(1R,4S)-1-azido-4-(2'-furyl)-2-cyclopentene | 225226-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1R,4S)-1-azido-4-(2'-furyl)-2-cyclopentene
• 英文别名: 2-[(1S,4R)-4-azidocyclopent-2-en-1-yl]furan
• CAS: 225226-71-1
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: PSJKMCFUNBNASF-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S)-1-azido-4-(2'-furyl)-2-cyclopentene 在 ruthenium trichloride sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 水 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 反应 7.0h， 生成 (3aS,4R,6R,6aR)-[6-(6-chloropurin-9-yl)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-4-yl]methanol
  参考文献：
  名称：

  Realisation of highly stereoselective dihydroxylation of a cyclopentene in the synthesis of (−)-aristeromycin

  摘要：

  2-呋喃基被用作阿里霉素4-位CH2OH的合成等价物，具有呋喃基的环戊烯的二羟基化高度立体选择性地进行，生成合成(α)-的关键二醇。阿里斯霉素。

  DOI：

  10.1039/a901819k
• 作为产物：
  描述：

  Lithium;2-butyl-2-(furan-2-yl)-4,5-dimethyl-1,3-dioxa-2-boranuidacyclopentane 在 bis(triphenylphosphine)nickel(II) chloride 叠氮磷酸二苯酯 作用下， 生成 (1R,4S)-1-azido-4-(2'-furyl)-2-cyclopentene
  参考文献：
  名称：

  Realisation of highly stereoselective dihydroxylation of a cyclopentene in the synthesis of (−)-aristeromycin

  摘要：

  2-呋喃基被用作阿里霉素4-位CH2OH的合成等价物，具有呋喃基的环戊烯的二羟基化高度立体选择性地进行，生成合成(α)-的关键二醇。阿里斯霉素。

  DOI：

  10.1039/a901819k

文献信息

• Highly Stereoselective Synthesis of Aristeromycin through Dihydroxylation of 4-Aryl-1-azido-2-cyclopentenes
  作者：Takauki Ainai、Yong-Gang Wang、Yuko Tokoro、Yuichi Kobayashi

  DOI：10.1021/jo034672u

  日期：2004.2.1

  Dihydroxylation of 4-aryl-1-azido-2-cyclopentenes 6, in which an aryl group is used as a synthetic equivalent of CH2OH, was studied to improve the low to moderate stereoselectivity previously reported for cyclopentenes 3 possessing CH2X and nitrogen atom-containing groups. 2-Furyl, Ph, and p-MeOC6H4 groups were chosen as the aryl groups. Compounds 6a-c possessing such aryl groups were prepared by CuCN-catalyzed reaction between 2-cyclopentene-1,4-diol monoacetate 9 and the corresponding Grignard reagents followed by substitution of the hydroxyl group with (PhO)(2)P(=O)N-3. The desired diols 7a-c were obtained with higher selectivities of > 7:1 when dihydroxylation of 6a-c was carried out at 0degreesC with OsO4 (catalyst) and NMO in a mixed solvent of MeCN, THF, t-BuOH, and H2O. Among them, the furyl compound recorded the highest selectivity of 14:1. The furyl and azido groups on diol 7a were converted into hydroymethyl and adeninyl groups, respectively, to produce acetonide 2, which upon hydrolysis affords aristeromycin 1.
• Realisation of highly stereoselective dihydroxylation of a cyclopentene in the synthesis of (−)-aristeromycin
  作者：Yuko Tokoro、Yuichi Kobayashi

  DOI：10.1039/a901819k

  日期：——

  A 2-furyl group was used as a synthetic equivalent of the CH2OH at the 4′ position of aristeromycin, and dihydroxylation of the cyclopentene possessing the furyl group proceeded highly stereoselectively to produce the key diol for the synthesis of (–)-aristeromycin.

  2-呋喃基被用作阿里霉素4-位CH2OH的合成等价物，具有呋喃基的环戊烯的二羟基化高度立体选择性地进行，生成合成(α)-的关键二醇。阿里斯霉素。