(+/-)-2-chloro-1-phenyl-ethylamine | 42331-00-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-2-chloro-1-phenyl-ethylamine
• 英文别名: (+/-)-2-Chlor-1-phenyl-aethylamin；β-Chlor-α-phenyl-aethylamin；2-Chlor-1-amino-1-phenyl-aethan；2-Chlor-1-phenyl-aethylamin；β-Chlor-α-amino-α-phenyl-aethan；α-Phenyl-β-chlor-ethylamin；2-Chloro-1-phenylethanamine
• CAS: 42331-00-0
• 化学式: C₈H₁₀ClN
• 分子量: 155.627
• InChiKey: YZLUVSDGJWNNQY-UHFFFAOYSA-N

物化性质

• 沸点：
  231.1±28.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-2-chloro-1-phenyl-ethylamine 在 水 作用下， 生成 2-苯基氮丙啶
  参考文献：
  名称：

  Gabriel; Colman, Chemische Berichte, 1914, vol. 47, p. 1870

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 、 三氯化磷 作用下， 生成 (+/-)-2-chloro-1-phenyl-ethylamine
  参考文献：
  名称：

  Gabriel; Colman, Chemische Berichte, 1914, vol. 47, p. 1870

  摘要：

  DOI：

文献信息

• Chlorination/Cyclodehydration of Amino Alcohols with SOCl₂:  An Old Reaction Revisited
  作者：Feng Xu、Bryon Simmons、Robert A. Reamer、Edward Corley、Jerry Murry、David Tschaen

  DOI：10.1021/jo701877h

  日期：2008.1.1

  A simple, one-pot preparation of cyclic amines via efficient chlorination of amino alcohols with use of SOCl2 has been developed. This approach obviates the need for the classical N-protection/O-activation/cyclization/deprotection sequence commonly employed for this type of transformation. The reaction pathways and the general scope of this method have also been investigated.

  已经开发出一种简单的一锅法，通过使用SOCl 2对氨基醇进行有效氯化来制备环胺。该方法消除了通常用于这种类型的转化的经典的N-保护/ O-活化/环化/去保护序列的需要。还研究了该方法的反应途径和一般范围。
• Asymmetric Synthesis of Chiral Primary Amines by Transfer Hydrogenation of <i>N</i>-(<i>tert</i>-Butanesulfinyl)ketimines
  作者：David Guijarro、Óscar Pablo、Miguel Yus

  DOI：10.1021/jo101057s

  日期：2010.8.6

  The diastereoselective reduction of (R)-N-(tert-butanesulfinyl)ketimines by a ruthenium-catalyzed asymmetric transfer hydrogenation process in isopropyl alcohol, followed by desulfinylation of the nitrogen atom, is an excellent method to prepare highly enantiomerically enriched α-branched primary amines (up to >99% ee) in short reaction times (1−4 h). (1S,2R)-1-Amino-2-indanol has been shown to be

  钌催化的异丙醇中钌催化的不对称转移氢化过程，对非对映选择性还原（R）-N-（叔丁烷亚磺酰基）酮亚胺，然后对氮原子进行脱亚磺酰化，是制备高度对映体富集的α-支化伯伯伯醇的绝佳方法在短的反应时间（1-4小时）内可吸收胺（ee高达99％以上）。（1秒，2 R）-1-氨基-2-茚满醇已被证明是进行这种转化的非常有效的配体。带有芳基或杂芳基和烷基作为亚胺基碳原子的取代基的酮亚胺是该方法非常好的底物。还可以实现二烷基酮亚胺的还原，从而提供具有中等旋光纯度（69％ee）的预期胺。已经以优异的产率和过量的对映体制备了一些胺，它们是非常令人感兴趣的生物学和药理学活性化合物的前体。
• Design, Synthesis, and Structure−Activity Relationships of 1-,3-,8-, and 9-Substituted-9-deazaxanthines at the Human A_2B Adenosine Receptor
  作者：Angelo Carotti、Maria Isabel Cadavid、Nuria B. Centeno、Cristina Esteve、Maria Isabel Loza、Ana Martinez、Rosa Nieto、Enrique Raviña、Ferran Sanz、Victor Segarra、Eddy Sotelo、Angela Stefanachi、Bernat Vidal

  DOI：10.1021/jm0506221

  日期：2006.1.1

  Over two hundred 1-, 3-, 8-, and 9-substituted-9-deazaxanthines were prepared and evaluated for their binding affinity at the recombinant human adenosine receptors, in particular at the hA(2B) and hA(2A) subtypes. Several ligands endowed with sub-micromolar to low nanomolar binding affinity at hA(2B) receptors, good selectivity over hA(2A) and hA(3), but a relatively poor selectivity over hA(1) were obtained. Good antagonistic potencies and efficacies, with pA(2) values close to the corresponding pK(i)s, were observed in functional assays in vitro performed on a selected series of compounds. 1,3-Dimethyl-8-phenoxy-(N-p-halogenophenyl)-acetamido-9-deazaxanthine derivatives appeared as the most interesting leads, some of them showing outstanding hA(2B) affinities, high selectivity over hA(2A) and hA(3), but low selectivity over hA(1). Structure-affinity relationships suggested that the binding potency at the hA(2B) receptor was mainly modulated by the steric (lipophilic) properties of the substituents at positions 1 and 3 and by the electronic and lipophilic characteristics of the substituents at position 8. A comparison among affinity and selectivity profiles of 9-deazaxanthines with the corresponding xanthines suggested some possible differences in their binding mode.
• One-Pot Preparation of Cyclic Amines from Amino Alcohols
  作者：Xu, Feng、Simmons, Bryon

  DOI：10.15227/orgsyn.090.0251

  日期：——
• Aminophenyl-2-oxazolines as Local Anesthetics
  作者：M. T. Leffler、Roger Adams

  DOI：10.1021/ja01290a042

  日期：1937.11