2-methyl-4-t-butylbenzyl alcohol | 129716-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-4-t-butylbenzyl alcohol
• 英文别名: 4-(1,1-Dimethylethyl)-2-methylbenzenemethanol；(4-tert-butyl-2-methylphenyl)methanol
• CAS: 129716-12-7
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: OXNTUXHFXUPSCC-UHFFFAOYSA-N

物化性质

• 沸点：
  232.6±8.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-4-t-butylbenzyl alcohol 在 氯化亚砜 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 2.0h， 生成 4-t-Butyl-2-methylphenylacetonitrile
  参考文献：
  名称：

  Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

  摘要：

  Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT1D (i.e., human 5-HT1D alpha) receptors, this modification reduced h5-HT1B (i.e., human 5-HT1D beta) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT1B binding than h5-HT1D binding.With the appropriate structural modifications, several compounds were identified that display 20- to >100-fold selectivity for h5-HT1D versus h5-HT1B receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT1D agonists are currently being explored for their antimigraine action and that activation of h5-HT1B receptors might be associated with cardiovascular side effects, h5-HT1D-selective agents may offer a new lead for the development of therapeutically efficacious agents.

  DOI：

  10.1021/jm970513p
• 作为产物：
  描述：

  4-叔丁基-2-甲基苯甲酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到2-methyl-4-t-butylbenzyl alcohol
  参考文献：
  名称：

  Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

  摘要：

  Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT1D (i.e., human 5-HT1D alpha) receptors, this modification reduced h5-HT1B (i.e., human 5-HT1D beta) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT1B binding than h5-HT1D binding.With the appropriate structural modifications, several compounds were identified that display 20- to >100-fold selectivity for h5-HT1D versus h5-HT1B receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT1D agonists are currently being explored for their antimigraine action and that activation of h5-HT1B receptors might be associated with cardiovascular side effects, h5-HT1D-selective agents may offer a new lead for the development of therapeutically efficacious agents.

  DOI：

  10.1021/jm970513p

文献信息

• Selectivity and mechanism in the side-chain halogenation of methylbenzenes promoted photochemically and by metal complexes in the presence of halide ions
  作者：Enrico Baciocchi、Manuela Crescenzi

  DOI：10.1016/s0040-4020(01)89841-0

  日期：——

  selective than bromination. Selectivity of CAN/Cl- is very similar to that of Cl2/hν, whereas significant differences are observed with cobalt(III) acetate/Cl-. Probably Cl· and a cobalt(III) chloride complex are the reacting species in CAN/Cl- and cobalt(III) acetate/Cl-, respectively.

  在AcOH中，通过测量4-叔丁基-和4-氯-1,2-二甲基苯（1和2，分别地）与能：Br 2 /hν，CAN /溴-，CAN =硝酸铈（IV）铵，钴（III）乙酸甲酯/溴-，S 2 ö 8 - /溴-，N-溴琥珀酰亚胺（在四氯化碳4）， CL 2 /hν，CAN /氯- ，钴（III）乙酸乙酯/氯-。在溴化反应中，选择性与反应条件无关，因此表明在所有溴化体系中，Br·是实际的反应物种。非常令人惊讶的是，以1为底物，Cl 2 /hν比Br 2 /hν具有更高的选择性。对于2，这两个系统显示出相似的选择性。已经提出，在AcOH中，用于光氯化的过渡态具有电子转移特性，该电子转移特性随着底物变得更富电子而增加。取代的甲苯的相对反应性数据支持在AcOH中进行光氯化的“可变”过渡态的想法，该数据表明，随着取代基变得更多的电子供体，对速率的影响也随之增加。自在CCl中以来，AcOH在这方面必须起重要作用
• Hydrogen atom transfer vs. electron transfer in iron(III) porphyrin catalysed benzylic oxidations
  作者：Enrico Baciocchi、Manuela Crescenzi、Osvaldo Lanzalunga

  DOI：10.1039/c39900000687

  日期：——

  The scope of hydrogen atom transfer and electron transfer mechanisms has been established for the benzylic oxidations of alkylaromatic compounds and benzyltrimethylsilanes induced by an iron(III) porphyrin complex.

  已经建立了由铁（III）卟啉配合物诱导的烷基芳族化合物和苄基三甲基硅烷的苄基氧化的氢原子转移和电子转移机理的范围。
• [EN] IMIDAZOLES WITH SEROTONIN RECEPTOR BINDING ACTIVITY<br/>[FR] IMIDAZOLES A ACTIVITE DE FIXATION DU RECEPTEUR DE LA SEROTONINE
  申请人：ALLELIX BIOPHARMACEUTICALS INC.

  公开号：WO1998012183A1

  公开（公告）日：1998-03-26

  (EN) This invention relates to compounds having serotonin receptor binding activity, to pharmaceutical compositions containing them and to their medical use, particularly in the treatment of CNS conditions. Described herein are compounds which have general formula (I), wherein R1 is selected from H, C1-6alkyl and benzyl; R2 is selected from H and C1-6alkyl; R3 is selected from H and C1-6alkyl; R4 is selected from C1-6alkyl and halo; R5 is selected from H and OH; and salts, hydrates and solvates thereof. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of subtypes of the serotonin receptor is implicated, such as migraine.(FR) L'invention porte sur des composés présentant une activité de fixation du récepteur de la sérotonine, sur des préparations pharmaceutiques les contenant et sur leurs utilisations médicales notamment pour le traitement des troubles du SNC, ainsi que sur leurs sels, hydrates et solvates. Lesdits composés répondent à la formule générale (I) dans laquelle: R1 est sélectionné parmi H, C1-6 alkyle et benzyle; R2 est sélectionné parmi H et C1-6 alkyle; R3 est sélectionné parmi H et C1-6 alkyle; R4 est sélectionné parmi C1-6 alkyle et halo; R5 est sélectionné parmi H et OH. L'invention porte également sur l'utilisation de ces composés comme produits pharmaceutiques pour traiter les cas où la stimulation des sous-types du récepteur de la sérotonine est en cause, tels que la migraine.

  本发明涉及具有5-羟色胺受体结合活性的化合物，包含它们的药物组成物以及它们在治疗中枢神经系统疾病方面的医学用途。本文描述了通式（I）的化合物，其中R1选自H、C1-6烷基和苄基；R2选自H和C1-6烷基；R3选自H和C1-6烷基；R4选自C1-6烷基和卤素；R5选自H和OH；以及它们的盐、水合物和溶剂化物。还描述了将这些化合物用作药物，以治疗与5-羟色胺受体亚型刺激有关的症状，例如偏头痛。
• BACIOCCHI, ENRICO;CRESCENZI, MANUELA;LANZALUNGA, OSVALDO, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 687-688
  作者：BACIOCCHI, ENRICO、CRESCENZI, MANUELA、LANZALUNGA, OSVALDO

  DOI：——

  日期：——
• AMODEO, RACHELE;BACIOCCHI, ENRICO;CRESCENZI, MANUELA;LANZALUNGA, OSVALDO, TETRAHEDRON LETT., 31,(1990) N4, C. 3477-3480
  作者：AMODEO, RACHELE、BACIOCCHI, ENRICO、CRESCENZI, MANUELA、LANZALUNGA, OSVALDO

  DOI：——

  日期：——