2,3-dimethoxy-2-cyclopent-1-one | 76886-08-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 2,3-dimethoxy-2-cyclopent-1-one
• 英文别名: 2,3-dimethoxy-2-cyclopentenone；2,3-dimethoxy-cyclopent-2-enone；2,3-Dimethoxy-cyclopent-2-enon；2,3-Dimethoxycyclopent-2-en-1-one
• CAS: 76886-08-3
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: DGDADQVRKKLSRG-UHFFFAOYSA-N

物化性质

• 沸点：
  291.1±40.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-2-cyclopent-1-one 、 (1R,6S,7S)-1-Bromo-7-vinyl-bicyclo[4.1.0]heptane 在 叔丁基锂 作用下， 生成 2,3-Dimethoxy-1-((1S,6R,7R)-7-vinyl-bicyclo[4.1.0]hept-1-yl)-cyclopent-2-enol
  参考文献：
  名称：

  通过二乙烯基环丙烷重排的方法来制备底苯二酚，瑞风烷和金刚烷

  摘要：

  二乙烯基环丙烷重排已显示在天然产物的蒂利亚尼、,烷和，基烷族的骨架的构建中具有相当大的潜力。

  DOI：

  10.1016/0040-4039(80)80003-7
• 作为产物：
  描述：

  3-bromo-2-hydroxycyclopent-2-en-1-one 在 sodium methylate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 2,3-dimethoxy-2-cyclopent-1-one
  参考文献：
  名称：

  Total Synthesis of Dimethyl Glolosiphone Aviaα-Carbonyl Radical Spiro-Cyclization

  摘要：

  AbstractA general approach toward spiro[4.4]nonane structure based on the α‐carbonyl radical cyclization has been developed. Efficient total synthesis of dimethyl gloiosiphone A (2) was achieved. Thus, alkylation of the anion of dimethylhydrazone of cyclopentanone with 5‐iodopent‐1‐yne followed by hydrolysis gave ketone 4. Iodination of 4 via its TMS‐enol ether yielded iodo ketone 7. Radical spiro‐cyclization of 7 gave spiro ketone 10. Iodination of 10 afford iodo spiro ketone 23. Oxidation and iodination of 23 gave compound 24. Methylation of 24 furnished methoxy iodo enone 25. Substitution of iodide in 25 with methoxide produced dimethoxy enone 26. Allylic oxidation of 26 gave diketone 27. Treatment of 27 with OsO4 and N‐methylmorpholine N‐oxide gave dihydroxy ketone 28. Methylation of the primary alcohol group in 28 afforded dimethyl gloiosiphone A (2).

  DOI：

  10.1002/jccs.199900064

文献信息

• REMEDIES OR PREVENTIVES CONTAINING CYCLOPENTENONE COMPOUNDS AS THE ACTIVE INGREDIENT
  申请人：Takara Shuzo Co, Ltd.

  公开号：EP1112742A1

  公开（公告）日：2001-07-04

  Remedies or preventives for diseases with a need for immunoregulation, diseases with a need for inhibition of inflammation, diseases with a need for regulation of tumor necrosis factor production, diseases with a need for regulation of fungal growth, diseases with a need for regulation of cell adhesion or disease with a deed for induction of heat-shock protein, which contain as the active ingredient at least one compound selected from among cyclopentenone derivatives represented by general formula [I], optically active isomers and salts thereof, wherein R1 and R2 are the same or different and each represents hydrogen, an aliphatic group, an aromatic group or an aromatic aliphatic group.

  用于治疗或预防需要免疫调节的疾病、需要抑制炎症的疾病、需要调节肿瘤坏死因子生成的疾病、需要调节真菌生长的疾病、需要调节细胞粘附性的疾病或需要诱导热休克蛋白的疾病、其中至少含有一种选自通式[I]代表的环戊烯酮衍生物、光学活性异构体及其盐类中的化合物作为活性成分，其中 R1 和 R2 相同或不同，各自代表氢、脂肪族基团、芳香族基团或芳香族脂肪族基团。
• Hesse; Mix, Chemische Berichte, 1959, vol. 92, p. 2427,2431
  作者：Hesse、Mix

  DOI：——

  日期：——
• Reduktinsäure, ein stark reduzierendes Abbauprodukt aus Kohlehydraten. II. Mitteilung
  作者：T. Reichstein、R. Oppenauer

  DOI：10.1002/hlca.19340170145

  日期：——
• US6548543B1
  申请人：——

  公开号：US6548543B1

  公开（公告）日：2003-04-15
• Total Synthesis of Dimethyl Glolosiphone A<i>via</i>α-Carbonyl Radical Spiro-Cyclization
  作者：Chin-Kang Sha、Wen-Yueh Ho

  DOI：10.1002/jccs.199900064

  日期：1999.6

  AbstractA general approach toward spiro[4.4]nonane structure based on the α‐carbonyl radical cyclization has been developed. Efficient total synthesis of dimethyl gloiosiphone A (2) was achieved. Thus, alkylation of the anion of dimethylhydrazone of cyclopentanone with 5‐iodopent‐1‐yne followed by hydrolysis gave ketone 4. Iodination of 4 via its TMS‐enol ether yielded iodo ketone 7. Radical spiro‐cyclization of 7 gave spiro ketone 10. Iodination of 10 afford iodo spiro ketone 23. Oxidation and iodination of 23 gave compound 24. Methylation of 24 furnished methoxy iodo enone 25. Substitution of iodide in 25 with methoxide produced dimethoxy enone 26. Allylic oxidation of 26 gave diketone 27. Treatment of 27 with OsO4 and N‐methylmorpholine N‐oxide gave dihydroxy ketone 28. Methylation of the primary alcohol group in 28 afforded dimethyl gloiosiphone A (2).