5-chloro-2-methoxyphenyl acetate | 66037-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 5-chloro-2-methoxyphenyl acetate
• 英文别名: Phenol, 5-chloro-2-methoxy, acetate；(5-chloro-2-methoxyphenyl) acetate
• CAS: 66037-03-4
• 化学式: C₉H₉ClO₃
• 分子量: 200.622
• InChiKey: GXDSCZFYWIDHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-methoxyphenyl acetate 、 烯丙基三甲基硅烷 在 caesium carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 18.0h， 以57%的产率得到2-甲氧基-5-丙-2-烯基苯酚
  参考文献：
  名称：

  通过无金属的光烯丙基化程序快速合成Piper属的生物活性烯丙基苯酚成分。

  摘要：

  存在于Piper属的几种植物中的九种生物活性烯丙基苯酚（茴香醚）衍生物（例如丁子香酚，丁香酚和天麻素）已通过芳基阳离子中间体以中等至高收率合成。这种快速的无金属程序涉及在烯丙基三甲基硅烷的存在下，在极性溶剂（MeCN或更好的TFE或乙腈水溶液）中辐照相应的氯酚或氯苯甲醚。虽然产率较低，但也从相应的氟衍生物和重氮盐开始合成了Estragole。

  DOI：

  10.1039/b506735a
• 作为产物：
  描述：

  邻甲氧基苯乙酸酯 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 336.0h， 以76%的产率得到5-chloro-2-methoxyphenyl acetate
  参考文献：
  名称：

  通过无金属的光烯丙基化程序快速合成Piper属的生物活性烯丙基苯酚成分。

  摘要：

  存在于Piper属的几种植物中的九种生物活性烯丙基苯酚（茴香醚）衍生物（例如丁子香酚，丁香酚和天麻素）已通过芳基阳离子中间体以中等至高收率合成。这种快速的无金属程序涉及在烯丙基三甲基硅烷的存在下，在极性溶剂（MeCN或更好的TFE或乙腈水溶液）中辐照相应的氯酚或氯苯甲醚。虽然产率较低，但也从相应的氟衍生物和重氮盐开始合成了Estragole。

  DOI：

  10.1039/b506735a

文献信息

• Direct Acetoxylation of Arenes
  作者：Thi Anh Hong Nguyen、Duen-Ren Hou

  DOI：10.1021/acs.orglett.1c02183

  日期：2021.11.5

  Acetoxylation of arenes is an important reaction and an unmet need in chemistry. We report a metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid, and acetic anhydride. Arenes (31 examples), with oxidation potentials (Eox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A

  芳烃的乙酰氧基化是一个重要的反应，也是化学中未满足的需求。我们报告了在三氟乙酸、乙酸和乙酸酐的无水环境下使用硝酸钠进行的无金属直接乙酰氧基化反应。芳烃（31 个实例）的氧化电位（E ox，单位为 V vs SCE）低于苯（2.48 V），以良好的产率和区域选择性被乙酰氧基化。提出了一种逐步的单电子转移机制。
• Drowsiness and Poor Feeding in a Breast-Fed Infant: Association with Nefazodone and its Metabolites
  作者：Patrick Yapp、Kenneth F Ilett、Judith H Kristensen、L Peter Hackett、Michael J Paech、Jonathon Rampono

  DOI：10.1345/aph.10120

  日期：2000.11

  To investigate whether adverse effects in a premature neonate could be attributed to nefazodone exposure via breast milk.

  The breast-fed white infant (female, 2.1 kg, 36 weeks corrected gestational age) of a 35-year-old woman (60 kg) taking nefazodone 300 mg/d was admitted to the hospital because she was drowsy, lethargic, unable to maintain normal body temperature, and was feeding poorly. A diagnosis of exposure to nefazodone via breast milk was considered only after other more likely diagnoses had been excluded. After breast feeding was discontinued, the infant's symptoms resolved slowly over a period of 72 hours. The maternal plasma and milk concentration—time profiles for nefazodone and its metabolites, triazoledione, HO-nefazodone, and m-chlorphenylpiperazine, were quantified by HPLC. The calculated infant dose for nefazodone and its active metabolites (as nefazodone equivalents) via the milk was only 0.45% of the weight-adjusted maternal nefazodone daily dose.

