N-[2,4-dichloro-4-(1,1-dimethylprop-2-en-1-yl)-5,5-dimethoxy-3-oxocyclopent-1-en-1-yl]-D-leucine methyl ester | 1307825-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2,4-dichloro-4-(1,1-dimethylprop-2-en-1-yl)-5,5-dimethoxy-3-oxocyclopent-1-en-1-yl]-D-leucine methyl ester
• 英文别名: N-[2,4-dichloro-4-(1,1-dimethylprop-2-en-1-yl)-5,5-dimethoxy-3-oxocyclopent-1-en-1-yl]-d-leucine methyl ester；methyl (2R)-2-[[2,4-dichloro-5,5-dimethoxy-4-(2-methylbut-3-en-2-yl)-3-oxocyclopenten-1-yl]amino]-4-methylpentanoate
• CAS: 1307825-04-2
• 化学式: C₁₉H₂₉Cl₂NO₅
• 分子量: 422.349
• InChiKey: FGRHZTOWDKFCMJ-GKOGFXNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4-dimethoxy-5-(1,1-dimethyl-2-propen-1-yl)-2,3,5-trichlorocyclopent-2-en-1-one 、 (R)-leucine methyl ester hydrochloride 在 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以54%的产率得到N-[2,4-dichloro-4-(1,1-dimethylprop-2-en-1-yl)-5,5-dimethoxy-3-oxocyclopent-1-en-1-yl]-D-leucine methyl ester
  参考文献：
  名称：

  New nitrogen- and sulfur-containing derivatives of chlorocyclopentenones

  摘要：

  Reactions of 2,3,5-trichloro-4,4-ethylenedioxy- and 2,3,5-trichloro-5-(1,1-dimethylprop-2-en-1-yl)-4,4-dimethoxycyclopent-2-en-1-ones with amino acids gave products of Ad(N)E substitution at the C-3 atom, the corresponding vinylogous amides. Sodium carbamodithioates generated in situ from amines, carbon disulfide, and sodium hydride in tetrahydrofuran reacted with di- and trichlorocyclopentenones in a similar way. Cyanosilylation of 2,3,5-trichloro-4,4-ethylenedioxyyclopent-2-en-1-one with trimethylsilyl cyanide smoothly occurred in toluene at 25 degrees C in the presence of glycine as catalyst.

  DOI：

  10.1134/s1070428011030067

文献信息

• New nitrogen- and sulfur-containing derivatives of chlorocyclopentenones
  作者：V. A. Egorov、G. M. Khalikova、F. A. Gimalova、A. V. Grachev、M. S. Miftakhov

  DOI：10.1134/s1070428011030067

  日期：2011.3

  Reactions of 2,3,5-trichloro-4,4-ethylenedioxy- and 2,3,5-trichloro-5-(1,1-dimethylprop-2-en-1-yl)-4,4-dimethoxycyclopent-2-en-1-ones with amino acids gave products of Ad(N)E substitution at the C-3 atom, the corresponding vinylogous amides. Sodium carbamodithioates generated in situ from amines, carbon disulfide, and sodium hydride in tetrahydrofuran reacted with di- and trichlorocyclopentenones in a similar way. Cyanosilylation of 2,3,5-trichloro-4,4-ethylenedioxyyclopent-2-en-1-one with trimethylsilyl cyanide smoothly occurred in toluene at 25 degrees C in the presence of glycine as catalyst.