tert-butyl [4-[[(2R)-1-[(E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoyl]-5-oxo-2H-pyrrol-2-yl]methyl]phenyl] carbonate | 1190758-13-4

• 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: tert-butyl [4-[[(2R)-1-[(E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoyl]-5-oxo-2H-pyrrol-2-yl]methyl]phenyl] carbonate
• CAS: 1190758-13-4
• 化学式: C₃₁H₄₄N₂O₇
• 分子量: 556.7
• InChiKey: ILCROIVXTCTKJY-CYBWEPMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl [4-[[(2R)-1-[(E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoyl]-5-oxo-2H-pyrrol-2-yl]methyl]phenyl] carbonate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以42%的产率得到(R)-N-(5-(2-(4-hydroxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3,5-dioxopentyl)-6,6-dimethylheptanamide
  参考文献：
  名称：

  Enantioselective Synthesis of the R-Enantiomer of the Feeding Deterrent (S)-Ypaoamide

  摘要：

  The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment, and a lipase (CCL)-promoted deacetylation reaction to reach the orthogonal deprotection. Through this work the absolute configuration of the natural ypaoamide was determined as S.

  DOI：

  10.1021/jo901557h
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 N-[(E)-5-((2R,3S)-2-(4-hydroxybenzyl)-3-hydroxy-5-oxopyrrolidin-1-yl)-3-methoxy-5-oxopent-3-enyl]-6,6-dimethylheptanamide 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到tert-butyl [4-[[(2R)-1-[(E)-5-(6,6-dimethylheptanoylamino)-3-methoxypent-2-enoyl]-5-oxo-2H-pyrrol-2-yl]methyl]phenyl] carbonate
  参考文献：
  名称：

  Enantioselective Synthesis of the R-Enantiomer of the Feeding Deterrent (S)-Ypaoamide

  摘要：

  The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment, and a lipase (CCL)-promoted deacetylation reaction to reach the orthogonal deprotection. Through this work the absolute configuration of the natural ypaoamide was determined as S.

  DOI：

  10.1021/jo901557h

文献信息

• Enantioselective Synthesis of the <i>R</i>-Enantiomer of the Feeding Deterrent (<i>S</i>)-Ypaoamide
  作者：Jie Chen、Pei-Qiang Huang、Yves Queneau

  DOI：10.1021/jo901557h

  日期：2009.10.2

  The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment, and a lipase (CCL)-promoted deacetylation reaction to reach the orthogonal deprotection. Through this work the absolute configuration of the natural ypaoamide was determined as S.