2-[p-(trifluoromethyl)phenyl]-2-adamantanol | 76481-50-0

• 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-[p-(trifluoromethyl)phenyl]-2-adamantanol
• 英文别名: 2-<4'-(trifluoromethyl)phenyl>-2-adamantanol；2-(4-trifluoromethylphenyl)-2-adamantanol；2-[4-(Trifluoromethyl)phenyl]adamantan-2-ol
• CAS: 76481-50-0
• 化学式: C₁₇H₁₉F₃O
• 分子量: 296.332
• InChiKey: ZFSWHZIAPGBMEI-UHFFFAOYSA-N

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-[p-(trifluoromethyl)phenyl]-2-adamantanol 在 氯化亚砜 作用下， 以73%的产率得到2-chloro-2-<4'-(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-<4'-(trifluoromethyl)phenyl>adamantane 以 乙醇 为溶剂， 生成 2-[p-(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

• 2-adamantanemethanamine compounds for treating abnormalities in glutamatergic transmission
  申请人：Vernalis Research Limited

  公开号：US06531511B1

  公开（公告）日：2003-03-11

  The use of a compound of formula (1), as disclosed in the specification, wherein R1, R2, R3, R4, R5 and R6 are independently selected from hydrogen, alkyl and aryl, or pharmaceutically acceptable salts thereof, with the proviso that wherein R1 to R4 and R6 are hydrogen, R5 is not selected from CH2CH2NHSO2CH3, CH2CH2NHSO2CF3 and methyl substituted by SO2NH2, SO3H, PO3H2, CONHOH or a heterocyclic group selected from formulae (a), (b), (c), (d) and (e) in the manufacture of a medicament for use in the treatment of a condition generally associated with abnormalities in glutamatergic transmission.

  在说明书中披露的公式（1）化合物的使用，其中R1、R2、R3、R4、R5和R6可独立选择为氢、烷基和芳基，或其药用盐，但其中R1至R4和R6为氢时，R5不可选择自CH2CH2NHSO2CH3、CH2CH2NHSO2CF3和甲基被SO2NH2、SO3H、PO3H2、CONHOH或从公式（a）、（b）、（c）、（d）和（e）中选择的杂环基团，用于制造用于治疗通常与谷氨酸能传递异常相关的病况的药物。
• Generation and Reactivity of 2-Substituted Adamantenes
  作者：Takao Okazaki、Kazuhiko Tokunaga、Toshikazu Kitagawa、Ken’ichi Takeuchi

  DOI：10.1246/bcsj.72.549

  日期：1999.3

  The title bridgehead olefins, generated by the dehalogenation of 1,2-dihalo-2-R-adamantanes (R = Me, Et, Ph, p-CF3C6H4) with excess t-BuLi, yielded 2-t-butyl-2-R-adamantanes (15), 1-t-butyl-2-R-adamantanes (16), and dimeric products. The ratios of the yields (%) of 16 to 15 were 20 : 3 (R = Me), 32 :< 1 (R = Et), 4 : 60 (R = Ph), and 5 : 57 (R = p-CF3C6H4). 2-Alkyladamantenes predominantly yielded

  标题桥头烯烃由 1,2-二卤-2-R-金刚烷（R = Me、Et、Ph、p-CF3C6H4）与过量的 t-BuLi 脱卤生成，得到 2-t-丁基-2-R -金刚烷 (15)、1-叔丁基-2-R-金刚烷 (16) 和二聚产物。16 比 15 的产率 (%) 比为 20:3 (R = Me)、32:< 1 (R = Et)、4: 60 (R = Ph) 和 5: 57 (R = p- CF3C6H4)。2-烷基金刚烷主要产生在 C(1) 处叔丁基化的产物，而 2-芳基金刚烷主要产生在 C(2) 处叔丁基化的产物。随着 C(2) 位置取代基的体积增大，二聚体的总产率下降。2-甲基金刚烷的二聚化得到头对头二聚体，1-(2-甲基-1-金刚烷基)-2-亚甲基金刚烷，以及头对尾二聚体，1-(2-甲基-2 -金刚烷基)-2-亚甲基金刚烷。两个2-苯基金刚烷分子之间的[4+2]环加成，其中苯基作为二烯的一部
• LIN, M. -H.;SILVER, J. E.;LE, NOBLE W. J., J. ORG. CHEM., 53,(1988) N 21, C. 5155-5158
  作者：LIN, M. -H.、SILVER, J. E.、LE, NOBLE W. J.

  DOI：——

  日期：——
• 2-ADAMANTANEMETHANAMINE COMPOUNDS FOR TREATING ABNORMALITIES IN GLUTAMATERGIC TRANSMISSION
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1143964A1

  公开（公告）日：2001-10-17
• US6531511B1
  申请人：——

  公开号：US6531511B1

  公开（公告）日：2003-03-11