(R)-2-hydroxy-1-(naphthalen-1-yl)propan-1-one | 1231951-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-hydroxy-1-(naphthalen-1-yl)propan-1-one
• 英文别名: (2R)-2-hydroxy-1-naphthalen-1-ylpropan-1-one
• CAS: 1231951-80-6
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: FWYAWAVMEZKFQD-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 (R)-2-hydroxy-1-(naphthalen-1-yl)propan-1-one 在 1,8-双二甲氨基萘 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Characterization of in Vitro and in Vivo Profiles of Hydroxybupropion Analogues: Aids to Smoking Cessation

  摘要：

  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.

  DOI：

  10.1021/jm1003232
• 作为产物：
  描述：

  (Z)-tert-butyldimethyl-(1-(naphthalen-1-yl)prop-1-enyloxy)silane 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以38%的产率得到(R)-2-hydroxy-1-(naphthalen-1-yl)propan-1-one
  参考文献：
  名称：

  Synthesis and Characterization of in Vitro and in Vivo Profiles of Hydroxybupropion Analogues: Aids to Smoking Cessation

  摘要：

  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.

  DOI：

  10.1021/jm1003232
• 作为试剂：
  描述：

  (Z)-tert-butyldimethyl-(1-(naphthalen-1-yl)prop-1-enyloxy)silane 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 甲基磺酰胺 在 (R)-2-hydroxy-1-(naphthalen-1-yl)propan-1-one 、 Disodium;sulfite 、 silica gel 作用下， 以 Water tert-butyl alcohol 为溶剂， 以1.15 g (38%) of the title product was isolated的产率得到(R)-2-hydroxy-1-(naphthalen-1-yl)propan-1-one
  参考文献：
  名称：

  HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE

  摘要：

  本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。这些化合物可用于治疗对单胺水平调节和/或尼古丁乙酰胆碱受体拮抗有反应的疾病，包括药物依赖、抑郁症和肥胖症。

  公开号：

  US20150141416A1

文献信息

• N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidant
  作者：Naoya Tanaka、Ryosuke Tsutsumi、Daisuke Uraguchi、Takashi Ooi

  DOI：10.1039/c7cc02502e

  日期：——

  A novel class of chiral N-sulfonyl oxaziridines is introduced for use as structurally modifiable chiral oxidants. These oxaziridines are readily prepared from N-sulfonyl α-imino esters in a highly enantioenriched form by oxidation with hydrogen peroxide using L-isoleucine-derived triaminoiminophosphorane as a catalyst. The distinct advantage of their structural modularity is demonstrated through the

  引入了一类新的手性N-磺酰基恶二氮杂烷用作结构上可修饰的手性氧化剂。这些恶唑烷很容易通过以L-异亮氨酸衍生的三氨基亚氨基膦烷为催化剂，用过氧化氢氧化，以高度对映体富集的形式由N-磺酰基α-亚氨基酯制备。通过鉴定最佳的恶唑烷，证明了其结构模块性的明显优势，所述最佳的恶唑烷在甲硅烷基烯醇醚与N-磺酰基烯丙基和均烯丙基胺的不对称氧化中表现出高反应活性和对映体特异性。
• 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。
• 1-PHENYLMORPHOLINE DERIVATIVES AS HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE
  申请人：Research Triangle Institute

  公开号：EP2571859B1

  公开（公告）日：2015-07-22
• US8906908B2
  申请人：——

  公开号：US8906908B2

  公开（公告）日：2014-12-09
• US9527823B2
  申请人：——

  公开号：US9527823B2

  公开（公告）日：2016-12-27