全氟辛基磺酰胺 | 754-91-6

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 中文名称: 全氟辛基磺酰胺
• 中文别名: 全氟烷基磺酰胺；全氟辛烷磺酰胺；全氟代辛烷磺酰胺；FC-99
• 英文名称: heptadecafluoro-octane-1-sulfonic acid amide
• 英文别名: Perfluorooctanesulfonamide；1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8 heptadecafluoro-n-octane sulfonamide；1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide；heptadecafluorooctane sulfonamide；heptadecafluorooctanesulfonamide；perfluoro-n-octane sulfonamide
• CAS: 754-91-6
• 化学式: C₈H₂F₁₇NO₂S
• mdl: MFCD03094345
• 分子量: 499.148
• InChiKey: RRRXPPIDPYTNJG-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  227.2±50.0 °C(Predicted)
• 密度：
  1.7595 (estimate)
• 溶解度：
  可溶于丙酮（少量）、甲醇（少量）
• 蒸汽压力：
  0.31 mm Hg at 25 °C (est)
• 分解：
  When heated to decompostion it emits toxic vapors of /oxides of sulfur, oxides of nitrogen, and fluorine/.

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  20

ADMET

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，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。 /毒物A和B/

/SRP:/ Immediate first 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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/

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（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，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，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预期癫痫发作，如有必要，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0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

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、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。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0.9%的生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/BIOMONITORING/ /研究人员/研究了孕妇血清中全氟化合物（PFCs）的浓度及其在1996年至2004年间瑞典母乳中的时间趋势。分析了来自瑞典12名初产妇的配对母乳和血清样本，以及从1996年至2004年的混合母乳样本（每年25-90名女性）。在血清样本中检测到了8种PFCs，其中5种在母乳样本中的浓度也超过了检测限。全氟辛烷磺酸（PFOS）和全氟己烷磺酸（PFHxS）在所有母乳样本中均有检出，平均浓度分别为0.201 ng/mL和0.085 ng/mL。全氟辛烷磺酰胺（PFOSA）、全氟辛酸（PFOA）和全氟壬酸（PFNA）检出频率较低。孕妇血清中的总PFC浓度为32 ng/mL，相应的母乳浓度为0.34 ng/mL。PFOS的母乳水平平均为相应血清水平的1%。血清浓度增加与PFOS（r(2)=0.7）和PFHxS（r(2)=0.8）的母乳浓度增加之间存在强相关性。1996年至2004年间，混合母乳样本中的PFOS和PFHxS水平相对稳定，总变异系数分别为20%和32%。在这项研究中，通过哺乳转移到婴儿体内的PFC总量大约为每天200 ng。哺乳是婴儿接触全氟化合物的显著来源，因此需要为风险评估设定参考浓度。

/BIOMONITORING/ /Reaserchers/ studied occurrence and levels of PFCs in human milk in relation to maternal serum together with the temporal trend in milk levels between 1996 and 2004 in Sweden. Matched, individual human milk and serum samples from 12 primiparous women in Sweden were analyzed together with composite milk samples (25-90 women/year) from 1996 to 2004. Eight PFCs were detected in the serum samples, and five of them were also above the detection limits in the milk samples. Perfluorooctanesulfonate (PFOS) and perfluorohexanesulfonate (PFHxS) were detected in all milk samples at mean concentrations of 0.201 ng/mL and 0.085 ng/mL, respectively. Perfluorooctanesulfonamide (PFOSA), perfluorooctanoic acid (PFOA), and perfluorononanoic acid (PFNA) were detected less frequently. The total PFC concentration in maternal serum was 32 ng/mL, and the corresponding milk concentration was 0.34 ng/mL. The PFOS milk level was on average 1% of the corresponding serum level. There was a strong association between increasing serum concentration and increasing milk concentration for PFOS (r(2) = 0.7) and PFHxS (r(2) = 0.8). PFOS and PFHxS levels in composite milk samples were relatively unchanged between 1996 and 2004, with a total variation of 20 and 32% coefficient of variation, respectively. The calculated total amount of PFCs transferred by lactation to a breast-fed infant in this study was approximately 200 ng/day. Lactation is a considerable source of exposure for infants, and reference concentrations for hazard assessments are needed.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验动物：发育或生殖毒性/全氟辛烷磺酸盐（PFOS）在野生动物和人类中广泛存在，具有环境和代谢稳定性。怀孕的Sprague-Dawley大鼠在GD 19-20天口服接受了0、25或50 mg/kg/天的PFOS/K+。准备了GD 21胎儿的肺和新生儿的肺进行组织学和形态测量。救援实验包括与PFOS共同给予地塞米松或视黄醇棕榈酸酯。使用质谱法研究了GD 21羊水和新生儿肺中的肺表面活性物质。在PND 0的肺上进行了微阵列分析。组织学上，PFOS暴露的新生儿肺泡壁比对照组厚。实质组织：小气道的比例增加，提示未成熟。救援研究无效。PFOS不影响磷脂浓度和分子种类。微阵列分析没有检测到肺泡分化标志物的变化。PFOS暴露的新生儿肺的形态学变化提示未成熟，但救援剂失败和正常的肺表面活性物质轮廓表明，PFOS处理的新生儿所观察到的呼吸困难并非由于肺未成熟。

