methyl (dimethylcarbamoyl)-L-phenylalaninate | 116129-85-2

• 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: methyl (dimethylcarbamoyl)-L-phenylalaninate
• 英文别名: methyl (2S)-2-(dimethylcarbamoylamino)-3-phenylpropanoate
• CAS: 116129-85-2
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: LHVOVMWAHAIETD-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (dimethylcarbamoyl)-L-phenylalaninate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 <(dimethylamino)carbonyl>-L-phenylalanine
  参考文献：
  名称：

  α-氨基腈的对映体去质子化/酰化

  摘要：

  回到“基本原理”：尽管立体不稳定的α-腈金属碳环化合物中间存在，但对映体富集的α-脲腈的标题反应仍以高度对映发散的方式进行。对映异构度取决于所用的碱。对于碱性较低的六甲基二硅叠氮化物（HMDS），提出了其中金属（M）阳离子与亲电试剂预配合的去质子化。LDA ＝二异丙基氨基锂。

  DOI：

  10.1002/anie.201306443
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 methyl (dimethylcarbamoyl)-L-phenylalaninate
  参考文献：
  名称：

  Renin inhibitors. Dipeptide analogs of angiotensinogen utilizing a structurally modified phenylalanine residue to impart proteolytic stability

  摘要：

  A series of renin inhibitors have been prepared and evaluated for their susceptibility to cleavage by the serine protease chymotrypsin. The compounds were designed by consideration of the structural requirements in the active-site region of renin and chymotrypsin. By systematic alteration of the P3 phenylalanine residue, compounds with varying degrees of renin inhibitory potency and chymotrypsin susceptibility were obtained. Selected analogues from this group were examined in vivo for both their hypotensive effects and metabolic patterns.

  DOI：

  10.1021/jm00120a006

文献信息

• Renin inhibitors. Dipeptide analogs of angiotensinogen utilizing a structurally modified phenylalanine residue to impart proteolytic stability
  作者：Jacob J. Plattner、Patrick A. Marcotte、Hollis D. Kleinert、Herman H. Stein、Jonathan Greer、Giorgio Bolis、Anthony K. L. Fung、Barbara A. Bopp、Jay R. Luly

  DOI：10.1021/jm00120a006

  日期：1988.12

  A series of renin inhibitors have been prepared and evaluated for their susceptibility to cleavage by the serine protease chymotrypsin. The compounds were designed by consideration of the structural requirements in the active-site region of renin and chymotrypsin. By systematic alteration of the P3 phenylalanine residue, compounds with varying degrees of renin inhibitory potency and chymotrypsin susceptibility were obtained. Selected analogues from this group were examined in vivo for both their hypotensive effects and metabolic patterns.
• Enantiodivergent Deprotonation/Acylation of α-Amino Nitriles
  作者：Michiko Sasaki、Tomo Takegawa、Kunihiro Sakamoto、Yuri Kotomori、Yuko Otani、Tomohiko Ohwada、Masatoshi Kawahata、Kentaro Yamaguchi、Kei Takeda

  DOI：10.1002/anie.201306443

  日期：2013.12.2

  title reaction of enantioenriched α‐ureidonitriles was found to proceed in a highly enantiodivergent manner despite the intermediacy of stereolabile α‐nitrile metallocarbanions. Enantiodivergence is dependent upon the base used. For the less basic hexamethyldisilazides (HMDS), deprotonation in which a metal (M) cation is precomplexed with an electrophile is proposed. LDA=lithium diisopropylamide.

  回到“基本原理”：尽管立体不稳定的α-腈金属碳环化合物中间存在，但对映体富集的α-脲腈的标题反应仍以高度对映发散的方式进行。对映异构度取决于所用的碱。对于碱性较低的六甲基二硅叠氮化物（HMDS），提出了其中金属（M）阳离子与亲电试剂预配合的去质子化。LDA ＝二异丙基氨基锂。