(S)-methyl 2-amino-2-methyl-3-phenylpropanoate

• 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: (S)-methyl 2-amino-2-methyl-3-phenylpropanoate
• 英文别名: benzyl (2S)-2-amino-2-methyl-3-phenylpropanoate
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: LACQEWUOJSCMME-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-苯基-L-丙氨酸苄酯 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.08h， 生成 (S)-methyl 2-amino-2-methyl-3-phenylpropanoate
  参考文献：
  名称：

  具有手性Ansa结构和手性离子载体功能的吡P醛衍生物对α-氨基酯的不对称α-烷基化作用：双不对称诱导的一个新例子

  摘要：

  由α-氨基酯和在C-3上具有手性ansa结构和乙氧基乙氧基的吡ido醛模型制备的醛亚胺的立体选择性烷基化在Li +存在下进行，在酸性水解后得到α，α-二烷基氨基酯。通过手性ansa结构和C-3处的手性离子载体侧链的组合，在烷基化反应中还观察到双重不对称诱导作用。

  DOI：

  10.1016/s0040-4020(00)00392-6

文献信息

• Chiral environment specifically induced by metal ion: Asymmetric α-alkylation of α-amino esters using pyridoxal derivatives having a chiral ionophore function
  作者：Kazuyuki Miyashita、Hideto Miyabe、Kuninori Tai、Chiaki Kurozumi、Hiroshi Iwaki、Takeshi Imanishi

  DOI：10.1016/s0040-4020(99)00708-5

  日期：1999.10

  prepared from α-amino esters and pyridoxal models having an ionophoric side-chain composed of a chiral glycerol structure, proceeded in the presence of Li+ or Na+ to afford α,α-dialkyl amino esters after acidic hydrolysis. Both the structure of the side chain and the metal ion were found to be in relation with the stereoselectivity, affording the highest stereoselectivity when the side-chain having a 2-naphthylmethoxy

  由α-氨基酯和具有由手性甘油结构组成的离子性侧链的吡ation醛模型制备的醛亚胺的立体选择性烷基化在Li +或Na +存在下进行，在酸性水解后得到α，α-二烷基氨基酯。发现侧链的结构和金属离子均与立体选择性有关，当在各自的3'-和2'-分别具有2-萘甲氧基和甲氧基的侧链时，立体选择性最高。在Na +存在下进行职位定位。
• Asymmetric α-alkylation of α-amino esters using pyridoxal model compounds with a chiral ionophore function; dependence of stereoselectivity on a chelated metal ion
  作者：Kazuyuki Miyashita、Hideto Miyabe、Kuninori Tai、Chiaki Kurozumi、Takeshi Imanishi

  DOI：10.1039/cc9960001073

  日期：——

  Asymmetric alpha-alkylation of alpha-amino esters by use of novel pyridoxal model compounds having a chiral ionophore function is studied; the stereoselectivity is specifically induced by Na+ and the most effective asymmetric induction occurs with a combination of Na+ and an additional chiral ansa-structure.
• Synthesis of Quaternary α-Methyl α-Amino Acids by Asymmetric Alkylation of Pseudoephenamine Alaninamide Pivaldimine
  作者：Cedric L. Hugelshofer、Kevin T. Mellem、Andrew G. Myers

  DOI：10.1021/ol401337p

  日期：2013.6.21

  The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary alpha-methyl alpha-amino acids Is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide alpha-amino acids without salt contaminants. Alternatively, alpha-amino esters can be obtained by direct alcoholysis.
• Asymmetric α-Alkylation of α-Amino Esters Using Pyridoxal Derivatives Having a Chiral Ansa-Structure and a Chiral Ionophore Function: a Novel Example of Double Asymmetric Induction
  作者：Kazuyuki Miyashita、Hideto Miyabe、Kuninori Tai、Hiroshi Iwaki、Takeshi Imanishi

  DOI：10.1016/s0040-4020(00)00392-6

  日期：2000.6

  Stereoselective alkylation of aldimines, prepared from α-amino esters and a pyridoxal model having a chiral ansa-structure and an ethoxyethoxy group at C-3, proceeded in the presence of Li+ to give α,α-dialkyl amino esters after acidic hydrolysis. Double asymmetric induction effect was also observed in the alkylation reaction by combination of the chiral ansa-structure and a chiral ionophore side chain

  由α-氨基酯和在C-3上具有手性ansa结构和乙氧基乙氧基的吡ido醛模型制备的醛亚胺的立体选择性烷基化在Li +存在下进行，在酸性水解后得到α，α-二烷基氨基酯。通过手性ansa结构和C-3处的手性离子载体侧链的组合，在烷基化反应中还观察到双重不对称诱导作用。