氟乙酸甲酯 | 453-18-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 氟乙酸甲酯
• 中文别名: 甲基氟乙酸酯；2-氟乙酸甲酯
• 英文名称: methyl fluoroacetate
• 英文别名: Fluor-essigsaeure-methylester；methyl 2-fluoroacetate
• CAS: 453-18-9
• 化学式: C₃H₅FO₂
• mdl: MFCD00040096
• 分子量: 92.0699
• InChiKey: RJBYSQHLLIHSLT-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  1. 按照规格使用和贮存，不会发生分解，避免与氧化物接触。
  2. 其蒸汽和液体可能刺激眼睛和呼吸系统。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

ADMET

毒理性

• 毒性总结

甲基氟代醋酸（MFA）是一种流动液体。MFA是最有效的已知灭鼠剂之一。然而，它存在意外人类中毒的高风险。由于MFA具有极大的毒性，它在第二次世界大战开始时被考虑作为一种潜在的战争剂。人体研究：在摄入极小量后会出现恶心和呕吐。动物研究：在大多数动物中，它是一种致惊厥毒剂，会导致呼吸逐渐抑制。它阻断了酶aconitase，从而抑制了三羧酸循环。这种毒药作用迅速，且没有解毒剂。

IDENTIFICATION AND USE: Methyl fluoroacetate (MFA) is a mobile liquid. MFA is one of the most potent rodenticides known. However, it presents a high risk of accidental human poisoning. Because of MFA great toxicity, it came into consideration at the start of World War II as a potential warfare agent. HUMAN STUDIES: Nausea and vomiting following ingestion of very small amounts. ANIMAL STUDIES: In most animals it is a convulsant poison and causes progressive depression of respiration. It blocks the enzyme aconitase, thereby inhibiting the TCA cycle. This poison is quick-acting and has no antidote.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 紧急急救：确保已经进行了充分的中和。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按培训操作。根据需要执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或将其置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /酯类及相关化合物/

/SRP:/ Immediate fist aid: ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and Related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时进行治疗……监测休克，并在必要时进行治疗……对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛……不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的呕吐反射并不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……/酯类及相关化合物/

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Esters and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用带有球阀面罩装置的正压通气技术可能有益。监测心率和必要时治疗心律失常。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用乳酸钠林格氏液。注意液体过载的迹象。对于伴有低血容量迹象的低血压，谨慎输注液体。如果病人在正常血容量时出现低血压，考虑使用血管加压药。注意液体过载的迹象...。考虑使用药物治疗肺水肿...。使用丙美卡因氢氯化物协助眼部冲洗...。/酯类和相关化合物/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/体征和症状/ 通过摄入极小量的人类系统性影响；恶心或呕吐。

/SIGNS AND SYMPTOMS/ Human systemic effects by ingestion of very small amounts; nausea or vomiting.

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

由氯乙酸甲酯与氟化钾反应而得。

合成制备方法

同样地，也是通过氯乙酸甲酯与氟化钾的反应得到的。

用途简介

1. 氟乙酸甲酯是生产氟啶酸、环丙氟啶酸、5-氟尿嘧啶、氟苷、喃氟啶、双呋啶5-氟-4-羟基嘧啶等药物的基本原料，也是农药和香料的中间体。
2. 它还用作医药、农药和染料的中间体。

用途

1. 氟乙酸甲酯为生产氟啶酸、环丙氟啶酸、5-氟尿嘧啶、氟苷、喃氟啶、双呋啶5-氟-4-羟基嘧啶等药物的基本原料，也是农药和香料的中间体。
2. 它还用作医药、农药和染料的中间体。

反应信息

• 作为反应物：
  描述：

  氟乙酸甲酯 在 barytes 作用下， 生成 氟乙酸
  参考文献：
  名称：

  Swarts, Bulletin de la Societe Chimique de France, 1896, vol. <3>15, p. 1134

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙酸甲酯 在 potassium fluoride 、 乙酰丙酮 作用下， 生成 氟乙酸甲酯
  参考文献：
  名称：

  Olah; Pavlath, Acta Chimica Academiae Scientiarum Hungaricae, 1953, vol. 3, p. 203,206

  摘要：

  DOI：

文献信息

• Synthesis and antibacterial activity evaluation of C-5 side chain modified analogues of FYL-66, a potential agent against methicillin-resistant Staphylococcus aureus
  作者：Xiaoyan Yang、Zicheng Li、Zhenling Wang、Zitai Sang、Haiyue Long、Jianying Tang、Tao Yang、Yuanyuan Liu、Youfu Luo

  DOI：10.1039/c5md00101c

  日期：——

  as new chemical entities (NCE) with pronounced in vitro and in vivo activities against MRSA and MSSA. Aiming to explore the structure–activity relationship at the C-5 side chain of FYL-66 and find novel potential antibacterial agents, a series of analogues were designed and synthesized by the introduction of various substituents at the C-5 position of the oxazolidinone ring. Their in vitro antibacterial

