N,N'-Bis<(1S)-1-(hydroxymethyl)-2-methylpropyl>-2,2-diethyl-1,3-propanediamide bismesylate | 169769-07-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N'-Bis<(1S)-1-(hydroxymethyl)-2-methylpropyl>-2,2-diethyl-1,3-propanediamide bismesylate
• 英文别名: [(2S)-2-[[2-ethyl-2-[[(2S)-3-methyl-1-methylsulfonyloxybutan-2-yl]carbamoyl]butanoyl]amino]-3-methylbutyl] methanesulfonate
• CAS: 169769-07-7
• 化学式: C₁₉H₃₈N₂O₈S₂
• 分子量: 486.651
• InChiKey: HUPVTTZLXXUXOB-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-Bis<(1S)-1-(hydroxymethyl)-2-methylpropyl>-2,2-diethyl-1,3-propanediamide bismesylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (4S,4′S)-(-)-2,2′-(3-戊烯基)双(4-异丙基噁唑啉)
  参考文献：
  名称：

  Preparation of Chiral Bisoxazolines: Observations on the Effect of Substituents

  摘要：

  A series of enantiomerically pure 4-substituted bisoxazolines 1a-f, 2c, and 2e was prepared from naturally derived or synthetic amino alcohols and malonyl dichloride derivatives. The formation of the bisoxazolines was accomplished in two stages: (1) preparation of the bis-amides of the malonyl derivatives with the amino alcohols and (2) cyclization of the hydroxy amides 4 by either of two general protocols; (1) heating with thionyl chloride in toluene or (2) formation of the bismesylate and then heating with aqueous or alcoholic base. The latter procedure was found to be more reliable especially for bisoxazolines with bulky substitutents at C(4). The C(4) trityl-substituted hydroxy amide 4f produced the bis(acylaziridine) 10 by cyclization on the nitrogen atom using KOH/MeOH, but afforded the desired bisoxazoline If by the action of SOCl2/Et(3)N. The synthesis of the nonnaturally derived amino alcohols using the Evans asymmetric azidation procedure is also described.

  DOI：

  10.1021/jo00120a036
• 作为产物：
  描述：

  二氯化二乙基丙二酰 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 N,N'-Bis<(1S)-1-(hydroxymethyl)-2-methylpropyl>-2,2-diethyl-1,3-propanediamide bismesylate
  参考文献：
  名称：

  Preparation of Chiral Bisoxazolines: Observations on the Effect of Substituents

  摘要：

  A series of enantiomerically pure 4-substituted bisoxazolines 1a-f, 2c, and 2e was prepared from naturally derived or synthetic amino alcohols and malonyl dichloride derivatives. The formation of the bisoxazolines was accomplished in two stages: (1) preparation of the bis-amides of the malonyl derivatives with the amino alcohols and (2) cyclization of the hydroxy amides 4 by either of two general protocols; (1) heating with thionyl chloride in toluene or (2) formation of the bismesylate and then heating with aqueous or alcoholic base. The latter procedure was found to be more reliable especially for bisoxazolines with bulky substitutents at C(4). The C(4) trityl-substituted hydroxy amide 4f produced the bis(acylaziridine) 10 by cyclization on the nitrogen atom using KOH/MeOH, but afforded the desired bisoxazoline If by the action of SOCl2/Et(3)N. The synthesis of the nonnaturally derived amino alcohols using the Evans asymmetric azidation procedure is also described.

  DOI：

  10.1021/jo00120a036

文献信息

• Preparation of Chiral Bisoxazolines: Observations on the Effect of Substituents
  作者：Scott E. Denmark、Noriyuki Nakajima、Olivier J.-C. Nicaise、Anne-Marie Faucher、James P. Edwards

  DOI：10.1021/jo00120a036

  日期：1995.7

  A series of enantiomerically pure 4-substituted bisoxazolines 1a-f, 2c, and 2e was prepared from naturally derived or synthetic amino alcohols and malonyl dichloride derivatives. The formation of the bisoxazolines was accomplished in two stages: (1) preparation of the bis-amides of the malonyl derivatives with the amino alcohols and (2) cyclization of the hydroxy amides 4 by either of two general protocols; (1) heating with thionyl chloride in toluene or (2) formation of the bismesylate and then heating with aqueous or alcoholic base. The latter procedure was found to be more reliable especially for bisoxazolines with bulky substitutents at C(4). The C(4) trityl-substituted hydroxy amide 4f produced the bis(acylaziridine) 10 by cyclization on the nitrogen atom using KOH/MeOH, but afforded the desired bisoxazoline If by the action of SOCl2/Et(3)N. The synthesis of the nonnaturally derived amino alcohols using the Evans asymmetric azidation procedure is also described.