异氰酸乙酯 | 109-90-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 异氰酸乙酯
• 中文别名: 異氰酸乙酯；乙基异氰酸酯;；异氰酸乙基酯；乙基异氰酸酯
• 英文名称: ethyl isocyanate
• 英文别名: isocyanatoethane
• CAS: 109-90-0
• 化学式: C₃H₅NO
• mdl: MFCD00002042
• 分子量: 71.0788
• InChiKey: WUDNUHPRLBTKOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  60 °C(lit.)
• 密度：
  0.898 g/mL at 25 °C(lit.)
• 闪点：
  20 °F
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Ethyl isocyanate appears as a colorless liquid. Less dense than water and insoluble in water. May irritate skin, eyes, and mucous membranes. May be lethal by Inhalation . Used to make pharmaceuticals and pesticides.
• 颜色/状态：
  Liquid
• 气味：
  Pungent smelling
• 蒸汽密度：
  2.45 (Air = 1)
• 蒸汽压力：
  200 mm Hg at 25 °C (est)
• 旋光度：
  Specific optical rotation = 1.3808 at 20 °C/D
• 分解：
  When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
• 燃烧热：
  424.5 kcal (liquid)
• 折光率：
  Index of refraction: 1.3808 at 20 °C/D
• 稳定性/保质期：
  避免与潮湿的空气接触，禁止与水、醇类、强碱、酸类以及强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

一般来说，活性异氰酸酯可以与含有氨基、醇基或巯基的生物分子以及水发生反应。虽然在像肺部这样的水环境中理论上可能发生水解，但测量结果显示，与芳香族异氰酸酯相比，烷基异氰酸酯对此类水解相对抵抗。

... Reactive isocyanates in general, can react with biological molecules containing amino, alcohol, or sulfhydryl groups, as well as with water. While hydrolysis in an aqueous environment, such as the lung, is theoretically possible, measurements show that alkyl isocyanates are relatively resistant (compared to arylisocyanates) to such hydrolysis.

来源:Hazardous Substances Data Bank (HSDB)

代谢

异氰酸酯...形成不稳定的谷胱甘肽结合物，它们可以从这些结合物中被释放出来。/异氰酸酯/

Isocyanates ... form labile glutathione conjugates from which they can be released. /Isocyanate/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。 Lacrimator (Lachrymator) - 刺激眼睛并引起流泪的物质。 Skin Sensitizer - 可以诱导皮肤产生过敏反应的剂。 Toxic Pneumonitis - 由于吸入金属烟雾或有毒气体和蒸气引起的肺部炎症。

Dermatotoxin - Skin burns. Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears. Skin Sensitizer - An agent that can induce an allergic reaction in the skin. Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 毒性数据

LCLo（大鼠）= 240 毫克/立方米/6小时

LCLo (rat) = 240 mg/m3/6h

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

氯乙基异氰酸酯、乙基异氰酸酯和氰酸钠对大鼠肝脏和肝肿瘤摄取同位素标记的胸腺嘧啶、亮氨酸和H2O的影响进行了比较。数据显示，碳酰胺化剂可能具有一种共同的特性，即在携带肿瘤的大鼠肝脏中影响较小或无作用的情况下，抑制肝肿瘤中化合物的摄取。组织之间的区别可能部分是通过肿瘤循环的影响来介导的，当离体细胞在体外研究中则不太明显。碳酰胺化剂对亮氨酸和H2O摄取的优先抑制效应在小鼠肝肿瘤中也观察到了，但与大鼠肝肿瘤相比效果不那么显著。

The effects of 2-chloroethylisocyanate, ethylisocyanate and sodium cyanate on the uptake of isotope-labeled thymidine, leucine and H2O were compared in rat liver and hepatomas. The data suggested that carbamoylating agents may have a common property of inhibiting uptake of compounds in hepatomas under conditions in which there is a smaller effect or no action in the liver of tumor-bearing rats. The distinction between tissues may have been mediated, in part, through effects on tumor circulation and was less apparent when isolated cells were studied in vitro. Preferential inhibitory effects of carbamoylating agents on the uptake of leucine and H2O were also observed with a murine hepatoma, but they were not as great as with rat hepatomas.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

