2-phenylglycinol hydrochloride | 62357-38-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-phenylglycinol hydrochloride
• 英文别名: 2-hydroxy-1-phenylethanaminium chloride；(+/-)-β-amino-phenethyl alcohol; hydrochloride；(+/-)-β-Amino-phenaethylalkohol; Hydrochlorid；(2-hydroxy-1-phenylethyl)azanium;chloride
• CAS: 62357-38-4
• 化学式: C₈H₁₁NO*ClH
• 分子量: 173.642
• InChiKey: KSXJJXIDBVLDBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  211-212 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 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：
  46.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenylglycinol hydrochloride 在 三氯氧磷 作用下， 生成 (+/-)-2-chloro-1-phenyl-ethylamine
  参考文献：
  名称：

  Bird,R. et al., Journal of the Chemical Society. Perkin transactions II, 1973, p. 1215 - 1220

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-oxo-4-phenyloxazolidine-3-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以70%的产率得到2-phenylglycinol hydrochloride
  参考文献：
  名称：

  Hydroxyamination of Olefins Using Br-N-(CO₂Me)₂

  摘要：

  The hydroxyamination reagent Br-N-(CO2Me)(2) underwent Markovnikov addition to various olefins in the presence of catalytic BF3 center dot OEt2 and provides efficient access to aminoalcohols. The reaction provided the trans-1-bromo, 2-N-bis-carbamate adduct stereoisomer in all cases. The resulting adduct underwent cyclization to give an oxazolidinone, which could be readily hydrolyzed to an oxazolidin-2-one or an amino alcohol.

  DOI：

  10.1021/jo502369d

文献信息

• Anionic Halocuprate(II) Complexes as Catalysts for the Oxaziridine-Mediated Aminohydroxylation of Olefins
  作者：Tamas Benkovics、Juana Du、Ilia A. Guzei、Tehshik P. Yoon

  DOI：10.1021/jo900902k

  日期：2009.8.7

  laboratories is dramatically accelerated in the presence of halide additives. The use of this more active catalyst system enables the efficient aminohydroxylation of electronically and sterically deactivated styrenes and also enables the use of nonstereogenic 3,3-dialkyl oxaziridines as terminal oxidants in the aminohydroxylation reaction. We present evidence that anionic halocuprate(II) complexes are the catalytically

  我们发现，最近在我们实验室中发现的恶氮丙啶介导的铜催化氨基羟基化反应在卤化物添加剂的存在下显着加速。使用这种活性更高的催化剂体系可以实现电子和空间失活苯乙烯的有效氨基羟基化，并且还可以使用非立体的 3,3-二烷基氧氮丙啶作为氨基羟基化反应中的末端氧化剂。我们提供的证据表明阴离子卤铜酸盐 (II) 复合物是催化活性物质，负责在这些条件下增加反应性。这一出人意料的观察使我们重新评估了我们对这种反应的机制理解。根据各种自由基捕获实验的结果，我们提出了一种改进的机制，该机制涉及烯烃与铜（II）活化的恶氮丙啶的均裂反应。总之，观察到阴离子添加剂显着提高了氧氮丙啶的氧化能力，并且认识到在这些条件下氧氮丙啶反应的自由基性质表明，由卤铜酸盐（II）配合物催化的各种新的氧化转化应该是可能的。
• Ruthenium‐Catalyzed Deaminative Hydrogenation of Amino Nitriles: Direct Access to 1,2‐Amino Alcohols
  作者：Pilar Calleja、Martin Ernst、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1002/chem.201900531

  日期：2019.7.17

  approach for the efficient and highly selective synthesis of 1,2‐amino alcohols by direct reductive hydrolysis of N‐formyl‐protected α‐amino nitriles is reported. The commercially available RuHCl(CO)(PPh3)3 complex was found to be a suitable catalyst for this operationally simple protocol, in which no stoichiometric amounts of undesired metal waste are generated. The deaminative hydrogenation is performed

  报道了一种通过N-甲酰基保护的α-氨基腈直接还原水解来高效，高选择性合成1,2-氨基醇的新方法。发现可商购获得的RuHCl（CO）（PPh 3）3络合物对于该操作简单的方案是合适的催化剂，其中不产生化学计量的不希望的金属废物。脱氨氢化反应在55 bar H 2下进行，使用1,4-二恶烷/水的6：1混合物作为溶剂。另外，在非常相似的条件下由氰基酮制备羟甲基醇。
• Stereoselectivity in the Salt-Cocrystal Products formed by Phenylglycinol or Phenylglycine with their Respective Sodium or Hydrochloride Salts
  作者：Harry G. Brittain

  DOI：10.1002/chir.22103

  日期：2013.1

  salt and stereoselective cocrystal phenomena associated with 2‐phenylglycinol and 2‐phenylglycine have been studied using X‐ray powder diffraction and differential scanning calorimetry. The chiral identities of the free acids and their sodium salts, or the free bases and their chloride salts, were found to play a determining role as to whether a salt–cocrystal product could or could not be formed. In particular

  使用X射线粉末衍射和差示扫描量热法研究了与2-苯基甘氨醇和2-苯基甘氨酸有关的盐和立体选择性共晶体现象。发现游离酸及其钠盐或游离碱及其氯化物盐的手性身份对是否可以形成盐-共结晶产物起决定性作用。特别是，当尝试对映体纯的碱性或两性离子物质与其对映体纯的酸加成盐进行共结晶时，只有当两种反应物的绝对构型相反时，才能获得盐-共晶。另一方面，手性25：8-15，2013年。分级为4 +©2012 Wiley Periodicals，Inc.
• Catalytic Chemo‐ and Regioselective Radical Carbocyanation of 2‐Azadienes for the Synthesis of α‐Amino Nitriles
  作者：Shengzu Duan、Ya Du、Lingling Wang、Xun Tian、Yujin Zi、Hongbin Zhang、Patrick J. Walsh、Xiaodong Yang

  DOI：10.1002/anie.202300605

  日期：——

  construction of complex α- and β-functionalized α-amino nitrile derivatives through a novel cascade strategy is presented. Alkyl radicals are generated by the photo-mediated reductive decarboxylation of redox-active esters, captured by 2-azadienes to provide 2-azallyl radicals and cyanized by a copper catalyst.

  提出了一种通过新型级联策略构建复杂 α- 和 β- 功能化 α- 氨基腈衍生物的温和且广泛适用的方法。烷基自由基由氧化还原活性酯的光介导还原脱羧作用产生，被 2-氮杂二烯捕获以提供 2-azallyl 自由基并被铜催化剂氰化。
• Oxazoline pseudodimers, pharmaceutical compositions and the use thereof
  申请人：PURDUE PHARMA L.P.

  公开号：US10858326B2

  公开（公告）日：2020-12-08

  The present disclosure is directed to oxazoline mono- and hetero-pseudodimer compounds, such as compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof: These compounds are useful for treating pain. The present disclosure also relates to pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of Formula (I) or (II) or a pharmaceutically acceptable salt or solvate thereof.

  本公开涉及噁唑啉单体和杂环假二聚体化合物，如式（I）化合物或其药学上可接受的盐或溶液： 这些化合物可用于治疗疼痛。本公开还涉及药物组合物，其中包含药学上可接受的载体和治疗有效量的式（I）或（II）化合物或其药学上可接受的盐或溶液。