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Perfluorooctane sulfonate (PFOS), found widely in wildlife and humans, is environmentally and metabolically stable. Pregnant Sprague-Dawley rats received 0, 25, or 50 mg/kg/day PFOS/K+ orally on GD 19-20. Lungs from GD 21 fetuses and neonates were prepared for histology and morphometry. Rescue experiments included co-administration of dexamethasone or retinyl palmitate with PFOS. Pulmonary surfactant was investigated with mass spectrometry in GD 21 amniotic fluid and neonatal lungs. Microarray analysis was carried out on PND 0 lungs. Histologically, alveolar walls were thicker in lungs of PFOS-exposed newborns compared to controls. The ratio of solid tissue:small airway was increased, suggesting immaturity. Rescue studies were ineffective. Phospholipid concentrations and molecular speciation were unaffected by PFOS. No changes in markers of alveolar differentiation were detected by microarray analysis. Morphometric changes in lungs of PFOS exposed neonates were suggestive of immaturity, but the failure of rescue agents and normal pulmonary surfactant profile indicate that the labored respiration and mortality observed in PFOS-treated neonates was not due to lung immaturity.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2942000000
• 安全说明：
  S22,S24/25
• WGK Germany：
  3

制备方法与用途

用途
用于合成氟表面活性剂，并引入其他基团到氮原子上。

用途
用于治疗溶血性链球菌、肺炎球菌及脑膜炎球菌等感染。对胺磺类药物过敏者忌用，肾功能减退者慎用。

反应信息

• 作为反应物：
  描述：

  全氟辛基磺酰胺 在 extracellular enzyme solution of Acinetobacter sp. strain M 、 Tween 20 作用下， 以 aq. buffer 为溶剂， 反应 12.0h， 生成 1,1,2,2,3,3,4,4-Octafluorobutane-1-sulfonamide
  参考文献：
  名称：

  不动杆菌属细菌降解全氟辛烷磺酰胺 M及其细胞外酶。

  摘要：

  不动杆菌属。从中国江苏省受污染的土壤样品中分离出的M菌株能够有效降解全氟辛烷磺酰胺（PFOSA）。通过离子色谱法检测了从PFOSA降解释放的氟阴离子（F-），其与不动杆菌的生长曲线呈正相关。通过GC分析评估，菌株M的PFOSA降解效率约为27％。结果表明，酶位于不动杆菌属的细胞外部。菌株M催化了PFOSA的降解。这进一步表明了PFOSA降级的可能新的（多步/路径）机制。这表明不动杆菌属菌株M的细胞外酶优先裂解碳-碳和碳-氟键，而不破坏碳-硫键。不动杆菌的生长条件 在2000 mg L-1的PFOSA和0.5％（v / v）的Tween-20存在下，在30°C和pH 7.0下优化菌株M。发现最佳PFOSA降解时间为12 h，通过GC分析测定，菌株M中的细胞外酶的降解效率为76％。该结果可为全氟有机化合物，如全氟辛烷（C8）的衍生物的生物降解提供潜在的应用。

  DOI：

  10.1002/asia.201900638
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氨 作用下， 生成 全氟辛基磺酰胺
  参考文献：
  名称：

  Perfluorinated Brønsted 'Superacids': Powerful Catalysts for the Preparation of Vitamin E

  摘要：

  工业合成（全反式）-α-生育酚（合成维生素E）的关键步骤是三甲基对羟基苯醌与C20组分异叶醇的缩合反应。对于这种弗里德尔-克拉夫茨类型的反应，全氟化的NH-和CH-酸性化合物（全氟烷基（芳基）磺酰亚胺和甲亚胺）已被应用作为优秀的催化剂，最好是在两相溶剂体系中。

  DOI：

  10.2533/000942904777678181

文献信息

• Synthesis and Structural Aspects of<i>N</i>-Triflylphosphoramides and Their Calcium Salts-Highly Acidic and Effective Brønsted Acids
  作者：Magnus Rueping、Boris J. Nachtsheim、René M. Koenigs、Winai Ieawsuwan

  DOI：10.1002/chem.201001438

  日期：2010.11.22

  emerged as a new class of potent Brønsted acid catalysts. In this paper we describe the efficient synthesis of various BINOL‐based N‐triflylphosphoramides and their calcium salts. Furthermore, X‐ray crystal structure analysis combined with energy‐dispersive X‐ray spectroscopy (EDX) measurements confirmed that the synthesised chiral N‐triflylphosphoramides are highly acidic metal‐free catalysts.