如果这种化合物接触到眼睛，请立即用大量清水冲洗眼睛，同时提起上眼睑和下眼睑。立即就医。/甲基异氰酸酯/

If this compound comes into contact with the eyes, wash the eyes immediately with large amounts of water, lifting both the upper and lower lids. Acquire medical attention immediately. /Methyl isocyanate/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

非心源性肺水肿和支气管痉挛是异氰酸酯暴露最直接的严重临床后果。症状明显的患者应该接受吸氧、呼吸支持并建立静脉通道。哮喘的治疗包括吸入拟交感神经药物（沙丁胺醇、间羟异丙肾上腺素）、静脉注射茶碱、parenteral拟交感神经药物（肾上腺素、特布他林）和激素。/异氰酸酯/

Noncardiogenic pulmonary edema and bronchospasm are the most immediate serious clinical consequences of isocyanate exposure. Markedly symptomatic patients should receive oxygen, ventilatory support, and an intravenous line. Treatment for asthma includes inhaled sympathomimetics (salbutamol, metaproterenol), intravenous theophylline, parenteral sympathomimetics (epinephrine, terbutaline), and steroids. /Isocyanates/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  3.1
• 危险品标志：
  F,T
• 安全说明：
  S16,S26,S36/37/39,S45
• 危险类别码：
  R20/21,R42,R36/37/38,R11,R25
• WGK Germany：
  3
• 海关编码：
  29291090
• 危险品运输编号：
  UN 2481 3/PG 1
• 危险类别：
  3.1
• RTECS号：
  NQ8825000
• 包装等级：
  I
• 储存条件：
  储存于阴凉、干燥、通风良好的库房中。远离火种、热源，库温不宜超过30℃。保持容器密封，并与氧化剂、酸类、碱类、醇类及食用化学品分开存放，切忌混储。使用防爆型照明和通风设施，禁止使用易产生火花的机械设备和工具。储区内应备有泄漏应急处理设备和合适的收容材料。

SDS

第一部分：化学品名称

制备方法与用途

化学性质：

• 无色液体，沸点为60℃，相对密度为0.898，闪点为-6℃。

类别：易燃液体

毒性分级：高毒

急性毒性：静注-小鼠 LD50 值为56毫克/公斤

爆炸物危险特性：与空气混合可爆炸

可燃性危险特性：易燃

储运特性：

• 库房应保持通风、低温和干燥环境
• 须与氧化剂分开储存和运输

灭火剂：

• 干粉、二氧化碳、1211 和泡沫

反应信息

• 作为反应物：
  描述：

  异氰酸乙酯 在 硫化氢 作用下， 生成 羰基硫
  参考文献：
  名称：

  Ladenburg, Chemische Berichte, 1869, vol. 2, p. 30

  摘要：

  DOI：
• 作为产物：
  描述：

  丙酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.25h， 生成 异氰酸乙酯
  参考文献：
  名称：

  Structure-based drug design and potent anti-cancer activity of tricyclic 5:7:5-fused diimidazo[4,5-d:4′,5′-f][1,3]diazepines

  摘要：

  Judicial structural modifications of 5: 7-fused ring-expanded nucleosides (RENs), based on molecular modeling studies with one of its known targets, human RNA helicase (hDDX3), led to the lead, novel, 5:7-5-fused tricyclic heterocycle (1). The latter exhibited promising broad-spectrum in vitro anti-cancer activity against a number of cancer cell lines screened. This paper describes our systematic, albeit limited, structure-activity relationship (SAR) studies on this lead compound, which produced a number of analogs with broad-spectrum in vitro anti-cancer activities against lung, breast, prostate, and ovarian cancer cell lines, in particular compounds 15i, 15j, 15m and 15n which showed IC50 values in submicromolar to micromolar range, and are worthy of further explorations. The SAR data also enabled us to propose a tentative SAR model for future SAR efforts for ultimate realization of optimally active and minimally toxic anti-cancer compounds based on the diimidazo[4,5-d:4',5'-f][1,3]diazepine structural skeleton of the lead compound 1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.050
• 作为试剂：
  描述：