  Our data suggest a putative association between maternal nefazodone ingestion and adverse effects in a premature breast-fed neonate. The measured amount of drug exposure would normally be considered safe in a full-term infant. However, there was a temporal relationship between resolution of adverse effects in the infant and cessation of breastfeeding.

  This case highlights the importance of individualizing the risk—benefit analysis for exposure to antidepressants in breast milk, especially when dealing with premature neonates.

  探讨早产儿是否由于通过母乳摄入nefazodone而产生不良反应。

  一名35岁女性（60公斤）每日服用nefazodone 300毫克，其母乳喂养的白种女婴（体重2.1公斤，36周矫正孕龄）因昏昏欲睡、懒散、无法维持正常体温并且喂养困难而被送入医院。仅在排除了其他更可能的诊断后，才考虑通过母乳摄入nefazodone导致的症状。在停止母乳喂养后，婴儿的症状缓慢缓解，历时72小时。通过高效液相色谱法测定了母亲血浆和乳汁中nefazodone及其代谢物triazoledione、HO-nefazodone和m-chlorphenylpiperazine的浓度-时间曲线。根据体重调整的母亲nefazodone每日剂量计算，婴儿通过乳汁摄入的nefazodone及其活性代谢物（作为nefazodone当量）仅占母亲剂量的0.45％。

  我们的数据表明，母亲服用nefazodone与早产婴儿母乳喂养后出现的不良反应可能存在关联。在足月婴儿中，测量到的药物暴露量通常被认为是安全的。然而，婴儿不良反应的缓解与母乳喂养的停止存在时间上的关系。

  这个案例突出了在处理早产婴儿的抗抑郁药物母乳摄入风险-收益分析时个体化的重要性。

• <scp>Palladium‐catalyzed</scp> C <b></b> H acetoxylation of arenes using a pyrazolonaphthyridine ligand
  作者：Jisu Kim、Jung Min Joo

  DOI：10.1002/bkcs.12599

  日期：2022.10

  Herein, Pd-catalyzed CH acetoxylation reactions of arenes are developed using a pyrazolonaphthyridine ligand. In the presence of iodomesitylene diacetate as the oxidant, the electron-deficient ligand facilitates the CH activation of the electron-rich positions while preventing the formation of Pd black via bidentate binding. Although both acetic acid and hexafluoroisopropanol are employed for directing

  在此，使用吡唑并萘啶配体开发了 Pd 催化的芳烃 C  H 乙酰氧基化反应。在碘代三亚甲基二乙酸酯作为氧化剂存在的情况下，缺电子配体促进富电子位置的 CH 活化，同时通过双齿结合防止 Pd 黑的形成。尽管乙酸和六氟异丙醇都用于指导基团辅助的乙酰氧基化反应，但后者被证明对于芳烃与氮配体的非定向反应更有效。
• Characterization of high molecular mass fractions of receiving waters and sediments of a pulp mill by CuO-oxidation and HPLC
  作者：J. Hyötyläinen、J. Knuutinen、E. Vilén

  DOI：10.1016/0045-6535(94)00448-4

  日期：1995.3

  High molecular mass fractions were separated by ultrafiltration from water samples collected at four sampling stations downstream and one upstream of a kraft pulp mill. These fractions and three sediment samples containing high molecular mass organic compounds were degraded by alkaline cupric oxide oxidation. Lignin and humic compounds in fractions were characterized analyzing their oxidation products by reversed phase HPLC and photodiode array detection.
• Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure
  作者：Stefano Protti、Maurizio Fagnoni、Angelo Albini

  DOI：10.1039/b506735a

  日期：——

  synthesized in medium to high yield via aryl cation intermediates. This expeditious metal-free procedure involves the irradiation of the corresponding chlorophenols or chloroanisoles in a polar solvent (MeCN or, better, TFE or aqueous acetonitrile) in the presence of allyltrimethylsilane. Estragole has also been synthesized starting from the corresponding fluoroderivative and diazonium salt, though in a

  存在于Piper属的几种植物中的九种生物活性烯丙基苯酚（茴香醚）衍生物（例如丁子香酚，丁香酚和天麻素）已通过芳基阳离子中间体以中等至高收率合成。这种快速的无金属程序涉及在烯丙基三甲基硅烷的存在下，在极性溶剂（MeCN或更好的TFE或乙腈水溶液）中辐照相应的氯酚或氯苯甲醚。虽然产率较低，但也从相应的氟衍生物和重氮盐开始合成了Estragole。