(2R,3R,3'R)-2,3-dihydro-2,7-dimethyl-3-<3'-((R)-N-acetyl-O-methylcystein-S-yl)ethyl>-8-<2-(methoxycarbonyl)ethyl>-9-formylpyrromethenone-5-carboxylic acid | 135614-49-2

• 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: (2R,3R,3'R)-2,3-dihydro-2,7-dimethyl-3-<3'-((R)-N-acetyl-O-methylcystein-S-yl)ethyl>-8-<2-(methoxycarbonyl)ethyl>-9-formylpyrromethenone-5-carboxylic acid
• CAS: 135614-49-2
• 化学式: C₂₅H₃₃N₃O₉S
• 分子量: 551.618
• InChiKey: LKPOFJLDNCTVCK-YDZJCURKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  180.96
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,3'R)-2,3-dihydro-2,7-dimethyl-3-<3'-((R)-N-acetyl-O-methylcystein-S-yl)ethyl>-8-<2-(methoxycarbonyl)ethyl>-9-formylpyrromethenone-5-carboxylic acid 在 氢溴酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 18.0h， 生成 (2R,3R,3'R)-3'-((R)-N-acetyl-O-methylcystein-S-yl)-3,3'-dihydrophycocyanobilin dimethyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of phycocyanobilin-cysteine adducts

  摘要：

  Methodology is presented for the synthesis of two diastereomers of a cysteine-linked phycocyanobilin derivative. The crucial reaction is a diastereoselective 1,6-Michael addition of cysteine methyl ester to an appropriate dihydropyrromethenone educt. The diastereomers so generated were then elaborated to two phycocyanobilin trimethyl esters. Definitive assignments of relative stereochemistry, double bond geometry, and solution conformation are accomplished by application of ROESY NMR experiments, while absolute stereochemical assignments are based on degradation to compounds of known chirality.

  DOI：

  10.1021/ja00021a032
• 作为产物：
  描述：

  tert-butyl 5-((Z)-2-(tert-butoxy)-1-((E)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene)-2-oxoethyl)-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrole-2-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.84h， 生成 (2R,3R,3'R)-2,3-dihydro-2,7-dimethyl-3-<3'-((R)-N-acetyl-O-methylcystein-S-yl)ethyl>-8-<2-(methoxycarbonyl)ethyl>-9-formylpyrromethenone-5-carboxylic acid
  参考文献：
  名称：

  Diastereoselective synthesis of phycocyanobilin-cysteine adducts

  摘要：

  Methodology is presented for the synthesis of two diastereomers of a cysteine-linked phycocyanobilin derivative. The crucial reaction is a diastereoselective 1,6-Michael addition of cysteine methyl ester to an appropriate dihydropyrromethenone educt. The diastereomers so generated were then elaborated to two phycocyanobilin trimethyl esters. Definitive assignments of relative stereochemistry, double bond geometry, and solution conformation are accomplished by application of ROESY NMR experiments, while absolute stereochemical assignments are based on degradation to compounds of known chirality.

  DOI：

  10.1021/ja00021a032