(1'S,3'R)-3-(3'-amino-2',2'-dimethylcyclobutyl)propan-1-ol | 252914-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'S,3'R)-3-(3'-amino-2',2'-dimethylcyclobutyl)propan-1-ol
• 英文别名: 3-[(1S,3R)-3-amino-2,2-dimethylcyclobutyl]propan-1-ol
• CAS: 252914-44-6
• 化学式: C₉H₁₉NO
• 分子量: 157.256
• InChiKey: HSPNZIAICBVRLJ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'S,3'R)-3-(3'-amino-2',2'-dimethylcyclobutyl)propan-1-ol 在 盐酸 、 溶剂黄146 、 三乙胺 、 锌 、 sodium nitrite 作用下， 以 乙醇 、 水 、 正丁醇 为溶剂， 反应 81.0h， 生成 3-((1S,3R)-3-(2-amino-6-chloro-9H-purin-9-yl)-2,2-dimethylcyclobutyl)propan-1-ol
  参考文献：
  名称：

  Synthesis and Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclobutane Ring

  摘要：

  The new carbocyclic nucleosides were prepared by constructing a guanine (compounds 3, 5) or 8-azaguanine (compounds 4, 6, and 7) base on the amino group of (1'S, 3'R)-3-(3'-amino-2', 2'-di-methylcyclobutyl) propan-1-ol (8), and their activities against a variety of viruses and tumor cell lines were determined. Only compounds 3 and 7 showed a detectable activity at subtoxic concentrations against some viruses tested.

  DOI：

  10.1002/(sici)1521-4184(199910)332:10<348::aid-ardp348>3.0.co;2-h
• 作为产物：
  描述：

  (1'S,3'R)-3-(3'-acetylamino-2',2'-dimethylcyclobutyl)propyl acetate 在 盐酸 作用下， 反应 22.0h， 以83%的产率得到(1'S,3'R)-3-(3'-amino-2',2'-dimethylcyclobutyl)propan-1-ol
  参考文献：
  名称：

  Synthesis and Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclobutane Ring

  摘要：

  The new carbocyclic nucleosides were prepared by constructing a guanine (compounds 3, 5) or 8-azaguanine (compounds 4, 6, and 7) base on the amino group of (1'S, 3'R)-3-(3'-amino-2', 2'-di-methylcyclobutyl) propan-1-ol (8), and their activities against a variety of viruses and tumor cell lines were determined. Only compounds 3 and 7 showed a detectable activity at subtoxic concentrations against some viruses tested.

  DOI：

  10.1002/(sici)1521-4184(199910)332:10<348::aid-ardp348>3.0.co;2-h

文献信息

• Synthesis of (1’S,3’R)-3-(3’-Amino-2’,2’-dimethylcyclobutyl)propan-1-ol from (-)-β-Pinene
  作者：José M. Blanco、Olga Caamaño、Franco Fernández、Generosa Gómez、Isabel Nieto

  DOI：10.1055/s-1996-4191

  日期：1996.2

  The title compound 3, a useful intermediate in the synthesis of carbocyclic analogs of nucleosides was synthesized from (-)-β-pinene (4) in seven steps: oxidation of 4 to (+)-nopinone (5); Beckmann rearrangement of the oxime-O-sulfonic acid of 5 to the bicyclic lactam 7 (a two-step procedure via oxime 6 is also described); hydrolytic ring opening of 7 to form amino acid • HCl 8; and reduction of the corresponding protected methyl ester 10 followed by deprotection. Overall yield, 67% from lactam 7.

  标题化合物 3 是合成核苷碳环类似物的有用中间体，由 (-)-δ蒎烯 (4) 经过七个步骤合成：4 氧化为 (+)-nopinone (5)；5 的肟-O-磺酸贝克曼重排为双环内酰胺 7（也描述了通过肟 6 的两步法）；7 的水解开环形成氨基酸 - HCl 8；还原相应的受保护甲酯 10，然后进行脱保护。内酰胺 7 的总收率为 67%。