[2,2-Bis(hydroxymethyl)-3-methylidenecyclopropyl]methanol | 1021306-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2,2-Bis(hydroxymethyl)-3-methylidenecyclopropyl]methanol
• 英文别名: [2,2-bis(hydroxymethyl)-3-methylidenecyclopropyl]methanol
• CAS: 1021306-21-7
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: KWNYCKVJYSVLNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2,2-Bis(hydroxymethyl)-3-methylidenecyclopropyl]methanol 、 乙酸酐 在 吡啶 作用下， 反应 7.0h， 以2.96 g的产率得到1,1,2-三(乙酰氧基甲基)-3-亚甲基环丙烷
  参考文献：
  名称：

  Synthesis Of 2,2,3-Tris(Hydroxymethyl)Methylenecyclopropane Analogues Of Nucleosides

  摘要：

  Synthesis of 2,2,3-tris(hydroxymethyl)methylenecyclopropane analogues 16a, 16b, 17a, and 17b is described. Diethyl ester of Feist's acid 18b was hydroxymethylated via carbanion formation using formaldehyde under simultaneous isomerization to cis diester to give intermediate 19. Reduction followed by acetylation gave triacetate 22. Addition of bromine afforded reagent 23, which was used for alkylation-elimination of adenine and 2-amino-6-chloropurine to provide Z,E-isomeric mixtures of 24a and 24b. Deacetylation and separation furnished the Z-isomers 16a, 16c and E-isomers 17a, 17c. Hydrolytic dechlorination of 16c and 17c gave guanine analogues 16b and 17b. None of the analogues exhibited a significant antiviral activity. Adenosine deaminase is refractory toward adenine analogues 16a and 17a.

  DOI：

  10.1080/15257770701297000
• 作为产物：
  描述：

  diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate 在 lithium aluminium tetrahydride 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.17h， 生成 [2,2-Bis(hydroxymethyl)-3-methylidenecyclopropyl]methanol
  参考文献：
  名称：

  Synthesis Of 2,2,3-Tris(Hydroxymethyl)Methylenecyclopropane Analogues Of Nucleosides

  摘要：

  Synthesis of 2,2,3-tris(hydroxymethyl)methylenecyclopropane analogues 16a, 16b, 17a, and 17b is described. Diethyl ester of Feist's acid 18b was hydroxymethylated via carbanion formation using formaldehyde under simultaneous isomerization to cis diester to give intermediate 19. Reduction followed by acetylation gave triacetate 22. Addition of bromine afforded reagent 23, which was used for alkylation-elimination of adenine and 2-amino-6-chloropurine to provide Z,E-isomeric mixtures of 24a and 24b. Deacetylation and separation furnished the Z-isomers 16a, 16c and E-isomers 17a, 17c. Hydrolytic dechlorination of 16c and 17c gave guanine analogues 16b and 17b. None of the analogues exhibited a significant antiviral activity. Adenosine deaminase is refractory toward adenine analogues 16a and 17a.

  DOI：

  10.1080/15257770701297000

文献信息

• Synthesis Of 2,2,3-Tris(Hydroxymethyl)Methylenecyclopropane Analogues Of Nucleosides
  作者：Shaoman Zhou、Jiri Zemlicka

  DOI：10.1080/15257770701297000

  日期：2007.4.24

  Synthesis of 2,2,3-tris(hydroxymethyl)methylenecyclopropane analogues 16a, 16b, 17a, and 17b is described. Diethyl ester of Feist's acid 18b was hydroxymethylated via carbanion formation using formaldehyde under simultaneous isomerization to cis diester to give intermediate 19. Reduction followed by acetylation gave triacetate 22. Addition of bromine afforded reagent 23, which was used for alkylation-elimination of adenine and 2-amino-6-chloropurine to provide Z,E-isomeric mixtures of 24a and 24b. Deacetylation and separation furnished the Z-isomers 16a, 16c and E-isomers 17a, 17c. Hydrolytic dechlorination of 16c and 17c gave guanine analogues 16b and 17b. None of the analogues exhibited a significant antiviral activity. Adenosine deaminase is refractory toward adenine analogues 16a and 17a.