[1-(t-butyldimethylsilanyloxymethyl)cyclopropyl]acetaldehyde | 1062065-95-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [1-(t-butyldimethylsilanyloxymethyl)cyclopropyl]acetaldehyde
• 英文别名: [1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopropyl]-acetaldehyde；2-[1-[[Tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]acetaldehyde；2-[1-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopropyl]acetaldehyde
• CAS: 1062065-95-5
• 化学式: C₁₂H₂₄O₂Si
• 分子量: 228.407
• InChiKey: JRGIHEMKBGJPON-UHFFFAOYSA-N

物化性质

• 沸点：
  250.6±13.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1-(t-butyldimethylsilanyloxymethyl)cyclopropyl]acetaldehyde 在 4-二甲氨基吡啶 、 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二甲基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Synthesis of Novel 2′-Spirocyclopropyl-5′- Deoxyphosphonic Acid Furanosyl Nucleoside Analogues as Potent Antiviral Agents

  摘要：

  Novel 5'-deoxyfuranosyl purine phosphonic acid analogues with 2'-electropositive moiety, such as spirocyclopropanoid, were designed and synthesized from commercially available diethyl malonate. Condensation reaction successfully proceeded from a glycosyl donor 15 at low reaction temperature in Vorbruggen conditions to give desired phosphonate analogues 16b and 23b. The synthesized nucleotide analogues 19, 22, 26, and 29 were subjected to antiviral screening against HIV-1. Adenine phosphonic acid analogue 22 shows significant anti-HIV activity (EC50 = 7.9 mu M).

  DOI：

  10.1080/15257770.2012.695839
• 作为产物：
  描述：

  [1-(叔丁基二甲基甲硅烷基氧基甲基)环丙基]甲醇 在 正丁基锂 、 硼烷四氢呋喃络合物 、 草酰氯 、 二甲基亚砜 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.16h， 生成 [1-(t-butyldimethylsilanyloxymethyl)cyclopropyl]acetaldehyde
  参考文献：
  名称：

  Synthesis of Novel 2′-Spirocyclopropyl-5′- Deoxyphosphonic Acid Furanosyl Nucleoside Analogues as Potent Antiviral Agents

  摘要：

  Novel 5'-deoxyfuranosyl purine phosphonic acid analogues with 2'-electropositive moiety, such as spirocyclopropanoid, were designed and synthesized from commercially available diethyl malonate. Condensation reaction successfully proceeded from a glycosyl donor 15 at low reaction temperature in Vorbruggen conditions to give desired phosphonate analogues 16b and 23b. The synthesized nucleotide analogues 19, 22, 26, and 29 were subjected to antiviral screening against HIV-1. Adenine phosphonic acid analogue 22 shows significant anti-HIV activity (EC50 = 7.9 mu M).

  DOI：

  10.1080/15257770.2012.695839

文献信息

• Synthesis of Novel 2′-Spirocyclopropyl-5′- Deoxyphosphonic Acid Furanosyl Nucleoside Analogues as Potent Antiviral Agents
  作者：Guang Huan Shen、Joon Hee Hong

  DOI：10.1080/15257770.2012.695839

  日期：2012.7

  Novel 5'-deoxyfuranosyl purine phosphonic acid analogues with 2'-electropositive moiety, such as spirocyclopropanoid, were designed and synthesized from commercially available diethyl malonate. Condensation reaction successfully proceeded from a glycosyl donor 15 at low reaction temperature in Vorbruggen conditions to give desired phosphonate analogues 16b and 23b. The synthesized nucleotide analogues 19, 22, 26, and 29 were subjected to antiviral screening against HIV-1. Adenine phosphonic acid analogue 22 shows significant anti-HIV activity (EC50 = 7.9 mu M).