  methylenephosphanyl phosphorane 在 异氰酸乙酯 作用下， 生成
  参考文献：
  名称：

  Methylenephosphinophosphoranes. Unusual Addition Reaction in Organophosphorus Chemistry

  摘要：

  DOI：

  10.1080/10426509608046306

文献信息

• [EN] THIOPHENE DERIVATIVES FOR THE TREATMENT OF DISORDERS CAUSED BY IGE<br/>[FR] DÉRIVÉS DE THIOPHÈNE POUR LE TRAITEMENT DE TROUBLES PROVOQUÉS PAR IGE
  申请人：UCB BIOPHARMA SRL

  公开号：WO2019243550A1

  公开（公告）日：2019-12-26

  Thiophene derivatives of formula (I) and a pharmaceutically acceptable salt thereof are provided. These compounds have utility for the treatment or prevention of disorders caused by IgE, such as allergy, type 1 hypersensitivity or familiar sinus inflammation.

  提供了公式（I）的噻吩衍生物及其药用可接受的盐。这些化合物对于治疗或预防由IgE引起的疾病具有用途，如过敏、1型超敏反应或家族性鼻窦炎。
• Synthesis of Thiocarbamates from Thiols and Isocyanates Under Catalyst- and Solvent-Free Conditions
  作者：Barahman Movassagh、Mohammad Soleiman-Beigi

  DOI：10.1007/s00706-007-0762-7

  日期：2008.2

  A simple and efficient procedure was developed for the synthesis of S -alkyl (aryl) thiocarbamates under solvent-free conditions without the use of a catalyst. The significant features of this protocol are (a) operational simplicity, (b) mild reaction conditions, (c) short reaction times, (d) solvent-free conditions, and (e) high product yields.

  开发了一种简单有效的方法，用于在无溶剂条件下不使用催化剂合成 S- 烷基（芳基）硫代氨基甲酸酯。该方案的显着特征是（a）操作简便，（b）反应条件温和，（c）反应时间短，（d）无溶剂条件和（e）产品收率高。
• 1-Amino 1H-imidazoquinolines
  申请人：Griesgraber W. George

  公开号：US20050054640A1

  公开（公告）日：2005-03-10

  1-Amino 1H-imidazoquinoline compounds, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  1-氨基1H-咪唑喹啉化合物，含有该化合物的药物组合物，中间体，以及制备这些化合物的方法和将这些化合物用作免疫调节剂的方法，用于调节动物体内细胞因子生物合成，并用于治疗包括病毒性和肿瘤性疾病在内的疾病。
• [EN] SUBSTITUTED BENZYLAMINE COMPOUNDS, THEIR USE IN MEDICINE, AND IN PARTICULAR THE TREATMENT OF HEPATITIS C VIRUS (HCV) INFECTION<br/>[FR] COMPOSÉS DE BENZYLAMINE SUBSTITUÉS, LEUR UTILISATION EN MÉDECINE, EN PARTICULIER DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE C (VHC)
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2013064538A1