  最近，基于1,1'-二-2-萘酚（BINOL）的N-三氟磷酰胺已成为一类新型的强布朗斯泰酸催化剂。在本文中，我们描述了各种基于BINOL的N-三氟磷酰胺及其钙盐的有效合成。此外，X射线晶体结构分析与能量色散X射线光谱（EDX）测量相结合证实，合成的手性N-三氟磷酰胺是高度酸性的无金属催化剂。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• Synthesis of symmetric and dissymetric bisperfluoroalkanesulfonylimides and evaluation of their inhibition on bovine carbonic anhydrase
  作者：Zohra Benfodda、Franck Guillen、Hubert Blancou

  DOI：10.1002/hc.20452

  日期：2008.7

  describes a synthesis of symmetric and dissymmetric bis[(perfluoroalkane)-sulfonyl]imides by the reaction of the sodium salt of perfluoroalkanesulfonamide RFSO2NH−Na+ (RF = C4F9, C6F13, C8F17) with hexamethyldisilazane and perfluoroalkanesulfonylfluoride RFSO2F (RF = C4F9, C6F13, C8F17). They are obtained, in two steps, in moderate overall yield. Moreover, this paper provides a study of their inhibition on

  本研究描述了通过全氟烷烃磺酰胺 RFSO2NH−Na+（RF = C4F9、C6F13、C8F17）的钠盐与六甲基二硅氮烷和全氟烷烃磺酰氟 RFSO2F（RF = C4F39 , C8F17)。它们分两步以中等总产率获得。此外，本文还研究了它们对牛碳酸酐酶的抑制作用。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:542–548, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20452
• Scalable and Highly Diastereo- and Enantioselective Catalytic Diels–Alder Reaction of α,β-Unsaturated Methyl Esters
  作者：Tim Gatzenmeier、Mathias Turberg、Diana Yepes、Youwei Xie、Frank Neese、Giovanni Bistoni、Benjamin List

  DOI：10.1021/jacs.8b07092

  日期：2018.10.10

  Despite tremendous advances in enantioselective catalysis of the Diels-Alder reaction, the use of simple α,β-unsaturated esters, one of the most abundant and useful class of dienophiles, is still severely limited in scope due to their low reactivity. We report here a catalytic asymmetric Diels-Alder methodology for a large variety of α,β-unsaturated methyl esters and different dienes based on extremely

  尽管在 Diels-Alder 反应的对映选择性催化方面取得了巨大进展，但简单的 α,β-不饱和酯（最丰富和最有用的亲双烯体之一）的使用范围仍然受到严重限制，因为它们的反应性低。我们在此报告了一种催化不对称 Diels-Alder 方法，用于基于极易反应的亚氨基二磷酰亚胺 (IDPi) 路易斯酸的多种 α,β-不饱和甲酯和不同的二烯。来自基于精确域的局部对自然轨道耦合簇 (DLPNO-CCSD(T)) 计算的机械见解使催化剂控制和立体化学结果合理化。
• Chiral Brønsted Acid as a True Catalyst: Asymmetric Mukaiyama Aldol and Hosomi–Sakurai Allylation Reactions
  作者：Masahiro Sai、Hisashi Yamamoto

  DOI：10.1021/jacs.5b04168

  日期：2015.6.10

  diastereo- and enantioselective Mukaiyama aldol reaction catalyzed by a new chiral Brønsted acid, N-(perfluorooctanesulfonyl)thiophosphoramide, is described. The perfluorooctyl substituent on the sulfonyl group of the catalyst plays an essential role in the stereoselection. The catalyst also allows the asymmetric Hosomi-Sakurai allylation, which has been considerably challenging due to the low reactivity of

  描述了由新的手性布朗斯台德酸 N-（全氟辛基磺酰基）硫代磷酰胺催化的高度非对映选择性和对映选择性 Mukaiyama 羟醛反应。催化剂磺酰基上的全氟辛基取代基在立体选择中起重要作用。该催化剂还允许不对称的 Hosomi-Sakurai 烯丙基化，由于烯丙基硅烷的低反应性，这一直是相当具有挑战性的。(29)Si 和 (31)P NMR 监测揭示了硫代磷酰胺催化剂的特征，即使在存在过量甲硅烷基亲核试剂的情况下也能作为强布朗斯台德酸，这在其他相关的磷酸类似物中是找不到的。