ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate | 908254-64-8

• 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: ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate
• 英文别名: ethyl (Z)-6-(4-chlorophenyl)-6-(phenylmethoxycarbonylamino)-4-propan-2-ylhex-4-en-2-ynoate
• CAS: 908254-64-8
• 化学式: C₂₅H₂₆ClNO₄
• 分子量: 439.939
• InChiKey: XGQLQNOGWKTRSG-LTGZKZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到ethyl [1-benzyloxycarbonyl-3-isopropyl-5-(4-chlorophenyl)pyrrol-2-yl]acetate
  参考文献：
  名称：

  Efficient Synthesis of 1,3,5-Trisubstituted (Pyrrol-2-yl)acetic Acid Esters via Dual Nucleophilic Reactions of Sulfonamides or Carbamate with 4-Trimethyl-siloxy-(5E)-hexen-2-ynoates:  Lewis Acid Catalyzed S_N1 and Intramolecular Michael Addition

  摘要：

  Carbamates or sulfonamides have proven to regioselectively attack 2-propynyl-allyl hybrid cations, generated by the action of TMSOTf on 4-(trimethylsioxy)hex-5-en-2-ynoates, to afford conjugated 6-aminohex-4-en-2-ynoates in which an intramolecular amino-Michael reaction took place, leading to pyrrole frameworks. In particular, the sulfonamides gave 1-sulfonylpyrroles in one pot.

  DOI：

  10.1021/ol0616485
• 作为产物：
  描述：

  (E)-1-(4-chlorophenyl)-4-methylpent-1-en-3-one 在 咪唑 、 正丁基锂 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate
  参考文献：
  名称：

  Efficient Synthesis of 1,3,5-Trisubstituted (Pyrrol-2-yl)acetic Acid Esters via Dual Nucleophilic Reactions of Sulfonamides or Carbamate with 4-Trimethyl-siloxy-(5E)-hexen-2-ynoates:  Lewis Acid Catalyzed S_N1 and Intramolecular Michael Addition

  摘要：

  Carbamates or sulfonamides have proven to regioselectively attack 2-propynyl-allyl hybrid cations, generated by the action of TMSOTf on 4-(trimethylsioxy)hex-5-en-2-ynoates, to afford conjugated 6-aminohex-4-en-2-ynoates in which an intramolecular amino-Michael reaction took place, leading to pyrrole frameworks. In particular, the sulfonamides gave 1-sulfonylpyrroles in one pot.

  DOI：

  10.1021/ol0616485

文献信息

• Efficient Synthesis of 1,3,5-Trisubstituted (Pyrrol-2-yl)acetic Acid Esters via Dual Nucleophilic Reactions of Sulfonamides or Carbamate with 4-Trimethyl-siloxy-(5<i>E</i>)-hexen-2-ynoates:  Lewis Acid Catalyzed S_N1 and Intramolecular Michael Addition
  作者：Teruhiko Ishikawa、Toshiaki Aikawa、Shinichiro Watanabe、Seiki Saito

  DOI：10.1021/ol0616485

  日期：2006.8.1

  Carbamates or sulfonamides have proven to regioselectively attack 2-propynyl-allyl hybrid cations, generated by the action of TMSOTf on 4-(trimethylsioxy)hex-5-en-2-ynoates, to afford conjugated 6-aminohex-4-en-2-ynoates in which an intramolecular amino-Michael reaction took place, leading to pyrrole frameworks. In particular, the sulfonamides gave 1-sulfonylpyrroles in one pot.