tert-butyldimethyl[1-(3-chlorophenyl)prop-1-enyloxy]silane | 291275-45-1

• 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: tert-butyldimethyl[1-(3-chlorophenyl)prop-1-enyloxy]silane
• 英文别名: (Z)-tert-butyl-[1-(3-chlorophenyl)prop-1-enyloxy]dimethylsilane；[[(1Z)-1-(3-Chlorophenyl)-1-propenyl]oxy](1,1-dimethylethyl)dimethyl-silane; 1-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]benzene；tert-butyl-[(Z)-1-(3-chlorophenyl)prop-1-enoxy]-dimethylsilane
• CAS: 291275-45-1
• 化学式: C₁₅H₂₃ClOSi
• 分子量: 282.886
• InChiKey: FUWJCOIFTHDHNC-AUWJEWJLSA-N

物化性质

• 沸点：
  310.4±21.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮;二氯甲烷；乙酸乙酯;甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyldimethyl[1-(3-chlorophenyl)prop-1-enyloxy]silane 在 AD-mix-β 、 lutidine 、 水 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 生成 (2S,3S)-2-(3-氯苯基)-3,5,5-三甲基吗啉-2-醇
  参考文献：
  名称：

  Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

  摘要：

  A stereospecific method for the synthesis of enantiopure alpha -aminoketone from its corresponding alpha -hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupropion and its biologically active hydroxylated metabolite, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00349-9
• 作为产物：
  描述：

  3'-氯丙酮苯 生成 tert-butyldimethyl[1-(3-chlorophenyl)prop-1-enyloxy]silane
  参考文献：
  名称：

  [EN] BUPROPION METABOLITES AND METHODS OF THEIR SYNTHESIS AND USE
  [FR] METABOLITES DU BUPROPION ET LEURS PROCEDES DE SYNTHESE ET D'UTILISATION

  摘要：

  本发明公开了利用丁丙腈代谢物治疗神经元单胺再摄取抑制改善的疾病的方法和组合物。这些疾病包括但不限于性功能障碍、情感障碍、脑功能障碍、吸烟和失禁。本发明还公开了制备光学纯丁丙腈代谢物的方法。

  公开号：

  WO2001062257A2

文献信息

• Palladium-catalysed alkene chain-running isomerization
  作者：Andrew L. Kocen、Maurice Brookhart、Olafs Daugulis

  DOI：10.1039/c7cc04953f

  日期：——

  We report a method for palladium-catalysed chain-running isomerization of terminal and internal alkenes. Using an air-stable 2,9-dimethylphenanthroline-palladium catalyst in combination with NaBAr4 promoter, olefins are converted to the most stable double bond isomer at −30 to 20 °C. Silyl enol ethers are readily formed from silylated allylic alcohols. Fluorinated substituents are compatible with the

  我们报告了末端和内部烯烃的钯催化链运行异构化的方法。使用空气稳定的2,9-二甲基菲咯啉-钯催化剂与NaBAr 4助催化剂结合，可在-30至20°C的条件下将烯烃转化为最稳定的双键异构体。甲硅烷基烯醇醚易于由甲硅烷基化的烯丙醇形成。氟化取代基与反应条件相容，从而可以合成氟烯酸酯。可以以克为单位使用低至0.05％的催化剂负载量。
• HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE
  申请人：Research Triangle Institute

  公开号：US20130150357A1

  公开（公告）日：2013-06-13

  The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

  本发明提供了一种羟基丙酮类似物，能够抑制一个或多个单胺的再吸收和/或作为尼古丁乙酰胆碱受体的拮抗剂。这些化合物可以选择性地结合到一个或多个单胺转运体上，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体，和/或可以选择性地结合到一个或多个尼古丁乙酰胆碱受体亚型上。这些化合物可以用于治疗对单胺水平调节和/或尼古丁乙酰胆碱受体拮抗剂敏感的疾病，包括药物依赖、抑郁症和肥胖症。
• Hydroxybupropion analogues for treating drug dependence
  申请人：Research Triangle Institute

  公开号：US08906908B2

  公开（公告）日：2014-12-09

  The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

  该发明提供了羟基丁酮类似物，能够抑制一个或多个单胺的再摄取，并/或作为尼古丁乙酰胆碱受体的拮抗剂。这些化合物可以选择性地结合到一个或多个单胺转运体，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体，和/或可以选择性地结合到一个或多个尼古丁乙酰胆碱受体亚型。这些化合物可以用于治疗对单胺水平修饰和/或尼古丁乙酰胆碱受体拮抗剂有反应的疾病，包括药物依赖、抑郁症和肥胖症。
• [EN] 1 - PHENYLMORPHOLINE DERIVATIVES AS HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE<br/>[FR] ANALOGUES D'HYDROXYBUPROPION POUR LE TRAITEMENT DE LA PHARMACODÉPENDANCE
  申请人：RES TRIANGLE INST

  公开号：WO2011146821A3

  公开（公告）日：2012-01-12
• Synthesis and Characterization of in Vitro and in Vivo Profiles of Hydroxybupropion Analogues: Aids to Smoking Cessation
  作者：Ronald J. Lukas、Ana Z. Muresan、M. Imad Damaj、Bruce E. Blough、Xiaodong Huang、Hernán A. Navarro、S. Wayne Mascarella、J. Brek Eaton、Syndia K. Marxer-Miller、F. Ivy Carroll

  DOI：10.1021/jm1003232

  日期：2010.6.24

  To create potentially superior aids to smoking cessation and/or antidepressants and to elucidate bupropion's possible mechanisms of action(s), 23 analogues based on its active hydroxymetabolite (2S,35)-4a were synthesized and tested for their abilities to inhibit monoamine uptake and nAChR subtype activities in vitro and acute effects of nicotine in vivo. The 3',4'-dichlorophenyl [(+/-)-4n], naphthyl (4r), and 3-chlorophenyl or 3-propyl analogues 4s and 4t, respectively, had higher inhibitory potency and/or absolute selectivity than (2S,3S)-4a for inhibition of DA, NE, or 5HT uptake. The 3'-fluorophenyl, 3'-bromophenyl, and 4-biphenyl analogues 4c, 4d, and 4l, respectively, had higher potency for antagonism of alpha 4 beta 2-nAChR than (2S,3S)-4a. Several analogues also had higher potency than (2S,35)-4a as antagonists of nicotine-mediated antinociception in the tail-flick assay. The results suggest that compounds acting via some combination of DA, NE, or 5HT inhibition and/or antagonism of alpha 4 beta 2-nAChR can potentially be new pharmacotherapeutics for treatment of nicotine dependence.