L-苯丙氨酸,N-(苯基亚甲基)-,乙基酯 | 137967-42-1

• 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
• 中文名称: L-苯丙氨酸,N-(苯基亚甲基)-,乙基酯
• 英文名称: ethyl (S)-2-(benzylideneamino)-3-phenylpropionate
• 英文别名: N-benzylidene-L-phenylalanine ethyl ester
• CAS: 137967-42-1
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: QZKLLIILJAQMCD-WFVLPUPGSA-N

物化性质

• 沸点：
  402.6±38.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸,N-(苯基亚甲基)-,乙基酯 在 盐酸 、 lithium hydroxide 、 正丁基锂 、 三甲基铝 、 碳酸氢钠 、 二异丙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 11.0h， 生成 1-[(N-methyl-N-benzyloxycarbonyl)amino]-3-benzyl-3-amino-2-azetidinone hydrochoride
  参考文献：
  名称：

  A general strategy for the synthesis of azapeptidomimetic lactams

  摘要：

  A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.029
• 作为产物：
  描述：

  L-苯丙氨酸乙酯盐酸盐 、 苯甲醛 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到L-苯丙氨酸,N-(苯基亚甲基)-,乙基酯
  参考文献：
  名称：

  A general strategy for the synthesis of azapeptidomimetic lactams

  摘要：

  A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.029

文献信息

• Regio- and Stereoselective 1,3-Dipolar Cycloadditions to 6<i>H</i>-1,2-Oxazines Leading to New Heterobicyclic Compounds
  作者：Hans-Ulrich Reissig、Elmar Schmidt、Reinhold Zimmer

  DOI：10.1055/s-2006-942403

  日期：2006.6

  exclusive formation of exo-configured products. 6H-1,2-Oxazines are therefore sufficiently reactive and selective dipolarophiles. The regioselectivity of the 1,3-dipolar cycloadditions is briefly discussed considering steric and electronic effects. PM3 calculations did not lead to fully satisfactory results in predicting the observed high regioselectivities. Preliminary subsequent reactions of the heterobicyclic

  典型的 1,3-偶极子，如腈氧化物、亚胺和叶立德，以及重氮烷烃、硝酮和甲亚胺叶立德，通常与 6H-1,2-恶嗪发生平滑的 [3+2] 环加成反应。杂双环加合物以中等至非常好的收率获得，具有优异的区域选择性和高非对映选择性。6H-1,2-恶嗪的 6-乙氧基取代基强烈地屏蔽了一个面，因此导致几乎完全形成外构型产品。因此，6H-1,2-恶嗪具有足够的反应性和选择性。考虑到空间和电子效应，简要讨论了 1,3-偶极环加成的区域选择性。PM3 计算在预测观察到的高区域选择性方面并未导致完全令人满意的结果。
• PROCESS FOR PRODUCTION OF MONO-SUBSTITUTED ALKYLATED COMPOUND USING ALDIMINE OR DERIVATIVE THEREOF
  申请人：Maruoka Keiji

  公开号：US20090054679A1

  公开（公告）日：2009-02-26

  The present invention provides a method for producing asymmetrical mono-substituted alkylated compounds of α-amino acids that are represented by a specific formula, using an aldimine-type Schiff base. In the method of the present invention, the process of alkylating an aldimine-type Schiff base in a medium in the presence of an optically-active quaternary ammonium salt phase-transfer catalyst and an inorganic base is initiated, and subsequently the reaction is quenched at a time earlier than a time for completion of the stoichiometric reaction of the alkylation reaction, so that a mono-substituted alkylated product with high optical purity can be obtained.

  本发明提供了一种使用醛亚胺型席夫碱制备α-氨基酸的不对称单取代烷基化合物的方法，其由特定的公式表示。在本发明的方法中，通过在存在光学活性季铵盐相转移催化剂和无机碱的介质中烷基化醛亚胺型席夫碱的过程，随后在达到化学计量反应完成时间之前的时间中止反应，从而可以获得具有高光学纯度的单取代烷基化产物。
• Boron trifluoride-assisted perfluoroalkylation of carbon-nitrogen double bonds
  作者：Hidemitsu Uno、Shinichiro Okada、Tetsushi Ono、Yasukazu Shiraishi、Hitomi Suzuki

  DOI：10.1021/jo00031a032

  日期：1992.2

  In the presence of BF3.OEt2, (perfluoroalkyl)lithiums generated in situ from the reaction of primary perfluoroalkyl iodides and MeLi-LiBr reacted with imines, azines, and nitrones to afford perfluoroalkylated nitrogen-containing compounds in moderate to good yields. This method was successfully applied to the preparation of a (perfluoroalkyl)glycine and optically active perfluoroalkylated amines.
• WO2007/13698
  申请人：——

  公开号：——

  公开（公告）日：——
• US8722919B2
  申请人：——

  公开号：US8722919B2

  公开（公告）日：2014-05-13