(4S)-3,4-dihydro-4-phenyl-1(2H)-naphthalenone | 91797-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (4S)-3,4-dihydro-4-phenyl-1(2H)-naphthalenone
• 英文别名: 4-phenyl-1-tetralone；(4S)-4-phenyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 91797-70-5
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: YQUCNHUJKOVKNR-ZDUSSCGKSA-N

物化性质

• 沸点：
  351.0±32.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1R,4S)-N-甲基-4-苯基-1,2,3,4-四氢-1-萘胺 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 (4S)-3,4-dihydro-4-phenyl-1(2H)-naphthalenone
  参考文献：
  名称：

  衍生自顺式和反式-1-氨基-4-芳基四氢化萘的非三环抗抑郁药。

  摘要：

  对缺乏三环抗抑郁药的引人注目的和局限性副作用的药物的需求促使人们寻找对选择性机制的选择性大大增强的药物，这些特定机制对于抗抑郁药的功效至关重要。长期以来，人们一直怀疑5-HT途径紊乱在抑郁症病因中的潜在作用，并推动了新型化合物的发展，这些化合物强调了5-羟色胺再摄取的抑制作用。本文介绍了一系列顺式-1-氨基-4-（取代-芳基）四氢萘的构效关系，这在体外模型中是5-羟色胺摄取的强效和选择性抑制剂。这些化合物在药理上不同于反式系列的相应成员，后者也有效地阻止了多巴胺和去甲肾上腺素的吸收。

  DOI：

  10.1021/jm00377a021

文献信息

• Efficient Kinetic Resolution in the Asymmetric Hydrosilylation of Imines of 3-Substituted Indanones and 4-Substituted Tetralones
  作者：Jaesook Yun、Stephen. L. Buchwald

  DOI：10.1021/jo991328h

  日期：2000.2.1

  Kinetic resolution of the N-methyl imines of 3-substituted indanones and 4-substituted tetralones could be accomplished by hydrosilylation with a chiral titanocene catalyst. N-Methyl imines of 4-substituted tetralones were resolved to yield, after hydrolysis of the unreacted starting materials, ketones with high ee's and the amine products with high diastereomeric and enantiomeric purity. The utility of this process was demonstrated in the synthesis of sertraline.
• Origin of Stereocontrol in Guanidine-Bisurea Bifunctional Organocatalyst That Promotes α-Hydroxylation of Tetralone-Derived β-Ketoesters: Asymmetric Synthesis of β- and γ-Substituted Tetralone Derivatives via Organocatalytic Oxidative Kinetic Resolution
  作者：Minami Odagi、Kota Furukori、Yoshiharu Yamamoto、Makoto Sato、Keisuke Iida、Masahiro Yamanaka、Kazuo Nagasawa

  DOI：10.1021/ja511149y

  日期：2015.2.11

  The mechanism of asymmetric a-hydroxylation of tetralone-derived beta-ketoesters with guanidine-bisurea bifunctional organocatalyst in the presence of cumene hydroperoxide (CHP) was examined by means of DFT calculations to understand the origin of the stereocontrol in the reaction. The identified transition-state model was utilized to design an enantioselective synthesis of beta- or gamma-substituted tetralones by catalytic oxidative kinetic resolution reaction of tetralone-derived beta-ketoesters. This kinetic resolution reaction proceeded with high selectivity, and selectivity factors (s value) of up to 99 were obtained. The potential utility of this oxidative kinetic resolution method for synthesis of natural products was confirmed by applying it to achieve an enantioselective synthesis of (+)-linoxepin (13) from beta-substituted tetralone rac-7 in only six steps.
• WELCH, W. M.;KRASKA, A. R.;SARGES, R.;KOE, B. K., J. MED. CHEM., 1984, 27, N 11, 1508-1515
  作者：WELCH, W. M.、KRASKA, A. R.、SARGES, R.、KOE, B. K.

  DOI：——

  日期：——
• Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins
  作者：Willard M. Welch、Allen R. Kraska、Reinhard Sarges、B. Kenneth Koe

  DOI：10.1021/jm00377a021

  日期：1984.11

  of the tricyclic antidepressants has prompted the search for agents with greatly enhanced selectivity for specific mechanisms believed to be essential for antidepressant efficacy. The potential role of derangements of 5-HT pathways in the etiology of depression has long been suspected and has given impetus to the development of newer compounds that accentuate inhibition of serotonin reuptake. This paper

  对缺乏三环抗抑郁药的引人注目的和局限性副作用的药物的需求促使人们寻找对选择性机制的选择性大大增强的药物，这些特定机制对于抗抑郁药的功效至关重要。长期以来，人们一直怀疑5-HT途径紊乱在抑郁症病因中的潜在作用，并推动了新型化合物的发展，这些化合物强调了5-羟色胺再摄取的抑制作用。本文介绍了一系列顺式-1-氨基-4-（取代-芳基）四氢萘的构效关系，这在体外模型中是5-羟色胺摄取的强效和选择性抑制剂。这些化合物在药理上不同于反式系列的相应成员，后者也有效地阻止了多巴胺和去甲肾上腺素的吸收。