2-((5-isopropyl-2-methylphenoxy)methyl)oxirane | 60217-55-2

• 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: 2-((5-isopropyl-2-methylphenoxy)methyl)oxirane
• 英文别名: 2-[(2-Methyl-5-propan-2-ylphenoxy)methyl]oxirane
• CAS: 60217-55-2
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: XUJQXXSPEVSZDT-UHFFFAOYSA-N

物化性质

• 沸点：
  157 °C(Press: 14.5 Torr)
• 密度：
  1.030±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((5-isopropyl-2-methylphenoxy)methyl)oxirane 在 硫脲 作用下， 以 甲醇 为溶剂， 以98 %的产率得到2-((5-isopropyl-2-methylphenoxy)methyl)thiirane
  参考文献：
  名称：

  作为代谢酶抑制剂的新型香芹酚基 2-氨基硫醇和磺酸衍生物的合成、表征和计算研究

  摘要：

  合成了八种新的 2-氨基硫醇 (69–96%) 和三种新的磺酸 (51–76%)，并通过 NMR 和 HRMS 谱进行了表征。本研究介绍了一系列新型香芹酚基 2-氨基硫醇和磺酸衍生物 ( 3a-f,4a-c ) 对人碳酸酐酶 I 和 II 同工酶 (hCA I 和 II)、乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶的抑制作用(BChE) 和 α-糖苷酶。K i值计算为：hCA I 为 12.52±3.61–335.65±60.56 nM，hCA II 为 12.20±3.59–389.69±119.41 nM，AChE 为 1.79±0.56–84.86±23.34 nM，AChE 为 6.57±2.54–88.05±21.05 nM BChE 和 14.63±4.76–116.39±33.70 nM α-葡萄糖苷酶。此外，还分别将基于香芹酚的新型 2-氨基硫醇 ( 3a-h ) 和磺酸衍生物

  DOI：

  10.1016/j.molstruc.2024.137516
• 作为产物：
  描述：

  香芹酚 、 环氧氯丙烷 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以95 %的产率得到2-((5-isopropyl-2-methylphenoxy)methyl)oxirane
  参考文献：
  名称：

  作为代谢酶抑制剂的新型香芹酚基 2-氨基硫醇和磺酸衍生物的合成、表征和计算研究

  摘要：

  合成了八种新的 2-氨基硫醇 (69–96%) 和三种新的磺酸 (51–76%)，并通过 NMR 和 HRMS 谱进行了表征。本研究介绍了一系列新型香芹酚基 2-氨基硫醇和磺酸衍生物 ( 3a-f,4a-c ) 对人碳酸酐酶 I 和 II 同工酶 (hCA I 和 II)、乙酰胆碱酯酶 (AChE)、丁酰胆碱酯酶的抑制作用(BChE) 和 α-糖苷酶。K i值计算为：hCA I 为 12.52±3.61–335.65±60.56 nM，hCA II 为 12.20±3.59–389.69±119.41 nM，AChE 为 1.79±0.56–84.86±23.34 nM，AChE 为 6.57±2.54–88.05±21.05 nM BChE 和 14.63±4.76–116.39±33.70 nM α-葡萄糖苷酶。此外，还分别将基于香芹酚的新型 2-氨基硫醇 ( 3a-h ) 和磺酸衍生物

  DOI：

  10.1016/j.molstruc.2024.137516

文献信息

• Copper‐Catalyzed Decarboxylative Alkylselenation of Propiolic Acids with Se Powder and Epoxides
  作者：Yujing Yao、Caihong Wang、Yunfei Ma、Jintao Zhang、Dong Sun、Luya Chen、Lehao Huang、Ge Wu

  DOI：10.1002/adsc.202001510

  日期：2021.3.29

  A copper‐catalyzed decarboxylative alkylselenation of propiolic acids with Se powder and epoxides leading to alkynyl selenides is developed. This protocol not only provides an approach to obtain alkynyl selenides with the formation of double C−Se bonds, but also expands the applicability of alkynyl carboxylic acid.

