(2-hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester | 152547-74-5

• 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: (2-hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester
• 英文别名: (1R,2R)-2-(tert-butoxycarbonyl-amino)-1-phenyl-propan-1-ol；tert-butyl N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]carbamate
• CAS: 152547-74-5
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: XQMKOBSKWGMZQO-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以86%的产率得到(R)-t-butyl [1-phenyl-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Enantioselective Synthesis of Both Enantiomers of Cathinone via the Microbiological Reduction of 2-Azido-1-phenyl-1-propanone

  摘要：

  DOI：

  10.1021/jo00105a060
• 作为产物：
  描述：

  1-羟基-1-苯乙酮 在 4-二甲氨基吡啶 、 potassium cyanide 、 甲酸 、 (1S,2S)-Cp*RhCl(TsNCHPhCHPhNH₂) 、 氨基磺酰氯 、 对甲苯磺酸 、 三乙胺 、 cesium fluoride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.92h， 生成 (2-hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Norephedrine and Norpseudoephedrine by Using Asymmetric Transfer Hydrogenation Accompanied by Dynamic Kinetic Resolution

  摘要：

  Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO2H/Et3N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.

  DOI：

  10.1021/jo300867y

文献信息

• Experimental and DFT study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism
  作者：Abdelkarim El Moncef、El Mestafa El Hadrami、Miguel A. González、Elena Zaballos、Ramón J. Zaragozá

  DOI：10.1016/j.tet.2010.04.097

  日期：2010.7

  Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and/or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated

  磺化1,2-氨基醇的N -Boc衍生物，如麻黄碱，伪麻黄碱，去甲麻黄碱，去甲伪麻黄碱，硫代米胺和氯霉素，可得到相应的恶唑烷酮的混合物，具有倒置（赤型衍生物）和/或保留构型（苏式衍生物） ）在C5。我们建议两种机制之间的竞争：通过Boc基团的羰基氧攻击苄基碳引发的分子内S N 2过程，以及通过双重S N 2过程进行的另一种分子内S N 2过程。在赤型衍生物中，第一个机理是主要的，而在苏氨酸中，第一个机理是主要的。两种机制的导数具有相似的能量。这一假设得到理论计算和其他实验分析的支持。
• Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity
  作者：Claude Agami、François Couty、Louis Hamon、Olivier Venier

  DOI：10.1016/0040-4039(93)88071-p

  日期：1993.7

  Treatment of N-tert-butoxycarbonyl derivatives of homochiral β-amino alcohols with p-toluenesulfonyl chloride affords 2-axazolidinones. These heterocycles were produced by intramolecular nucleophilic attack of the carbamate moiety in an intermediate tosylate. The presence of a N-methyl substituent enhanced the cyclization rate and this effect was studied by AM1 calculations.

  用对甲苯磺酰氯处理高手性β-氨基醇的N-叔丁氧基羰基衍生物，得到2-ax唑烷酮。这些杂环是通过中间体甲苯磺酸酯中氨基甲酸酯部分的分子内亲核攻击产生的。N-甲基取代基的存在增强了环化速率，并且通过AM1计算研究了该效应。
• Stereocontrolled Synthesis of β-Amino Alcohols from Lithiated Aziridines and Boronic Esters
  作者：Frank Schmidt、Florian Keller、Emeline Vedrenne、Varinder K. Aggarwal

  DOI：10.1002/anie.200805272

  日期：2009.1.26

  β‐Amino alcohols have been prepared with high selectivity by the addition of lithiated aziridines to boronic esters. The regioselectivity of lithiation for aryl aziridines is sensitive to the reaction conditions and to the base employed. This response was exploited to give either class of β‐amino alcohols (see scheme; Boc=tert‐butoxycarbonyl, Bus=tert‐butylsulfonyl, LTMP=lithium 2,2,6,6‐tetramethylpiperidide

  通过向硼酸酯中添加锂化氮丙啶，可以高选择性地制备β-氨基醇。芳基氮丙啶的锂化的区域选择性对反应条件和所用碱敏感。利用该响应来生成任一类β-氨基醇（参见方案； Boc =叔丁氧基羰基，Bus =叔丁基磺酰基，LTMP = 2,2,6,6-四甲基哌啶锂，pin =频哪醇）。
• Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones
  作者：Shweta K. Gediya、Guy J. Clarkson、Martin Wills

  DOI：10.1021/acs.joc.0c01438

  日期：2020.9.4

  A series of α-amino ketones were reduced using asymmetric transfer hydrogenation (ATH) through a dynamic kinetic resolution (DKR). The protecting group was matched to the reducing agent, and following optimization, a series of substrates were investigated, giving products in high diastereoselectivity, over 99% ee in several cases and full conversion. The methodology was applied to the enantioselective

  使用不对称转移氢化（ATH）通过动态动力学拆分（DKR）还原了一系列α-氨基酮。使保护基与还原剂匹配，并在优化后对一系列底物进行了研究，从而获得了具有高非对映选择性的产品，在某些情况下具有超过99％ee的产物并实现了完全转化。该方法应用于MDM2-p53抑制剂前体的对映选择性合成。
• The use of phosphinamide N-protecting groups in the diastereoselective reduction of ketones
  作者：Matthew J. Palmer、John R. Studley、Tim C. Walsgrove、Martin Wills

  DOI：10.1016/s0040-4039(97)00302-x

  日期：1997.3

  The phosphinamide N-protecting group is demonstrated to be an effective directing group for the diastereoselective reductions of proximal ketones.

  证明次膦酰胺N-保护基是用于非对映选择性还原近端酮的有效指导基团。