1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine | 143919-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine
• 英文别名: (-)-1,3-Dimethyl-1,2,3,6-tetrahydro-4-[3-(1-methylethoxy)phenyl]pyridine；(3S)-1,3-dimethyl-4-(3-propan-2-yloxyphenyl)-3,6-dihydro-2H-pyridine；1,3-dimethyl-4-(3-propan-2-yloxyphenyl)-3,6-dihydro-2H-pyridine
• CAS: 143919-46-4
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: JCOCMGVCOFDDLL-UHFFFAOYSA-N

物化性质

• 沸点：
  349.6±42.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 6.5h， 生成 phenyl 4-(benzyloxymethyl)-4-(3-isopropoxyphenyl)-3-methylpiperidine-1-carboxylate
  参考文献：
  名称：

  （3 R *，4 R *）-和（3 R *，4 S *）-4-芳基-3-甲基-4-哌啶甲醇和氟类似物的非对映选择性合成

  摘要：

  由1，3-二甲基-4-哌啶酮实现了两个简明且高产的4-芳基-3-甲基-4-哌啶甲醇的非对映选择性合成。控制C3–C4相对立体化学的关键反应是由4-芳基-3-甲基-1,2,3,6-四氢吡啶生成的金属烯胺的烷氧基甲基化，提供了（3 R *，4 S *）形式并用去质子化的3-甲基-4-哌啶腈进行氟芳烃的亲核取代，得到（3R *，4 R *）-异构体。随后通过使用DAST对哌啶甲醇进行氟化来获得相应的氟甲基类似物。

  DOI：

  10.1021/jo302303h
• 作为产物：
  描述：

  cis-(-)-carbonic acid ethyl 1,3-dimethyl-4-[3-(l-methylethoxy)phenyl]-4-piperidinyl ester 在 sodium hydroxide 作用下， 以 萘烷 为溶剂， 生成 1,2,3,4-tetrahydro-1,3-dimethyl-4-<3-(1-methylethoxy)phenyl>pyridine
  参考文献：
  名称：

  Preparation of substituted tetrahydropyridines

  摘要：

  提供了一种制备特定的1,3,4,4-四取代-1,2,3,4-四氢吡啶以及特定的4-碳酸酯-1,3,4-三取代哌啶的方法。

  公开号：

  US05136040A1

文献信息

• [EN] 2-AZABICYCLO[3.3.1]NONANE DERIVATIVES AS OPIOID RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE 2-AZABICYCLO[3.3.1]NONANE UTILISES COMME ANTAGONISTES DES RECEPTEURS OPIOIDES
  申请人：PFIZER PROD INC

  公开号：WO2004089909A1

  公开（公告）日：2004-10-21

  The subject invention relates to 2-azabicyclo[3.3.1 ]nonane derivatives, pharmaceutical compositions comprising such derivatives and methods of using such derivatives to treat disease states, disorders and conditions mediated by opioid receptors. The subject invention also particularly relates to using such derivatives to treat certain disorders and conditions, for example irritable bowel syndrome, drug addiction, including alcohol addiction, depression, anxiety, schizophrenia and eating disorders, among others, as are more fully described herein. Formula (I):

  本发明涉及2-azabicyclo [3.3.1]非缩酮衍生物，包括这种衍生物的制药组合物以及使用这种衍生物治疗由阿片受体介导的疾病状态，紊乱和病况的方法。本发明特别涉及使用这种衍生物治疗某些紊乱和病况，例如肠易激综合症，药物成瘾，包括酒精成瘾，抑郁症，焦虑症，精神分裂症和进食紊乱等，如本文所述。公式（I）：
• Kappa opioid receptor ligands
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：US20020143145A1

  公开（公告）日：2002-10-03

  Structurally novel kappa opioid receptor antagonists are provided and the use of these antagonists in treatment of disease states that are ameliorated by binding of the kappa opioid receptor such as heroin or cocaine addictions.

  提供了结构新颖的kappa阿片受体拮抗剂，并且这些拮抗剂的使用可以治疗与kappa阿片受体结合有关的疾病状态，例如海洛因或可卡因成瘾。
• Synthesis of <i>trans</i>-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine Opioid Antagonists:  Application of the <i>Cis</i>-Thermal Elimination of Carbonates to Alkaloid Synthesis
  作者：John A. Werner、Louis R. Cerbone、Scott A. Frank、Jeffrey A. Ward、Parviz Labib、Roger W. Tharp-Taylor、C. W. Ryan

  DOI：10.1021/jo951403y

  日期：1996.1.1

  Improved syntheses of two trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists from 1,3-dimethyl-4-piperidinone are described. The 1,3 dimethyl-4-arylpiperidinol 23 was selectively dehydrated in a two step process to the 1,3-dimethyl-4-aryl-1,2,3,6-tetrahydropyrodome 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190 degrees C. In the presence of a basic nitrogen, the success of the elimination was found to be critically dependent upon the nature of the carbonate alkyl group, with Et, i-Bu, and i-Pr being preferred (90% yield). Alkylation of the metalloenamine, formed by deprotonation of 26 with n-BuLi, proceeded regio- and stereospecifically to give the trans-3,4-dimethyl-4-aryl-1,2,3,4-tetrahydrpyridine 27, which was converted in three steps to the common intermediate, (3R,4R)-3,4-dimethyl-4-(3-hydroxyphenyl)-piperidine. LY255582, a centrally-active opioid antagonist, and LY246736-dihydrate, a peripherally-active opioid antagonist, were prepared from 1,3-dimethyl-4-piperidinone in 11.8% yield (8 steps) and 6.2% yield (12 steps), respectively.
• KAPPA OPIOID RECEPTOR LIGANDS
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：EP1363629B1

  公开（公告）日：2009-09-16
• OPIOID RECEPTOR AGONIST COMPOUNDS AND THEIR USE IN TREATMENT OF PAIN
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：EP1874310A2

  公开（公告）日：2008-01-09