  FYL-66及其盐酸盐FYL-67已被鉴定为对MRSA和MSSA具有明显的体外和体内活性的新化学实体（NCE）。为了探索FYL-66 C-5侧链的结构-活性关系并发现新型潜在的抗菌剂，通过在恶唑烷酮环的C-5位置引入各种取代基，设计并合成了一系列类似物。还通过微量稀释法评估了它们的体外抗菌活性。新颖的化合物31，33，37，39和40在MIC值为2-4μgmL -1的范围内显示出有效的抗菌活性。发现二氟取代的类似物40在抗菌功效，理化性质和安全性之间具有良好的平衡。在鼠类全身感染模型中，类似物40显示出与FYL-66相当的保护率。绝对生物利用度为40其半衰期为8.87±3.25 h（po）和5.40±1.40 h（iv），为89.6％。同时，我们的发现表明FYL-66的C-5侧链的重要性，并暗示具有小C-5取代基的模拟乙酰胺基的化合物表现出更好的活性。同样令人感兴趣的是，FYL-66，Li
• Synthesis and immunological evaluation of MUC1 glycopeptide conjugates bearing N-acetyl modified STn derivatives as anticancer vaccines
  作者：An Xiao、Xiu-Jing Zheng、Chengcheng Song、Yue Gui、Chang-Xin Huo、Xin-Shan Ye

  DOI：10.1039/c6ob01092j

  日期：——

  problem. To solve this problem, several STn derivatives with N-acetyl modifications were synthesized and incorporated into a 20-amino acid MUC1 tandem repeat sequence. The modified STn-MUC1 glycopeptides were further connected to a carrier protein keyhole limpet hemocyanin (KLH). The immunological effects of these synthetic vaccine conjugates were evaluated using the BALB/c mouse model. The results showed

  糖蛋白MUC1是抗肿瘤疫苗开发的有吸引力的靶标。但是，MUC1的免疫原性仍然很弱。为了解决该问题，合成了几种具有N-乙酰基修饰的STn衍生物，并将其掺入20个氨基酸的MUC1串联重复序列中。修饰的STn-MUC1糖肽进一步与载体蛋白匙孔戚血蓝蛋白（KLH）连接。使用BALB / c小鼠模型评估了这些合成疫苗偶联物的免疫学作用。结果表明，疫苗V2引起与天然STn-MUC1抗原交叉反应的抗体的更高滴度。此外，引起的抗血清与STn-MUC1抗原阳性的肿瘤细胞反应，表明碳水化合物抗原修饰策略可能具有克服天然MUC1糖肽弱免疫原性的潜力。
• SIALIC ACID (A-(2-6))-D-AMINOPYRANOSE DERIVATIVES, SYNTHESIS METHODS AND USES THEREOF
  申请人：Ye Xinshan

  公开号：US20130079291A1

  公开（公告）日：2013-03-28

  N-acyl modified sialic acid (α-(2→6))-D-aminopyranose derivatives, their synthesis methods and uses are disclosed. Sialic acid (α-(2→6))-D-aminopyranose derivatives represented by formula 1 are synthesized by using D-aminogalactose (glucose) and sialic acid as raw materials, which are coupled with carrier proteins or polypeptides to obtain glycoprotein (glycopeptide) conjugates. Acetyl is replaced by derivative acyl in the structures of said compounds, therefore the compounds show good activity in antitumor vaccines.

  N-酰基修饰唾液酸（α-(2→6))-D-氨基吡喃糖衍生物，其合成方法和用途已被披露。通过使用D-氨基半乳糖（葡萄糖）和唾液酸作为原料，合成了由式1表示的唾液酸（α-(2→6))-D-氨基吡喃糖衍生物，这些衍生物与载体蛋白或多肽偶联以获得糖蛋白（糖肽）共轭物。在这些化合物的结构中，乙酰基被衍生酰基所取代，因此这些化合物在抗肿瘤疫苗中表现出良好的活性。
• Improvement of the immune efficacy of carbohydrate vaccines by chemical modification on the GM3 antigen
  作者：Xiu-Jing Zheng、Fan Yang、Mingwei Zheng、Chang-Xin Huo、Ye Zhang、Xin-Shan Ye

  DOI：10.1039/c5ob00405e

  日期：——

  N-modified GM3 glycoconjugates improved the efficiency of the vaccination without the combination of metabolic oligosaccharide engineering technology.

  N-修饰的GM3糖结合物提高了疫苗的效率，而无需结合代谢寡糖工程技术。
• Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals
  作者：Yoshihiro Inamoto、Yuta Kaga、Yoshihiro Nishimoto、Makoto Yasuda、Akio Baba

  DOI：10.1002/chem.201403734

  日期：2014.9.8

  sequential addition of silyl cyanide and ketene silyl acetals to esters was achieved by a gallium trihalide catalyst to produce β‐cyano‐β‐siloxy esters. This is the first example of the sequential addition of two different carbon nucleophiles to esters. The employment of lactones provided α,α‐disubstituted cyclic ethers with a cyano group and an ester moiety. A variety of esters and lactones are applicable

  通过三卤化镓催化剂可将甲硅烷基氰化物和乙烯酮甲硅烷基缩醛顺序添加到酯中，以生产β-氰基-β-甲硅烷氧基酯。这是将两个不同的碳亲核试剂顺序加成到酯中的第一个例子。内酯的使用为α，α-二取代的环状醚提供了一个氰基和一个酯基。多种酯和内酯可用于该反应系统。

表征谱图