(S)-N-carbethoxy-2-aminopropanoyl chloride | 79821-79-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-carbethoxy-2-aminopropanoyl chloride
• 英文别名: N-(ethoxycarbonyl)-L-alanine acid chloride；N-ethoxycarbonyl-L-alanyl chloride；EOC-L-Ala-Cl；ethyl N-[(2S)-1-chloro-1-oxopropan-2-yl]carbamate
• CAS: 79821-79-7
• 化学式: C₆H₁₀ClNO₃
• 分子量: 179.603
• InChiKey: RODOHZDRRRCQIP-BYPYZUCNSA-N

物化性质

• 沸点：
  250.7±23.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-carbethoxy-2-aminopropanoyl chloride 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  .alpha.-Amino acids as chiral educts for asymmetric products. Amino acylation with N-acylamino acids

  摘要：

  DOI：

  10.1021/ja00410a030
• 作为产物：
  描述：

  N-乙氧基羰基-L-丙氨酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-N-carbethoxy-2-aminopropanoyl chloride
  参考文献：
  名称：

  α-氨基酮的硼氢化锌还原：抗-γ-羟基-β-氨基醇的高度非对映选择性合成途径

  摘要：

  本研究介绍了通过 Zn(BH4)2 还原丝氨酸衍生的 δ- 氨基酮，高非对映选择性合成抗δ-羟基δ-氨基醇的方法。后者是由丝氨酸衍生的δ±-氨基酮通过δ-烷基化-脱硫顺序制备的。

  DOI：

  10.1055/s-2001-16773

文献信息

• L-aspartic acid bis(trimethylsilyl) ester: a convenient starting material for the acylation of L-aspartic acid.
  作者：Ana M. Castano、Antonio M. Echavarren

  DOI：10.1016/0040-4020(92)85013-5

  日期：1992.1

  Reaction of L-aspartic acid with excess of bis(trimethylsilyl)amine under reflux provides optically pure L-aspartic acid bis(trimethylsilyl) ester in quantitative yield. This silyl ester reacts with a variety of acylating reagens in tetrahydrofuran to give N-protected aspartic acids and dipeptides in good yields without racemization.

  L-天冬氨酸与过量的双（三甲基甲硅烷基）胺的反应在回流下以定量收率提供了光学纯的L-天冬氨酸双（三甲基甲硅烷基）酯。该甲硅烷基酯与四氢呋喃中的各种酰化反应物反应，以高收率得到N-保护的天冬氨酸和二肽，而没有外消旋作用。
• Synthesis of chiral n-protected α-amino-β-diketones from α-diazoketones derived from natural amino acids
  作者：Tao Ye、M.Anthony McKervey

  DOI：10.1016/s0040-4020(01)80473-7

  日期：1992.1

  Alpha-Diazoketols, prepared by condensation of aldehydes or ketones with lithiated optically active alpha-diazoketones derived from natural amino acids, rearrange to homochiral alpha-amino-beat-diketones on treatment with rhodium(II) acetate.
• .alpha.-Amino acids as chiral educts for asymmetric products. The synthesis of .alpha.'-amino-.alpha.,.beta.-ynones
  作者：Thomas L. Cupps、Raymond H. Boutin、Henry Rapoport

  DOI：10.1021/jo00221a004

  日期：1985.10
• Synthesis and Antitumor Activity of Enantiomerically Pure [1, 2-Diamino-1-(4-fluorophenyl) propane]dichloroplatinum(II) Complexes
  作者：Francois Dufrasne、Michael Gelbcke、Beate Schnurr、Ronald Gust

  DOI：10.1002/1521-4184(200205)335:5<229::aid-ardp229>3.0.co;2-q

  日期：2002.5

  Enantiomericaily pure 1,2-diamino-1-(4-fluorophenyl)propanes were synthesized by stereospecific and stereoselective procedures by use of the (1R,2S)- and (1S,2R)-2-amino-1-(4-fluorophenyl)propanols (12a) as intermediates. The enantiomeric purity was determined by H-1 NMR spectroscopy after conversion of the propanolamines and the diamines with (1R)-myrtenal into mono- and diimines. For the coordination to platinum the diamines were reacted with K2PtCl4. The resulting dichloroplatinum(II) complexes 4F-Ph/Me-PtCl2 were tested for antiproliferative activity on the MCF-7 breast cancer cell line. (SS)- and (RR)-4F-Ph/Me-PtCl2 produced the strongest inhibitory effect. Both complexes showed cytocidal effects, (SS)-4F-Ph/Me-PtCl2 even in a concentration of 1 muM. The (1S,2R)- and (1R,2S)-configurated complexes were far less active (SS>RR>RS=SR) and comparable in this respect with the standard cisplatin.
• Kinetic resolution of dl-2,3-epoxy alcohols using chiral titanium complex with amino alcohol derived ligand
  作者：Akira Ishikawa、Tsutomu Katsuki

  DOI：10.1016/0040-4039(91)80829-u

  日期：1991.7

  Highly effective kinetic resolution of primary dl-2,3-epoxy alcohols such as 2,3-epoxygeraniol and 2,3-epoxynerol was realized by using a combination of Ti(O(i)Pr)4 and (1R,2S)-2-(p-toluenesulfonylamino)-1-(2,4,6-trimethylphenyl)-1-propanol as a chiral Lewis acid catalyst.