3,4-Dimethyl-2-phenylpentan-2-ol | 484001-23-2

• 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: 3,4-Dimethyl-2-phenylpentan-2-ol
• 英文别名: 3,4-dimethyl-2-phenylpentan-2-ol
• CAS: 484001-23-2
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: XHBVZPCAVSCBJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  3,4-Dimethyl-2-phenylpentan-2-ol 在 氘代硫酸 作用下， 以 重水 为溶剂， 反应 0.17h， 以51%的产率得到trans-2,3-Dihydro-1,1,2,3-tetramethyl-1H-inden
  参考文献：
  名称：

  Über Umlagerungen bei der Cyclialkylierung von Arylpentanolen zu 2,3-Dihydro-1H-inden-Derivaten, 5. Mitteilung

  摘要：

  The mechanism proposed in [1] to explain the surprising result of the cyclialkylation of 4-(2-chlorophenyl)-2,4-dimethylpentan-2-ol (3, R = Me), which gives not only the 'normal' product, i.e., the 4-chloro-2,3-dihydro-1,1,3,3-tetramethyl- (4), but also the isomer trans-4-chloro-2,3-dihydro-1,1,2,3-tetramethyl-1H-inden (5), could be differentiated in two sections (cf. Scheme 2): the first from 3 to the intermediary ion IIareversible arrowIIb, and the second from the latter ions to the final product 5. For the first section, a sufficiently satisfactory explanation has been given in [1]; the second section has received important support from the mechanisms of the cyclialkylation of 2,4-dimethyl-2-phenylpentan-3-ol (6), the precursor of II'a, the ion IIa without the o-Cl substituent (cf. Schemes 2, 3 and 5 and [4]). The present communication gives an explanation of the influence of the o-Cl substituent: a mechanism is proposed for the very complex cyclialkylation of 2-(2-chlorophenyl)-2,4-dimethylpentan-3-ol (11; cf Scheme 9). Both mechanism may be considered as definitive. It is very surprising that, by the cyclialkylation of the compounds 1, 3, 8, 11, 15, and 17, only compound 1 gives the 'normal' product; the cyclialkylation of all other phenylpentanols follows complex pathways including Et, i-Pr, and Ph migrations, which could not be expected. In addition, it has been established that the transformation of 21 to 22 (cf Scheme 12) and that of 23 to 24 (cf Scheme 13) occur through two consecutive 1,2- and not through a single 1,3-hydride migration or through an elimination-addition process (cf Scheme 13). It can be assumed that the transformation of ion IV (the 2-(2-chlorophenyl)-3,4-dimethylpent-2-ylium ion) to the ion V (the 4-(2-chlorophenyl)-3,4-dimethylpent-2-ylium ion (both shown in Scheme 9 as D-isomers) occurs through the same pathway.

  DOI：

  10.1002/1522-2675(200207)85:7<2089::aid-hlca2089>3.0.co;2-0
• 作为产物：
  描述：

  2-isopropyl-2-methyl-3-oxobuttersaeure-aethylester 在 氢溴酸 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 63.0h， 生成 3,4-Dimethyl-2-phenylpentan-2-ol
  参考文献：
  名称：

  Über Umlagerungen bei der Cyclialkylierung von Arylpentanolen zu 2,3-Dihydro-1H-inden-Derivaten, 5. Mitteilung

  摘要：

  The mechanism proposed in [1] to explain the surprising result of the cyclialkylation of 4-(2-chlorophenyl)-2,4-dimethylpentan-2-ol (3, R = Me), which gives not only the 'normal' product, i.e., the 4-chloro-2,3-dihydro-1,1,3,3-tetramethyl- (4), but also the isomer trans-4-chloro-2,3-dihydro-1,1,2,3-tetramethyl-1H-inden (5), could be differentiated in two sections (cf. Scheme 2): the first from 3 to the intermediary ion IIareversible arrowIIb, and the second from the latter ions to the final product 5. For the first section, a sufficiently satisfactory explanation has been given in [1]; the second section has received important support from the mechanisms of the cyclialkylation of 2,4-dimethyl-2-phenylpentan-3-ol (6), the precursor of II'a, the ion IIa without the o-Cl substituent (cf. Schemes 2, 3 and 5 and [4]). The present communication gives an explanation of the influence of the o-Cl substituent: a mechanism is proposed for the very complex cyclialkylation of 2-(2-chlorophenyl)-2,4-dimethylpentan-3-ol (11; cf Scheme 9). Both mechanism may be considered as definitive. It is very surprising that, by the cyclialkylation of the compounds 1, 3, 8, 11, 15, and 17, only compound 1 gives the 'normal' product; the cyclialkylation of all other phenylpentanols follows complex pathways including Et, i-Pr, and Ph migrations, which could not be expected. In addition, it has been established that the transformation of 21 to 22 (cf Scheme 12) and that of 23 to 24 (cf Scheme 13) occur through two consecutive 1,2- and not through a single 1,3-hydride migration or through an elimination-addition process (cf Scheme 13). It can be assumed that the transformation of ion IV (the 2-(2-chlorophenyl)-3,4-dimethylpent-2-ylium ion) to the ion V (the 4-(2-chlorophenyl)-3,4-dimethylpent-2-ylium ion (both shown in Scheme 9 as D-isomers) occurs through the same pathway.

  DOI：

  10.1002/1522-2675(200207)85:7<2089::aid-hlca2089>3.0.co;2-0

文献信息

• BENZOIMIDAZOL-1,2-YL AMIDES AS Kv7 CHANNEL ACTIVATORS
  申请人：Knopp Biosciences LLC

  公开号：US20160075663A1

  公开（公告）日：2016-03-17

  Optionally substituted benzoimidazol-1,2-yl amides, such as compounds of Formula 1 or Formula 2, can be used to treat disorders associated with a Kv7 potassium channel activator. Compositions, medicaments, and dosage forms related to the treatment are also disclosed herein.

  可选择替代的苯并咪唑-1,2-基酰胺，如式1或式2的化合物，可用于治疗与Kv7钾通道激活剂相关的疾病。本文还公开了与治疗相关的组合物、药物和剂型。
• BENZOIMIDAZOL-1,2-YL AMIDES AS KV7 CHANNEL ACTIVATORS
  申请人：Knopp Biosciences LLC

  公开号：EP3572405A1

  公开（公告）日：2019-11-27

  Optionally substituted benzoimidazol-1,2-yl amides (formula) can be used to treat disorders associated with a Kv7 potassium channel activator. Compositions, medicaments, and dosage forms related to the treatment are also disclosed herein.

  任选取代的苯并咪唑-1,2-基酰胺（式）可用于治疗与 Kv7 钾通道激活剂相关的疾病。本文还公开了与治疗相关的组合物、药物和剂型。
• KV7 CHANNEL ACTIVATORS COMPOSITIONS AND METHODS OF USE
  申请人：Knopp Biosciences LLC

  公开号：US20210130299A1

  公开（公告）日：2021-05-06

  Provided herein are optionally substituted benzoimidazol-1,2-yl amides, pharmaceutical compositions comprising a therapeutically effective amount of such compounds and a pharmaceutically acceptable excipient, and methods of treating Kv7 associated diseases, such as, epilepsy, amyotrophic lateral sclerosis, various types of pain, hyperexcitability, a dyskinesia, dystonia, mania and tinnitus with such compounds and pharmaceutical compositions.
• US9481653B2
  申请人：——

  公开号：US9481653B2

  公开（公告）日：2016-11-01
• US9914708B2
  申请人：——

  公开号：US9914708B2

  公开（公告）日：2018-03-13