methyl β-cyanoalanate hydrochloride | 1007217-05-1

• 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
• 英文名称: methyl β-cyanoalanate hydrochloride
• 英文别名: methyl (2S)-2-amino-3-cyanopropanoate;hydrochloride
• CAS: 1007217-05-1
• 化学式: C₅H₈N₂O₂*ClH
• 分子量: 164.592
• InChiKey: QVHAHQHYVQEIQP-WCCKRBBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl β-cyanoalanate hydrochloride 、 (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-(4-chlorophenyl)-2-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]propanoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以252 mg的产率得到methyl (2S)-2-[[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-(4-chlorophenyl)-2-[[(2R)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]propanoyl]amino]-3-cyanopropanoate
  参考文献：
  名称：

  Synthesis of a Key Precursor for Orienticin C and Model Study on Ruthenium-Mediated Macrocyclization

  摘要：

  [GRAPHICS]A tripeptido-arene-ruthenium complex was prepared as a key precursor for the projected synthesis of orienticin C, demonstrating that the cyclopentadienylruthenium moiety can be attached to a chloroarene in the presence of multiple functionality. The ruthenium-mediated intramolecular SNAr reaction for formation of the required diaryl ether linkage was successfully tested on a model system.

  DOI：

  10.1021/jo702245z
• 作为产物：
  描述：

  methyl (S)-2-((t-butoxycarbonyl)amino)-3-cyanopropanoate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以100%的产率得到methyl β-cyanoalanate hydrochloride
  参考文献：
  名称：

  Synthesis of a Key Precursor for Orienticin C and Model Study on Ruthenium-Mediated Macrocyclization

  摘要：

  [GRAPHICS]A tripeptido-arene-ruthenium complex was prepared as a key precursor for the projected synthesis of orienticin C, demonstrating that the cyclopentadienylruthenium moiety can be attached to a chloroarene in the presence of multiple functionality. The ruthenium-mediated intramolecular SNAr reaction for formation of the required diaryl ether linkage was successfully tested on a model system.

  DOI：

  10.1021/jo702245z