldehyde, and give 5-hydrox

  甲酰基-1,4-苯醌，1,4-苯醌基乙醛，3-（1,4-苯醌基）丙醛，2-（1,4-苯醌基）-2-甲基丙醛和2-甲基-2-（1）的制备描述了（4-萘醌-2-基）丙醛。用可见光照射这些苯醌在苯中的溶液导致将2，5-二羟基苯甲酸从甲酰基-1，4-苯醌中分离出来，并形成5-羟基香豆素-2-酮和3,4-二氢-接下来的两个醌中的6-羟基香豆素；该系列中的最后两个醌失去甲醛元素，分别生成5-羟基-3-甲基苯并呋喃和5-羟基-3-甲基萘-[1,2- b ]呋喃。没有任何辐射进行得很干净。
• Synthesis and structure-activity study of protease inhibitors. III. Amidinophenols and their benzoil esters.
  作者：TAKASHI YAEGASHI、SHIGEKI NUNOMURA、TOSHIYUKI OKUTOME、TOYOO NAKAYAMA、MASATERU KURUMI、YOJIRO SAKURAI、TAKUO AOYAMA、SETSURO FUJII

  DOI：10.1248/cpb.32.4466

  日期：——

  Various amidinophenol derivatives (27-47) and their benzoates (4-26) were synthesized and evaluated for inhibitory activities against trypsin, plasmin, kallikrein, thrombin, Clr and Cls as well as in vitro complement-mediated hemolysis. 4-(β-Amidinoethenyl) phenyl 4-guanidinobenzoate (15) and 4-amidino-2-benzoylphenyl 4-guanidinobenzoate (26) were found to have potent inhibitory activities with IC50s of 9×10-8M (trypsin) and 2×10-7M (Cls) for the former and 3×10-8M (trypsin) and 2×10-7M (Cls) for the latter.

  多种amidinophenol衍生物（27-47）及其苯甲酸酯（4-26）被合成并评估了它们对胰蛋白酶、纤溶酶、激肽释放酶、凝血酶、Clr和Cls的抑制活性，以及体外补体介导的溶血作用。4-（β-脒基乙烯基）苯基4-胍基苯甲酸酯（15）和4-脒基-2-苯甲酰苯基4-胍基苯甲酸酯（26）被发现具有强大的抑制活性，前者的IC50值为9×10-8M（胰蛋白酶）和2×10-7M（Cls），后者的IC50值为3×10-8M（胰蛋白酶）和2×10-7M（Cls）。
• Phenol derivatives, processes for their preparation and pharmaceutical compositions containing them
  申请人：GLAXO GROUP LIMITED

  公开号：EP0028063A1

  公开（公告）日：1981-05-06

  Compounds are disclosed which are phenoxyalkoxyphenyl derivatives of general formula (I) wherein Y represents the group -A, -ZA or OZ1A where A represents a carboxylic acid group, a 5-1H-tetrazolyf ring or a N-5-1 H-tetrazolylcarboxamide group; Z represents a Ci-4 alkylene, C2-4 alkenylene or C2-4 alkynylene chain optionally substituted by one or more C1-3 alkyl groups and Z1 represents a C1-4 alkylene chain optionally substituted by one or more C1-3 alkyl groups; X represents a C1-10 carbon chain which may be saturated or unsaturated in the case of chains containing at least 4 carbon atoms, and may be substituted by a hydroxy group or by one or more C1-3 alkyl groups, which chain may be interrupted by a benzene ring which may be linked through its 1- and 2-, 1- and 3-, or 1- and 4-positions; R1 represents a hydrogen atom or a C1-6 alkyl group; R2 represents the group -COR6 where R6 represents a hydrogen atom, an aryl group or a C1-6 alkyl group which may be substituted by an aryl group; R3 represents a C1-6 alkyl group or a C3-6 alkenyl group; and R4 and R5 which may be the same or different, each represents a hydrogen atom, a halogen atom or a hydroxy, Ci-3 alkoxy, C1-6 alkyl, C3-C6 alkenyl, C1-3 alkanoyl, nitro or carboxylic acid group with the proviso that R4 and R5 cannot both be nitro, alkanoyl or carboxylic acid groups, and physologically acceptable salts thereof. The compounds are potent antagonists of the action of slow reacting substance of anaphylaxis and are thus indicated for use in the treatment of obstructive airways diseases such as asthma and hay fever and in skin afflictions.

  所公开的化合物是通式(I)的苯氧基烷氧基苯基衍生物 其中 Y 代表基团-A、-ZA 或 OZ1A，其中 A 代表羧酸基团、5-1H-四氮唑环或 N-5-1 H-四氮唑甲酰胺基团； Z 代表任选被一个或多个 C1-3 烷基取代的 Ci-4亚烷基、C2-4 亚烯基或 C2-4 亚炔基链，Z1 代表任选被一个或多个 C1-3 烷基取代的 C1-4 亚烷基链； X 代表 C1-10 碳链，可以是饱和的 或不饱和（如果链中至少含有 4 个碳原子），并可被羟基取代 或一个或多个 C1-3 烷基基团取代，该链可 可被一个苯环打断，该苯环可通过以下方式连接 1-位和 2-位、1-位和 3-位或 1-位和 4-位相连； R1 代表氢原子或 C1-6 烷基； R2 代表基团-COR6，其中 R6 代表氢原子、芳基或可被芳基取代的 C1-6 烷基； R3 代表 C1-6 烷基或 C3-6 烯基；以及 R4和R5可以相同或不同，各自代表氢原子、卤素原子或羟基、Ci-3烷氧基、C1-6烷基、C3-C6烯基、C1-3烷酰基、硝基或羧酸基团，但R4和R5不能都是硝基、烷酰基或羧酸基团，以及它们的物理上可接受的盐。 这些化合物是过敏性休克慢反应物质的强效拮抗剂，因此可用于治疗阻塞性呼吸道疾病，如哮喘和花粉症，以及皮肤病。