(S)-2-[bis(4-methoxyphenyl)carbamoyl]-4-bromopent-4-enoic acid tert-butyl ester | 1229652-68-9

• 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: (S)-2-[bis(4-methoxyphenyl)carbamoyl]-4-bromopent-4-enoic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[bis(4-methoxyphenyl)carbamoyl]-4-bromopent-4-enoate
• CAS: 1229652-68-9
• 化学式: C₂₄H₂₈BrNO₅
• 分子量: 490.394
• InChiKey: ZKEXAWBFIFVAPF-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[bis(4-methoxyphenyl)carbamoyl]-4-bromopent-4-enoic acid tert-butyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到(S)-2-[bis(4-methoxyphenyl)carbamoyl]pent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of (−)-Paroxetine via Enantioselective Phase-Transfer Catalytic Monoalkylation of Malonamide Ester

  摘要：

  A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.

  DOI：

  10.1021/ol100928v
• 作为产物：
  描述：

  N,N-bis(4-methoxyphenyl)malonamic acid tert-butyl ester 、 2,3-二溴-1-丙烯 在 (11bS,11b’S)-2,6-bis(3,4,5-trifluorophenyl)-3,3’,5,5’-tetrahydro-4,4’-spirobi[dinaphtho[2,1-c:1’,2’-e]azepin]-4-ium bromide 、 potassium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 以99%的产率得到(S)-2-[bis(4-methoxyphenyl)carbamoyl]-4-bromopent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of (−)-Paroxetine via Enantioselective Phase-Transfer Catalytic Monoalkylation of Malonamide Ester

  摘要：

  A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.

  DOI：

  10.1021/ol100928v

文献信息

• Synthesis of (−)-Paroxetine via Enantioselective Phase-Transfer Catalytic Monoalkylation of Malonamide Ester
  作者：Mi-hyun Kim、Yohan Park、Byeong-Seon Jeong、Hyeung-geun Park、Sang-sup Jew

  DOI：10.1021/ol100928v

  日期：2010.6.18

  A new enantioselective synthetic method of (-)-paroxetine is reported. (-)-Paroxetine could be obtained in 15 steps (95% ee and 9.1% overall yield) from N,N-bis(p-methoxyphenyl)malonamide tert-butyl ester via the enantioselective phase-transfer catalytic alkylation and the diastereoselective Michael addition as the key steps.