(6R,7aR,12aR,3Z)-1-[[2-(trimethylsilyl)ethoxy]methyl]-3-[(1-carboxylic acid)imidazole-2-ylmetHylene]-6,12-(tert-butyldimethylsiloxy)-7a-(1,1-dimethyl-2-propenyl)-6,7,7a,12-tetrahydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5-(3H)-dione | 1450816-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (6R,7aR,12aR,3Z)-1-[[2-(trimethylsilyl)ethoxy]methyl]-3-[(1-carboxylic acid)imidazole-2-ylmetHylene]-6,12-(tert-butyldimethylsiloxy)-7a-(1,1-dimethyl-2-propenyl)-6,7,7a,12-tetrahydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5-(3H)-dione
• 英文别名: tert-butyl 4-[(Z)-[(1R,9R,11R)-2,11-bis[[tert-butyl(dimethyl)silyl]oxy]-9-(2-methylbut-3-en-2-yl)-12,15-dioxo-16-(2-trimethylsilylethoxymethyl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7-trien-14-ylidene]methyl]imidazole-1-carboxylate
• CAS: 1450816-06-4
• 化学式: C₄₅H₇₃N₅O₇Si₃
• 分子量: 880.36
• InChiKey: WRNDEEBDLJZEPH-QDWAFUFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.35
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (6R,7aR,12aR,3Z)-1-[[2-(trimethylsilyl)ethoxy]methyl]-3-[(1-carboxylic acid)imidazole-2-ylmetHylene]-6,12-(tert-butyldimethylsiloxy)-7a-(1,1-dimethyl-2-propenyl)-6,7,7a,12-tetrahydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5-(3H)-dione 在 四丁基氟化铵 、 三甲基铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.58h， 生成 (6S,7aR,12aS,3Z)-3-[1H-imidazole-2-yl-metylene]-6-(tert-butyldimethylsiloxy)-7a-(1,1-dimethyl-2-propenyl)-12-methoxy-6,7,7a,12-tetrahydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione
  参考文献：
  名称：

  Asymmetric Total Synthesis of Neoxaline

  摘要：

  A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.

  DOI：

  10.1021/ja406657v
• 作为产物：
  描述：

  (6R,7aR,12aR)-1-[[2-(trimethylsilyl)ethoxy]methyl]-6,12-(tert-butyldimethylsiloxy)-7a-(1,1-dimethyl-2-propenyl)-6,7,7a,12-tetraheydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 copper dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.48h， 生成 (6R,7aR,12aR,3Z)-1-[[2-(trimethylsilyl)ethoxy]methyl]-3-[(1-carboxylic acid)imidazole-2-ylmetHylene]-6,12-(tert-butyldimethylsiloxy)-7a-(1,1-dimethyl-2-propenyl)-6,7,7a,12-tetrahydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5-(3H)-dione
  参考文献：
  名称：

  Asymmetric Total Synthesis of Neoxaline

  摘要：

  A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.

  DOI：

  10.1021/ja406657v