(5S)-3,3'-二甲基-5-异丙基吡咯烷-2,4-二酮 | 103666-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (5S)-3,3'-二甲基-5-异丙基吡咯烷-2,4-二酮
• 英文名称: (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione
• 英文别名: (5S)-3,3-dimethyl-5-propan-2-ylpyrrolidine-2,4-dione
• CAS: 103666-67-7
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: MATSIKGLSGUFNW-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-3,3'-二甲基-5-异丙基吡咯烷-2,4-二酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (S)-N-[(1S,2S,3R)-2-Hydroxy-4-((R)-5-isopropyl-3,3-dimethyl-2,4-dioxo-pyrrolidin-1-yl)-1,3-dimethyl-4-oxo-butyl]-2-methylamino-propionamide
  参考文献：
  名称：

  Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin

  摘要：

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00533-5
• 作为产物：
  描述：

  ethyl (4S)-2,2,5-trimethyl-3-oxo-4-(phenylmethoxycarbonylamino)hexanoate 在 palladium on activated charcoal sodium tetrahydroborate 、 重铬酸吡啶 、 molecular sieve 、 氢气 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 (5S)-3,3'-二甲基-5-异丙基吡咯烷-2,4-二酮
  参考文献：
  名称：

  Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin

  摘要：

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00533-5

文献信息

• N-Acylation of amides with acid anhydrides by way of dual activation using MgBr2·OEt2
  作者：Shinji Yamada、Setsuko Yaguchi、Kaori Matsuda

  DOI：10.1016/s0040-4039(01)02208-0

  日期：2002.1

  A new practical method for the N-acylation of amides is described. Acylation of various amides with acid anhydrides in the presence of MgBr2.OEt2 gave the corresponding N-acylamides in good to moderate yields. The present method is applicable to amides that are labile to acids or bases. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin
  作者：Assunta Giordano、Carmela Della Monica、Francesco Landi、Aldo Spinella、Guido Sodano

  DOI：10.1016/s0040-4039(00)00533-5

  日期：2000.5

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.