| 132150-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 132150-28-8
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: CIJXSZQGAJXZPQ-PCCBWWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.94
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 氨 、 三乙胺 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 96.0h， 生成 (+/-)-9-<1,6-Di-O-benzyl-3,4-O-(ethoxymethylene)-2a,5-didehydro-2a-carba-β-psicofuranosyl>adenine
  参考文献：
  名称：

  Synthesis of (±)- psicoplanocin A.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98007-9
• 作为产物：
  描述：

  (+/-)-1,6-Di-O-benzyl-2a,5-didehydro-2a-carba-β-psicofuranosyl azide 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以99%的产率得到
  参考文献：
  名称：

  Synthesis of (±)- psicoplanocin A.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98007-9

文献信息

• Synthesis of carbocyclic analogs of 1-.beta.-D-psicofuranosyl nucleosides. psico-Cyclopentenyladenosine (psicoplanocin A) and psico-cyclopentenylcytosine
  作者：Michael Bodenteich、Victor E. Marquez、Joseph J. Barchi、Wendy H. Hallows、Barry M. Goldstein、John S. Driscoll

  DOI：10.1021/jo00074a030

  日期：1993.10

  Psicoplanocin A (4a) and psico-cyclopentenylcytosine (4b) represent the first two known examples of carbocyclic ketohexose nucleosides. These two stable compounds combine structural features of two known classes of natural products: neplanocin A and the ketohexose nucleosides psicofuranine (1a) and decoynine (2). Both compounds were synthesized in racemic form from (+/-)-cyclopentenone 5, which in turn was available froM D-ribonolactone. Construction of the surrogate glycon moiety commenced with the attachment of a protected hydroxymethyl fragment onto the ketone carbonyl of 5 via nucleophilic addition of [(benzoyloxy)methyl]lithium to give intermediate 7. Introduction of the requisite nitrogen at the tertiary allylic carbon of 7 was achieved by the BF3.OEt2-catalyzed addition of hydrazoic acid to a generated transitional allylic cation. This method produced the epimeric azides 8a and 8b, and following conversion of the beta-azide (8a) to the corresponding carbocyclic amine, the purine and pyrimidine rings of psicoplanocin A and psico-cyclopentenylcytosine were constructed by conventional methods. An X-ray crystallographic analysis corroborated the structure of psicoplanocin A determined from NOE experiments on the epimeric azides. Both psicoplanocin A and psico-cyclopentenylcytosine were found to be devoid of cell cytotoxicity and in vitro antiviral activity.