  开发了一种铜催化的丙酸与硒粉和环氧化合物的脱羧烷基硒化反应，形成炔基硒化物。该方案不仅提供了获得具有双C-Se键的炔基硒化物的方法，而且扩展了炔基羧酸的适用性。
• Marle, Journal of the Chemical Society, 1912, vol. 101, p. 309
  作者：Marle

  DOI：——

  日期：——
• Novel carvacrol based new oxypropanolamine derivatives: Design, synthesis, characterization, biological evaluation, and molecular docking studies
  作者：Arlinda Bytyqi-Damoni、Ali Kestane、Parham Taslimi、Burak Tuzun、Mustafa Zengin、Hayriye Genc Bilgicli、İlhami Gulcin

  DOI：10.1016/j.molstruc.2019.127297

  日期：2020.2

  Carvacrol, as a natural product used for many years in the treatment of various diseases, therefore it was chosen as the starting compound for this study. Novel carvacrol based new oxypropanolamine derivatives were synthesized and characterized by spectroscopic methods. All new compounds were tested as metabolic enzyme inhibitory agents. Their clinical usage of carvacrol has been established as diuretics, antiepileptics, and anti-glaucoma factors, in the management of gastric, duodenal ulcers, mountain sickness, osteoporosis, idiopathic intracranial hypertension, or neurological disorders. The in vitro anti-hyperglycemic screening results showed that the compound 3d exhibits the maximum inhibitory effect against alpha-glycosidase enzyme (IC50: 904.10 nM). In addition, the compounds 3d (IC50: 29.74 nM and 23.64 nM) and 3e (IC50: 31.28 nM and 26.11 nM) were found to have a significant response to inhibit carbonic anhydrase I, and II isoenzymes (hCA I and II), respectively. The novel carvacrol based oxypropanolamine compounds were effective inhibitors of the hCA I and II isozymes, and acetylcholinesterase with Ki values in the range of 27.18-44.84 nM for hCA I, 25.62-38.71 nM for hCA II, and 99.83-146.25 nM for AChE, respectively. (C) 2019 Elsevier B.V. All rights reserved.y
• Dwivedi; Shukla; Bhandari, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 2, p. 281 - 285
  作者：Dwivedi、Shukla、Bhandari、Setty、Kamboj、Khanna

  DOI：——

  日期：——
• Cu(II), Ni(II), Zn(II) and Fe(III) complexes containing a N2O2 donor ligand: Synthesis, characterization, DNA cleavage studies and crystal structure of [Cu(HL)Cl]
  作者：Rakesh S. Sancheti、Ratnamala S. Bendre、Anupa A. Kumbhar

  DOI：10.1016/j.poly.2011.06.032

  日期：2012.1

  A polydentate ligand, H2L ''[1-(5-isopropyl-2-methyl phenoxy)-3-(N-2-hydroxy benzyl-N-((pyridine-2yl)amino) propan-2-ol]'', containing a N2O2 donor moiety was synthesized by refluxing 2-((5-isopropyl-2-methylphenoxy)methyl)oxirane and HBPA (N-(2-hydroxybenzyI)-N-(2-Pyridylmethyl)amine). This synthesized ligand was used for the preparation of complexes with different metal ions, viz. [Cu(HL)Cl] (1), [Ni(HL)Cl] (2), [Zn(HL)Cl] (3) and [Fe(HL)Cl-2] (4). The ligand and metal complexes were characterized by H-1 NMR, mass, ESI-MS, elemental analysis, IR. UV-Vis and electron paramagnetic resonance (EPR) spectroscopy. The crystal structure for one of the complexes, [Cu(HL)Cl], was solved from the X-ray crystallography data. The structure of the complex, based on the trigonality index tau, suggests an intermediate geometry between square pyramidal (sp) and trigonal bipyramidal (tb). Both the ligand and the metal complexes show oxidative cleavage of plasmid DNA (pBR322) without addition of any exogenous agent, even at a concentration of 5 mu M. The binding constants for these compounds were found to be in the range 5.33-0.065 x 10(5) M-1. (C) 2011 Elsevier Ltd. All rights reserved.