(12S,15S)-12,15-Diisobutyl-4,7-dimethyl-1,4,7,10,13-pentaaza-bicyclo[11.2.2]heptadecane-2,5,8,11,14-pentaone | 177980-70-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (12S,15S)-12,15-Diisobutyl-4,7-dimethyl-1,4,7,10,13-pentaaza-bicyclo[11.2.2]heptadecane-2,5,8,11,14-pentaone
• 英文别名: (12S,15S)-4,7-dimethyl-12,15-bis(2-methylpropyl)-1,4,7,10,13-pentazabicyclo[11.2.2]heptadecane-2,5,8,11,14-pentone
• CAS: 177980-70-0
• 化学式: C₂₂H₃₇N₅O₅
• 分子量: 451.566
• InChiKey: CZRUOZQQAKSION-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (12S,15S)-12,15-Diisobutyl-4,7-dimethyl-1,4,7,10,13-pentaaza-bicyclo[11.2.2]heptadecane-2,5,8,11,14-pentaone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以37%的产率得到(2S,14S)-2,14-Diisobutyl-7,10-dimethyl-1,4,7,10,13-pentaaza-bicyclo[11.2.2]heptadecane
  参考文献：
  名称：

  Synthesis of Structurally Reinforced Chiral Macrocyclic Polyamines and Their Metal Complexes

  摘要：

  Two structurally reinforced chiral 15-membered azamacrocycles (2S, 14S)-2,14-diisobutyl-10-methyl-1,4,7,10,13-pentaazabicydo[11.2.2]heptadecane and (2S,14S)-2,14-diisobutyl-7,10-dimethyl-1,4,7,10,13- pentaazabicyclo[11.2.2] heptadecane as a new type of ligand were conveniently synthesized by LiAlH4 reduction from their corresponding macrocyclic pseudopeptides cyclo[(2S,3'S)-2-(3'-isobutyl-2' -oxopiperazine-1'-yl)-4-methyl-pentanoyl-glycyl-glycyl-sarcosyl] and cyclo[(2S,3'S)-2-(3'-isobutyl-2'-oxopiperazine-1'-yl)-4-methyl-pentanoyl-glycyl-sarcosyl-sarcosyl], respectively. Their copper(II) complexes were also prepared and characterized.

  DOI：

  10.1080/10587259608039364
• 作为产物：
  描述：

  ethyl (2S,3'S) 2-<3'-isobutyl-2'-oxopiperazin-1'-yl>-4-methylpentanoate 在 吡啶 、 盐酸 、 sodium hydroxide 、 水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 2,3-二脱氧胞啶 作用下， 以 二氯甲烷 为溶剂， 生成 (12S,15S)-12,15-Diisobutyl-4,7-dimethyl-1,4,7,10,13-pentaaza-bicyclo[11.2.2]heptadecane-2,5,8,11,14-pentaone
  参考文献：
  名称：

  Synthesis of Structurally Reinforced Chiral Macrocyclic Polyamines and Their Metal Complexes

  摘要：

  Two structurally reinforced chiral 15-membered azamacrocycles (2S, 14S)-2,14-diisobutyl-10-methyl-1,4,7,10,13-pentaazabicydo[11.2.2]heptadecane and (2S,14S)-2,14-diisobutyl-7,10-dimethyl-1,4,7,10,13- pentaazabicyclo[11.2.2] heptadecane as a new type of ligand were conveniently synthesized by LiAlH4 reduction from their corresponding macrocyclic pseudopeptides cyclo[(2S,3'S)-2-(3'-isobutyl-2' -oxopiperazine-1'-yl)-4-methyl-pentanoyl-glycyl-glycyl-sarcosyl] and cyclo[(2S,3'S)-2-(3'-isobutyl-2'-oxopiperazine-1'-yl)-4-methyl-pentanoyl-glycyl-sarcosyl-sarcosyl], respectively. Their copper(II) complexes were also prepared and characterized.

  DOI：

  10.1080/10587259608039364

文献信息

• Structurally Reinforced Chiral Macrocyclic Polyamine Copper (II) Complexes as Studied by ESR and Squid Measurements
  作者：Naoko Yoshiki、Yoshio Seki、Hiroyuki Miyake、Yoshitane Kojima、Kazunobu Sato、Daisuke Shiomi、Takeji Takui、Koichi Itoh

  DOI：10.1080/10587259608033680

  日期：1996.3

  We have synthesized structurally reinforced chiral pentaaza-fifteen-membered polyamines 1 and 2 with a dibridge for the purposes of studying the size-match selectivity of the macrocyclic cavity. Particularly, an attempt has been made to synthesize copper(II) complexes of 1 and 2 to characterize the size-match selectivity of the polyamines in term of microscopic details of the metal-ion binding site. For this purpose the use of ESR spectroscopy has been invoked before X-ray structural analyses of the complexes are carried out. Powder-pattern ESR spectra of the copper(II) complex of 1 in crystalline solid have revealed a temperature dependence of the copper hyperfine structure. This finding suggests that a vibronic effect features in the hyperfine spectra, showing that the pentaaza-macrocycle under study accommodates copper(II) ion and the macrocycle is flexible to exert ''genuine'' size-match selectivity.
• Synthesis of Structurally Reinforced Chiral Macrocyclic Polyamines and Their Metal Complexes
  作者：Naoko Yoshiki、Yoshio Seki、Hiroyuki Miyakel、Yoshitane Kojima、Mayumi Doi、Shigenobu Yano

  DOI：10.1080/10587259608039364

  日期：1996.2

  Two structurally reinforced chiral 15-membered azamacrocycles (2S, 14S)-2,14-diisobutyl-10-methyl-1,4,7,10,13-pentaazabicydo[11.2.2]heptadecane and (2S,14S)-2,14-diisobutyl-7,10-dimethyl-1,4,7,10,13- pentaazabicyclo[11.2.2] heptadecane as a new type of ligand were conveniently synthesized by LiAlH4 reduction from their corresponding macrocyclic pseudopeptides cyclo[(2S,3'S)-2-(3'-isobutyl-2' -oxopiperazine-1'-yl)-4-methyl-pentanoyl-glycyl-glycyl-sarcosyl] and cyclo[(2S,3'S)-2-(3'-isobutyl-2'-oxopiperazine-1'-yl)-4-methyl-pentanoyl-glycyl-sarcosyl-sarcosyl], respectively. Their copper(II) complexes were also prepared and characterized.