  公开（公告）日：2013-05-10

  The invention provides compounds of the formula (I): or a salt, N-oxide or tautomer thereof, wherein A is CH, CF or nitrogen; E is CH, CF or nitrogen; and R0 is hydrogen or C1-2 alkyl; R1a is selected from CONH2; CO2H; an optionally substituted acyclic C1-8 hydrocarbon group; and an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1, 2, 3 or 4 are heteroatom ring members selected from O, N and S; R2 is selected from hydrogen and a group R2a; R2a is selected from an optionally substituted acyclic d-8 hydrocarbon group; an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1 or 2 ring members are heteroatom ring members selected from O, N and S; and an optionally substituted bicyclic heterocyclic group of 9 or 10 ring members, of which 1 or 2 ring members are nitrogen atoms; wherein at least one of R1 and R2 is other than hydrogen; R3 is an optionally substituted 3- to 10-membered monocyclic or bicyclic carbocyclic or heterocyclic ring containing 0, 1, 2 or 3 heteroatom ring members selected from N, O and S; R4a is selected from halogen; cyano; C1-4 alkyl optionally substituted with one or more fluorine atoms; C1-4 alkoxy optionally substituted with one or more fluorine atoms; hydroxy-C1-4 alkyl; and C1-2 alkoxy-C1-4 alkyl; R5 is selected from hydrogen and a substituent R5a; and R5a is selected from C1-2 alkyl optionally substituted with one or more fluorine atoms; C1-3 alkoxy optionally substituted with one or more fluorine atoms; halogen; cyclopropyl; cyano; and amino, The compounds have activity against hepatitis C virus and can be used in the prevention or treatment of hepatitis C viral infections.

  该发明提供了以下式（I）的化合物，或其盐、N-氧化物或互变异构体，其中A为CH、CF或氮；E为CH、CF或氮；R0为氢或C1-2烷基；R1a选自CONH2；CO2H；一个可选择取代的非环状C1-8碳氢化合物基团；以及一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1、2、3或4个是从O、N和S中选择的杂原子环成员；R2选自氢和一个基团R2a；R2a选自一个可选择取代的非环状d-8碳氢化合物基团；一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1或2个环成员是从O、N和S中选择的杂原子环成员；以及一个可选择取代的含有9或10个环成员的双环杂环基团，其中1或2个环成员是氮原子；其中R1和R2中至少一个不是氢；R3选自一个可选择取代的含有0、1、2或3个从N、O和S中选择的杂原子环成员的3至10个成员的单环或双环碳环或杂环环；R4a选自卤素；氰基；C1-4烷基，可选择取代一个或多个氟原子；C1-4烷氧基，可选择取代一个或多个氟原子；羟基-C1-4烷基；和C1-2烷氧基-C1-4烷基；R5选自氢和一个取代基R5a；R5a选自C1-2烷基，可选择取代一个或多个氟原子；C1-3烷氧基，可选择取代一个或多个氟原子；卤素；环丙基；氰基；和氨基。这些化合物对丙型肝炎病毒具有活性，并可用于预防或治疗丙型肝炎病毒感染。
• [EN] OXAZOLIDINONE COMPOUNDS AND METHODS OF USE THEREOF AS ANTIBACTERIAL AGENTS<br/>[FR] COMPOSÉS OXAZOLIDINONE ET PROCÉDÉS D'UTILISATION DE CES DERNIERS EN TANT QU'AGENTS ANTIBACTÉRIENS
  申请人：MERCK SHARP & DOHME

  公开号：WO2017066964A1

  公开（公告）日：2017-04-27

  The present invention relates to oxazolidinone compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, E, and R1 are as defined herein. The present invention also relates to compositions which comprise at least one oxazolidinone compound of the invention. The invention also provides methods for inhibiting growth of mycobacterial cells as well as a method of treating mycobacterial infections by Mycobacterium tuberculosiscomprising administering a therapeutically effective amount of an oxazolidinone of the invention and/or apharmaceutically acceptable salt thereof, or a composition comprising such compound and/or salt.

  本发明涉及式(I)的噁唑烷酮化合物及其药学上可接受的盐，其中A、E和R1如本文所定义。本发明还涉及包含本发明至少一种噁唑烷酮化合物的组合物。该发明还提供了抑制分枝杆菌细胞生长的方法，以及通过给予治疗有效量的本发明的噁唑烷酮和/或其药学上可接受的盐，或包含该化合物和/或盐的组合物来治疗结核分枝杆菌感染的方法。

表征谱图