1-氟-4-[(1S)-1-异氰酸乙基]-苯 | 745783-74-8

• 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: 1-氟-4-[(1S)-1-异氰酸乙基]-苯
• 中文别名: (S)-(-)-1-(4-氟苯基)异氰酸乙酯
• 英文名称: 1-fluoro-4-((S)-1-isocyanato-ethyl)-benzene
• 英文别名: 1-fluoro-4-[(1S)-1-isocyanatoethyl]-benzene；(S)-1-(4-fluorophenyl)ethyl isocyanate；(S)-(-)-1-(4-Fluorophenyl)ethyl isocyanate；1-fluoro-4-[(1S)-1-isocyanatoethyl]benzene
• CAS: 745783-74-8
• 化学式: C₉H₈FNO
• 分子量: 165.167
• InChiKey: MUHCZVYPBWOTTJ-ZETCQYMHSA-N

物化性质

• 沸点：
  206.4±23.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 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：
  29.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 海关编码：
  2929109000
• 危险品运输编号：
  UN 2206

反应信息

• 作为反应物：
  描述：

  1-氟-4-[(1S)-1-异氰酸乙基]-苯 在 盐酸 、 水 作用下， 生成 (2S)-2-(4-fluorophenyl)propanamide
  参考文献：
  名称：

  Antidotes to anthrax lethal factor intoxication. Part 3: Evaluation of core structures and further modifications to the C2-side chain

  摘要：

  Four core structures capable of providing sub-nanomolar inhibitors of anthrax lethal factor (LF) were evaluated by comparing the potential for toxicity, physicochemical properties, in vitro ADME profiles, and relative efficacy in a rat lethal toxin (LT) model of LF intoxication. Poor efficacy in the rat LT model exhibited by the phenoxyacetic acid series (3) correlated with low rat microsome and plasma stability. Specific molecular interactions contributing to the high affinity of inhibitors with a secondary amine in the C2-side chain were revealed by X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.095
• 作为产物：
  描述：

  (2S)-2-(4-氟苯基)丙酸 在 sodium azide 、 三乙胺 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 1.5h， 生成 1-氟-4-[(1S)-1-异氰酸乙基]-苯
  参考文献：
  名称：

  Antidotes to anthrax lethal factor intoxication. Part 3: Evaluation of core structures and further modifications to the C2-side chain

  摘要：

  Four core structures capable of providing sub-nanomolar inhibitors of anthrax lethal factor (LF) were evaluated by comparing the potential for toxicity, physicochemical properties, in vitro ADME profiles, and relative efficacy in a rat lethal toxin (LT) model of LF intoxication. Poor efficacy in the rat LT model exhibited by the phenoxyacetic acid series (3) correlated with low rat microsome and plasma stability. Specific molecular interactions contributing to the high affinity of inhibitors with a secondary amine in the C2-side chain were revealed by X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.095

文献信息

• [EN] AUTOTAXIN INHIBITORY COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE L'AUTOTAXINE
  申请人：CANCER REC TECH LTD

  公开号：WO2016124939A1

  公开（公告）日：2016-08-11

  The present invention relates to compounds of formula I, wherein A1, A2, A3, R1, R2, R3, R4, R5, R6, L, Ar and Q are each as defined herein. The compounds of the present invention are inhibitors of autotaxin (ATX) enzyme activity. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions (e.g. fibrosis) in which ATX activity is implicated.

  本发明涉及式I的化合物，其中A1、A2、A3、R1、R2、R3、R4、R5、R6、L、Ar和Q分别如本文所定义。本发明的化合物是自体脂肪酶（ATX）酶活性的抑制剂。本发明还涉及制备这些化合物的方法，包括含有它们的药物组合物，以及它们在治疗增殖性疾病（如癌症）以及其他ATX活性所涉及的疾病或症状（例如纤维化）中的用途。
• [EN] NOVEL 4-(AZACYCLOALKYL)BENZENE-1,3-DIOL COMPOUNDS AS TYROSINASE INHIBITORS, PROCESS FOR THE PREPARATION THEREOF AND USE THEREOF IN HUMAN MEDICINE AND IN COSMETICS<br/>[FR] NOUVEAUX COMPOSÉS DE 4- (AZACYCLOALKYL) BENZENE-1, 3-DIOL UTILISÉS COMME INHIBITEURS DE LA TYROSINASE, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION EN MÉDICINE HUMAINE ET DANS LES COSMÉTIQUES
  申请人：GALDERMA RES & DEV

