N-ethoxycarbonyl-L-phenylalaninol | 161646-29-3

• 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: N-ethoxycarbonyl-L-phenylalaninol
• 英文别名: (S)-ethyl (1-hydroxy-3-phenylpropan-2-yl)carbamate；ethyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• CAS: 161646-29-3
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: AVSCLOPFRCQQAR-NSHDSACASA-N

物化性质

• 沸点：
  400.3±38.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  N-ethoxycarbonyl-L-phenylalaninol 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢氧化钾 、 氢气 、 硝酸 、 乙酸酐 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 130.0h， 生成 (2S)-2-[2-[(2S)-2-amino-3-hydroxypropyl]anilino]-3-methylbutanoic acid
  参考文献：
  名称：

  Modeling, Chemistry, and Biology of the Benzolactam Analogues of Indolactam V (ILV). 2. Identification of the Binding Site of the Benzolactams in the CRD2 Activator-Binding Domain of PKCδ and Discovery of an ILV Analogue of Improved Isozyme Selectivity

  摘要：

  Protein kinase C (PKC) is a complex enzyme system comprised of at least II isozymes that serves to mediate numerous extracellular signals which generate lipid second messengers. The discovery of isozyme-selective activators and inhibitors (modulators) of PKC is crucial to ascertaining the role of the individual isozymes in physiological and pathophysiological processes and to manipulating their function. The discovery of such small molecule modulators of PKC is at present a largely unmet pharmacological need. Herein we detail our modeling studies which reveal how the natural product indolactam V (ILV) and its 8-membered ring analogue, the benzolactam 15, bind to the CRD2 activator domain of PKC. These modeling studies reveal that not all PKC ligands possess a common pharmacophore, and further suggest an important role of specific hydrophobic contacts in the PKC-ligand interaction, The modeling studies find strong experimental support from mutagenesis studies on PKC alpha that reveal the crucial role played by the residues proline 11, leucine 20, leucine 24, and glycine 27. Next, we describe the synthesis of two 8-substituted benzolactams starting from L-phenylalanine and characterize their isozyme selectivity; one of the two benzolactams exhibits improved isozyme selectivity relative to the n-octyl-ILV, Lastly, we report inhibition of cellular proliferation of two different breast carcinoma cell lines by the benzolactam 5 and show that the compound preferentially down-regulates PKC beta in both cell lines.

  DOI：

  10.1021/jm960875h
• 作为产物：
  描述：

  (S)-methyl 2-((ethoxycarbonyl)amino)-3-phenylpropanoate 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以97%的产率得到N-ethoxycarbonyl-L-phenylalaninol
  参考文献：
  名称：

  从 α-氨基酸制备手性 2-恶唑烷酮的简单有效方法

  摘要：

  摘要 描述了标题转化的改进程序，它避免了：(i) 潜在危险的硼烷还原步骤，和 (ii) 水溶性氨基醇的中间体。

  DOI：

  10.1080/00397919508011390

文献信息

• O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups
  作者：Osamu Tamura、Tomoyuki Suzuki、Kosaku Tanaka、Yoshimitsu Hashimoto、Nobuyoshi Morita

  DOI：10.1055/s-0039-1690856

  日期：2020.6

  Amino groups are selectively protected in good yields by reaction with O-alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.

  通过与 O-烷基 S-(吡啶-2-基)碳硫醇盐在适当的溶剂中在室温下在空气中反应，氨基以良好的产率被选择性地保护。甚至含有多个羟基的葡糖胺也在甲醇中被选择性地 N 保护。
• Copper-Catalyzed One-Pot Synthesis of <i>N</i>-Aryl Oxazolidinones from Amino Alcohol Carbamates
  作者：William Mahy、Pawel K. Plucinski、Christopher G. Frost

  DOI：10.1021/ol502322c

  日期：2014.10.3

  sequential intramolecular cyclization of amino alcohol carbamates followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions has been developed. The reaction occurred in good yields and tolerated aryl iodides containing functionalities such as nitriles, ketones, ethers, and halogens. Heteroaryl iodides and substituted amino alcohol carbamates were also well tolerated.

  已经开发出在氨基甲酸酯氨基甲酸酯的有效顺序分子内环化，然后在温和条件下与芳基碘化物进行铜催化的交叉偶联。该反应以高收率进行，并且可以耐受含有官能团（例如腈，酮，醚和卤素）的芳基碘化物。杂芳基碘化物和取代的氨基醇氨基甲酸酯也被很好地耐受。
• A Simple and Efficient Procedure for the Preparation of Chiral 2-Oxazolidinones from α-Amino Acids
  作者：Norman Lewis、Alexander McKillop、Richard J. K. Taylor、Robert J. Watson

  DOI：10.1080/00397919508011390

  日期：1995.2

  Abstract A modified procedure for the title transformation is described which avoids: (i) a potentially hazardous borane reduction step, and (ii) the intermediacy of water soluble amino alcohols.

  摘要 描述了标题转化的改进程序，它避免了：(i) 潜在危险的硼烷还原步骤，和 (ii) 水溶性氨基醇的中间体。
• Modified Mg : Al hydrotalcite in the synthesis of oxazolidin-2-ones
  作者：Agnieszka Cwik、Aliz Fuchs、Zoltán Hell、Ildikó Böjtös、Dóra Halmai、Petra Bombicz

  DOI：10.1039/b418848a

  日期：——

  The modified Mg : Al (3 : 1) hydrotalcite has been found to be an efficient catalyst in the conversion of carbamates into oxazolidin-2-ones under mild reaction conditions. A wide variety of oxazolidin-2-ones were obtained with excellent chemical yield.

  改性Mg : Al（3 : 1）水滑石已被证实是一种高效催化剂，在温和反应条件下能将氨基甲酸酯转化为噁唑烷-2-酮。多种噁唑烷-2-酮以优异的化学产率获得。
• 一种4-取代-2-恶唑烷酮的环合方法
  申请人：江苏万年长药业有限公司

  公开号：CN103539754B

  公开（公告）日：2016-01-20

  本发明公开了一种4-取代-2-恶唑烷酮的环合方法，是通过以下的步骤实现的：（1）酰化：在碳酸钾存在的条件下，在甲苯溶剂中将手性氨基醇采用氯甲酸酯进行酰化得到手性氨基醇酰化物；（2）环合：以PEG-400作为相转移催化剂进行环合反应到4-取代-2-恶唑烷酮。本发明的环合反应与现有技术相比，采用的相转移催化剂价格低廉，无危险性，缩短反应步骤，降低成本，条件温和，适宜工业化生产。