(3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione | 923293-48-5

• 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: (3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione
• 英文别名: (3S,6S)-3-[(4-bromophenyl)methyl]-1-[[1-[(2S)-1-hydroxy-3-phenylpropan-2-yl]triazol-4-yl]methyl]-4-(3-hydroxypropyl)-6-(phenylmethoxymethyl)piperazine-2,5-dione
• CAS: 923293-48-5
• 化学式: C₃₄H₃₈BrN₅O₅
• 分子量: 676.61
• InChiKey: YLSMBVVMXHVRQM-CPCREDONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione 、 丙烯酸甲酯（MA） 在 palladium diacetate 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以83%的产率得到(3S,6S)-3-(benzyloxymethyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)-6-(4-(2-methoxycarbonylethenyl)benzyl)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis of Functionalized, Unsymmetrical 1,3,4,6-Tetrasubstituted 2,5-Diketopiperazines

  摘要：

  A general and efficient method for the synthesis of unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketo- piperazines (DKPs) is described. Cyclization of N-amide alkylated dipeptide methyl esters, followed by alkylation, furnished the corresponding tetrasubstituted DKPs in good overall yields. The influence of steric hindrance in the alkylation reactions appeared to be of lesser importance as long as reactive alkylating agents were used. Furthermore, we have demonstrated the use of tetrasubstituted DKPs as a scaffold for further chemical manipulations to produce novel DKPs with desired properties.

  DOI：

  10.1021/jo0619635
• 作为产物：
  描述：

  Boc-L-4-溴苯丙氨酸 在 硼烷四氢呋喃络合物 、 copper(II) sulfate 、 sodium ascorbate 、 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.72h， 生成 (3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis of Functionalized, Unsymmetrical 1,3,4,6-Tetrasubstituted 2,5-Diketopiperazines

  摘要：

  A general and efficient method for the synthesis of unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketo- piperazines (DKPs) is described. Cyclization of N-amide alkylated dipeptide methyl esters, followed by alkylation, furnished the corresponding tetrasubstituted DKPs in good overall yields. The influence of steric hindrance in the alkylation reactions appeared to be of lesser importance as long as reactive alkylating agents were used. Furthermore, we have demonstrated the use of tetrasubstituted DKPs as a scaffold for further chemical manipulations to produce novel DKPs with desired properties.

  DOI：

  10.1021/jo0619635

文献信息

• Synthesis of Functionalized, Unsymmetrical 1,3,4,6-Tetrasubstituted 2,5-Diketopiperazines
  作者：Marcus Tullberg、Morten Grøtli、Kristina Luthman

  DOI：10.1021/jo0619635

  日期：2007.1.1

  A general and efficient method for the synthesis of unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketo- piperazines (DKPs) is described. Cyclization of N-amide alkylated dipeptide methyl esters, followed by alkylation, furnished the corresponding tetrasubstituted DKPs in good overall yields. The influence of steric hindrance in the alkylation reactions appeared to be of lesser importance as long as reactive alkylating agents were used. Furthermore, we have demonstrated the use of tetrasubstituted DKPs as a scaffold for further chemical manipulations to produce novel DKPs with desired properties.