[(1R,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.32
• InChiKey: IAXXETNIOYFMLW-WDMOLILDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

小量的甲基丙烯酸甲酯可以通过皂化作用轻易地代谢成醇和甲基丙烯酸。后者可以形成一个乙酰辅酶A衍生物，然后进入正常的脂质代谢。/甲基丙烯酸甲酯/

Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme A derivative, which then enters the normal lipid metabolism. /Methacrylates/

来源:Hazardous Substances Data Bank (HSDB)

代谢

丙烯酸酯和甲基丙烯酸酯主要通过迈克尔加成反应与谷胱甘肽结合或通过谷胱甘肽-S-转移酶进行解毒。它们还可能通过羧酸酯酶进行水解。较低分子量的酯类被迅速代谢和消除，因此不太可能引起累积毒性。/丙烯酸酯和甲基丙烯酸酯/

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity. /Acrylates andMethacrylates/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

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……。预见并处理癫痫发作……。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、有强烈的干呕反射且不流口水，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……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

Basic treatment: Establish a patent airway. 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 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于无意识、严重肺水肿或呼吸停止的患者，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。监测心率和必要时治疗心律失常。 ... 开始静脉输液，使用D5W/SRP：“保持开放”，最低流量/。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。考虑使用药物治疗肺水肿。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。用地西泮（安定）治疗癫痫。使用丙美卡因氢氯化物协助眼部冲洗。/毒药A和B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as 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. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

实验室动物：发育或生殖毒性/使用大鼠的动物研究显示，一些丙烯酸酯和甲基丙烯酸酯具有胚胎毒性。然而，动物研究中使用的单体剂量远高于工人可能接触到的浓度。/丙烯酸酯和甲基丙烯酸酯/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Animal studies using rats revealed that some acrylates and methacrylates are embryotoxic. The doses of monomers used in the animal studies, however, were much higher than concentrations likely encountered by workers. /Acrylates and Methacrylates/

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 [(1R,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate 在 N-甲基二环己基胺 、 4DPAIPN 作用下， 以 二甲基亚砜 为溶剂， 以65 %的产率得到2-methyl-3-oxo-3-(((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)oxy)propanoic acid
  参考文献：
  名称：

  活化烯烃与二氧化碳的解构羧化

  摘要：

  首次报道了一种用于烯烃与CO 2解构羧化的新型无金属光化学方法。该策略的威力在生物活性分子衍生物的后期羧化和丙酸酯非甾体抗炎药的合成中得到了证明。

  DOI：

  10.1002/anie.202313030

文献信息

• Deconstructive Carboxylation of Activated Alkenes with Carbon Dioxide
  作者：Pan‐Feng Yuan、Zhao Yang、Shan‐Shan Zhang、Can‐Ming Zhu、Xiu‐Long Yang、Qing‐Yuan Meng

  DOI：10.1002/anie.202313030

  日期：2024.1.25

  A novel metal-free photochemical method for the deconstructive carboxylation of alkenes with CO2 is reported for the first time. The power of this strategy is demonstrated for the late-stage carboxylation of bioactive molecule derivatives and the synthesis of propionate nonsteroidal anti-inflammatory drugs.

  首次报道了一种用于烯烃与CO 2解构羧化的新型无金属光化学方法。该策略的威力在生物活性分子衍生物的后期羧化和丙酸酯非甾体抗炎药的合成中得到了证明。