(R)-2-acetamido-3-(2-thienyl)propanoic acid | 83396-77-4

• 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: (R)-2-acetamido-3-(2-thienyl)propanoic acid
• 英文别名: (R)-N-acetyl-3-(2-thienyl)-alanine；(R)-N-acetyl-3-(2-thienyl)alanine；(R)-2-acetylamino-3-[2]thienyl-propionic acid；(R)-2-Acetylamino-3-[2]thienyl-propionsaeure；(2R)-2-acetamido-3-thiophen-2-ylpropanoic acid
• CAS: 83396-77-4
• 化学式: C₉H₁₁NO₃S
• 分子量: 213.257
• InChiKey: FSFVGPGABHYRPJ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (R)-2-acetamido-3-(2-thienyl)propanoic acid 在 盐酸 作用下， 反应 6.0h， 生成 3-(2-噻吩基)-D-丙氨酸
  参考文献：
  名称：

  Unusual amino acids IV. Asymmetric synthesis of thienylalanines

  摘要：

  (Z)-2-N-Acylamino-3-thienyl-acrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active 2-N-acetyl(or benzoyl)-3-(2- or 3-thienyl)-alanines with optical yields up to 90 % using the rhodium complexes of ''PROPRAPHOS'' 6a,b and O,N-bis(diphenylphosphino)-2-exo-hydroxy,3-endo-methylamino-norbornane 6c as chiral catalysts, Recrystallization and deacylation of the obtained amino acid derivatives yields the optically pure hydrochlorides of the thienylalanines and the free amino acids.

  DOI：

  10.1016/s0957-4166(00)80424-3
• 作为产物：
  描述：

  (Z)-2-Methyl-5-oxo-4-(2-thienylmethylene)-4,5-dihydro-1,3-oxazole 在 (-)-(R)-PROPRAPHOS rhodium 、 水 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 (R)-2-acetamido-3-(2-thienyl)propanoic acid
  参考文献：
  名称：

  Unusual amino acids IV. Asymmetric synthesis of thienylalanines

  摘要：

  (Z)-2-N-Acylamino-3-thienyl-acrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active 2-N-acetyl(or benzoyl)-3-(2- or 3-thienyl)-alanines with optical yields up to 90 % using the rhodium complexes of ''PROPRAPHOS'' 6a,b and O,N-bis(diphenylphosphino)-2-exo-hydroxy,3-endo-methylamino-norbornane 6c as chiral catalysts, Recrystallization and deacylation of the obtained amino acid derivatives yields the optically pure hydrochlorides of the thienylalanines and the free amino acids.

  DOI：

  10.1016/s0957-4166(00)80424-3

文献信息

• Dunn, Journal of Biological Chemistry, 1959, vol. 234, p. 802,803
  作者：Dunn

  DOI：——

  日期：——
• A Chiral 1,2-Bisphospholane Ligand with a Novel Structural Motif: Applications in Highly Enantioselective Rh-Catalyzed Hydrogenations
  作者：Wenjun Tang、Xumu Zhang

  DOI：10.1002/1521-3773(20020503)41:9<1612::aid-anie1612>3.0.co;2-h

  日期：2002.5.3
• Highly Enantioselective Rhodium-Catalyzed Hydrogenation of Dehydroamino Acids with New Chiral Bisphosphinites
  作者：Guoxin Zhu、Xumu Zhang

  DOI：10.1021/jo972268n

  日期：1998.5.1
• Influence of the heterocyclic ring on the asymmetric synthesis of .beta.-hetarylalanines by homogeneous catalytic hydrogenation
  作者：Carlos Cativiela、Jose A. Mayoral、Enrique Melendez、Luis A. Oro、Maria T. Pinillos、Rafael Uson

  DOI：10.1021/jo00187a042

  日期：1984.6