  公开号：WO2010063774A1

  公开（公告）日：2010-06-10

  The present invention relates to novel 4- (azacycloalkyl) benzene-1, 3-diol compounds corresponding to general formula (I) below: Formula (I) to the compositions containing same, to the process for the preparation thereof and to the use thereof in pharmaceutical or cosmetic compositions for use in the treatment or prevention of pigmentary disorders.

  本发明涉及与下面的一般式（I）相对应的新型4-(氮杂环烷基)苯-1,3-二酚化合物：式（I），以及含有这些化合物的组合物，其制备方法以及在制备用于治疗或预防色素紊乱的药用或化妆品组合物中的使用。
• T-type calcium channel blockers: spiro-piperidine azetidines and azetidinones—optimization, design and synthesis
  作者：Elizabeth M. Smith、Steve Sorota、Hyunjin M. Kim、Brian A. McKittrick、Terry L. Nechuta、Chad Bennett、Chad Knutson、Duane A. Burnett、Jane Kieselgof、Zheng Tan、Diane Rindgen、Terry Bridal、Xiaoping Zhou、Yu-Ping Jia、Zoe Dong、Debbie Mullins、Xiaoping Zhang、Tony Priestley、Craig C. Correll、Deen Tulshian、Michael Czarniecki、William J. Greenlee

  DOI：10.1016/j.bmcl.2010.06.012

  日期：2010.8

  A series of spiro-azetidines and azetidinones has been evaluated as novel blockers of the T-type calcium channel (CaV3.2) which is a new therapeutic target for the potential treatment of both inflammatory and neuropathic pain. Confirmation and optimization of the potency, selectivity and DMPK properties of leads will be described.

  已经评估了一系列螺氮杂环丁烷和氮杂环丁酮作为T型钙通道（Ca V 3.2）的新型阻滞剂，它是潜在治疗炎性和神经性疼痛的新治疗靶标。将描述和验证潜在性，选择性和DMPK特性的优化。
• [EN] NOVEL COMPOUNDS THAT ARE ERK INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS QUI SONT DES INHIBITEURS D'ERK
  申请人：MERCK SHARP & DOHME

  公开号：WO2013063214A1

  公开（公告）日：2013-05-02

  Disclosed are the ERK inhibitors of formula (1): and the pharmaceutically acceptable salts thereof. Also disclosed are methods of treating cancer using the compounds of formula (1).

  公开的是具有式(1)的ERK抑制剂及其药学上可接受的盐。还公开了使用式(1)的化合物治疗癌症的方法。
• Synthesis of 2-Pyrrolidinones by Palladium-Catalyzed [3+2] Cycloaddition of Isocyanates
  作者：Rolf Breinbauer、Marko Kljajic、Thomas Schlatzer

  DOI：10.1055/s-0037-1610692

  日期：2019.3

  Pd/DPEphos catalyzes the [3+2] cycloaddition of various alkyl isocyanates with 2-acetoxymethyl-3-allyltrimethylsilane as a synthetic equivalent of trimethylenemethane (TMM). Taking advantage of 2-acetoxymethyl-3-allyltrimethylsilane acting both as nucleophile as well as electrophile this reaction gives a convenient access to 5-ring lactams with an exocyclic alkene moiety. The formation of the β,γ-unsaturated

  Pd/DPEphos 催化各种异氰酸烷基酯与 2-乙酰氧基甲基-3-烯丙基三甲基硅烷的 [3+2] 环加成反应，作为三亚甲基甲烷 (TMM) 的合成等价物。利用 2-乙酰氧基甲基-3-烯丙基三甲基硅烷作为亲核试剂和亲电试剂，该反应可以方便地获得具有环外烯烃部分的 5 环内酰胺。β,γ-不饱和2-吡咯烷酮的形成没有烯烃异构化并且没有立体中心的差向异构化。机理研究表明异氰酸酯的初始 N-烯丙基化，然后是亲核闭环，提供所需的 2-吡咯烷酮。