2-<3'-(trifluoromethyl)phenyl>-2-adamantanol | 76481-48-6

• 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-<3'-(trifluoromethyl)phenyl>-2-adamantanol
• 英文别名: 2-(3-Trifluoromethylphenyl)-2-hydroxyadamantane；2-[3-(Trifluoromethyl)phenyl]adamantan-2-ol
• CAS: 76481-48-6
• 化学式: C₁₇H₁₉F₃O
• 分子量: 296.332
• InChiKey: FNYFQDGYCBASDW-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±37.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<3'-(trifluoromethyl)phenyl>-2-adamantanol 在 氯化亚砜 作用下， 以74%的产率得到2-chloro-2-<3'-(trifluoromethyl)phenyl>adamantane
  参考文献：
  名称：

  Solvolysis of 2-aryl-2-chloroadamantanes. A new Y scale for benzylic chlorides

  摘要：

  A series of 2-aryl-2-chloroadamantanes 2, Ar = 4'-methylphenyl, 4'-fluorophenyl, phenyl, 3'-chlorophenyl, 3'-(trifluoromethyl)phenyl, and 4'-(trifluoromethyl)phenyl, were prepared, and the solvolytic rate constants in 23 solvents were measured. Significant deviation from linear log k - Y(Cl) plots (m = 1.002, R = 0.959) was observed, and some orders of reactivities, e.g., k(100M) > k(90E) > k(80A), were in the reverse order of Swain's solvent parameter B. Different extent of solvation to the cationic transition state was then likely to play an important role. Excellent linear correlations between the logarithms of the ks for any pair in 2a-2f were realized, and the best one was that with respect to 2d. A new Y scale, Y(BnCl), for the correlation of solvolytic reactivities of benzylic chlorides based on k(2d) was established accordingly. The observation of decreasing m values with increasing electron-attracting ability of the substituent on the aryl ring of 2 also suggested the importance of charge delocalizations.

  DOI：

  10.1021/jo00009a018
• 作为产物：
  描述：

  2-chloro-2-<3'-(trifluoromethyl)phenyl>adamantane 以 乙醇 为溶剂， 生成 2-<3'-(trifluoromethyl)phenyl>-2-adamantanol
  参考文献：
  名称：

  Solvolysis of 2-aryl-2-chloroadamantanes. A new Y scale for benzylic chlorides

  摘要：

  A series of 2-aryl-2-chloroadamantanes 2, Ar = 4'-methylphenyl, 4'-fluorophenyl, phenyl, 3'-chlorophenyl, 3'-(trifluoromethyl)phenyl, and 4'-(trifluoromethyl)phenyl, were prepared, and the solvolytic rate constants in 23 solvents were measured. Significant deviation from linear log k - Y(Cl) plots (m = 1.002, R = 0.959) was observed, and some orders of reactivities, e.g., k(100M) > k(90E) > k(80A), were in the reverse order of Swain's solvent parameter B. Different extent of solvation to the cationic transition state was then likely to play an important role. Excellent linear correlations between the logarithms of the ks for any pair in 2a-2f were realized, and the best one was that with respect to 2d. A new Y scale, Y(BnCl), for the correlation of solvolytic reactivities of benzylic chlorides based on k(2d) was established accordingly. The observation of decreasing m values with increasing electron-attracting ability of the substituent on the aryl ring of 2 also suggested the importance of charge delocalizations.

  DOI：

  10.1021/jo00009a018

文献信息

• KOVALEV, VLADIMIR V.;ROZOV, ANDREY K.;SHOKOVA, ELVIRA A., SYNLETT.,(1990) N2, C. 739-740
  作者：KOVALEV, VLADIMIR V.、ROZOV, ANDREY K.、SHOKOVA, ELVIRA A.

  DOI：——

  日期：——
• [EN] 2-ADAMANTYLALKYLAMINES AND THEIR USE IN THE TREATMENT OF CONDITIONS GENERALLY ASSOCIATED WITH ABNORMALITIES IN GLUTAMATERGIC TRANSMISSION<br/>[FR] 2-ADAMANTYLALKYLAMINES ET LEUR UTILISATION DANS LE TRAITEMENT DE TROUBLES GENERALEMENT ASSOCIES A DES ANOMALIES DE LA TRANSMISSION GLUTAMATERGIQUE
  申请人：VERNALIS RES LTD

  公开号：WO2003064372A1

  公开（公告）日：2003-08-07

  The use of a compound of formula (1) wherein X is oxygen or (CR11R12)n; n is 0 or 1; R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently selected from hydrogen, alkyl, aryl and non-aromatic heterocyclic groups, or each of one or more pair(s) thereof may together form a 3, 4, 5, 6, 7 or 8-membered ring containing 0, 1 or 2 heteroatom(s); R9 is selected from alkyl, aryl and non-aromatic heterocyclic groups; and R10 is selected from hydrogen, halogen, alkyl, aryl and non-aromatic heterocyclic groups; and pharmaceutically acceptable salts and prodrugs thereof, in therapy and the manufacture of amedicament for use in the treatment of a condition generally associated with abnormalities in glutamatergic transmission, particularly Alzheimer's disease, ischaemic stroke, haemorrhagic stroke, epilepsy, multiple sclerosis, pain, drug-induced optic neuritis, myelopathy, glaucoma, peripheral neuropathy, ischaemic retinopathy, traumatic brain or spinal injury, Parkinson's Disease and Huntington's Disease; and novel compounds of formula (1) per se.