1,4-dimethyl-6-<(1-phenylmethyl-indol-3-yl)methyl>-3-<(3-phenylmethoxy)phenylmethylene>-(Z)-2,5-piperazinedione

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4-dimethyl-6-<(1-phenylmethyl-indol-3-yl)methyl>-3-<(3-phenylmethoxy)phenylmethylene>-(Z)-2,5-piperazinedione
• 英文别名: (6Z)-3-[(1-benzylindol-3-yl)methyl]-1,4-dimethyl-6-[(3-phenylmethoxyphenyl)methylidene]piperazine-2,5-dione
• 化学式: C₃₆H₃₃N₃O₃
• 分子量: 555.676
• InChiKey: NRJONRTZKZXYOL-HWIUFGAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(1H-indol-3-yl)-N,N,N-trimethylmethanaminium methyl sulfate 在 dilithium tetrachlorocuprate potassium tert-butylate 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,4-dimethyl-6-<(1-phenylmethyl-indol-3-yl)methyl>-3-<(3-phenylmethoxy)phenylmethylene>-(Z)-2,5-piperazinedione
  参考文献：
  名称：

  Synthetic studies on thaxtomins A and B, phytotoxins associated with Streptomyces scabies, the causal organism of potato common scab

  摘要：

  The preliminary results of a study on the stereocontrolled racemic synthesis of thaxtomins A and B are disclosed. The synthesis features a new C-C bond-forming reaction: dilithium tetrachlorocuprate was shown to be an efficient catalyst for cross-coupling reactions of lithiated 1,4-dialkyl-2,5-piperazinedione anions with gramine methosulfate and alkyl halides.

  DOI：

  10.1021/jo00065a001

文献信息

• Synthèse d'analogues structuraux de thaxtomines, phytotoxines responsables de la gale de la pomme de terre
  作者：Joël Moyroud、Jacques Gelin、Alain Chêne、Jacques Mortier

  DOI：10.1016/0040-4020(96)00408-5

  日期：1996.6

  Cross coupling reactions of lithiated 2,5-piperazinedione anions with gramine methosulfate and alkylhalides were shown to be catalyzed by copper reagents, e.g. dilithium tetrachlorocuprate and copper (I) iodide. Based on this findings, the results of the first method for preparation of racemic thaxtomins are reported. Compound 1c, chosen as a synthetic model, was prepared in five steps in 19% overall

  锂化的2,5-哌嗪二酮阴离子与氨基甲磺酸甲酯和烷基卤的交叉偶联反应显示出是由铜试剂催化的，例如四氯铜酸二锂和碘化铜（I）。基于该发现，报道了制备外消旋他克索菌素的第一种方法的结果。以五个步骤制备了被选作合成模型的化合物1c，总产率为19％。关键步骤是在催化量的四氯铜酸二锂在THF中的存在下，肌氨酸酐的锂化阴离子与氨基甲磺酸酯反应。该序列的其余部分涉及吲哚NH的保护，与3-苄氧基苯甲醛的醛醇缩合，溴代醇的形成和催化氢化。
• Synthetic studies on thaxtomins A and B, phytotoxins associated with Streptomyces scabies, the causal organism of potato common scab
  作者：Jacques Gelin、Jacques Mortier、Joel Moyroud、Alain Chene

  DOI：10.1021/jo00065a001

  日期：1993.6

  The preliminary results of a study on the stereocontrolled racemic synthesis of thaxtomins A and B are disclosed. The synthesis features a new C-C bond-forming reaction: dilithium tetrachlorocuprate was shown to be an efficient catalyst for cross-coupling reactions of lithiated 1,4-dialkyl-2,5-piperazinedione anions with gramine methosulfate and alkyl halides.