4,4-dimethoxy-5-(1,1-dimethyl-2-propen-1-yl)-2,3,5-trichlorocyclopent-2-en-1-one | 914670-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-dimethoxy-5-(1,1-dimethyl-2-propen-1-yl)-2,3,5-trichlorocyclopent-2-en-1-one
• 英文别名: 2,3,5-trichloro-5-(1,1-dimethylprop-2-en-1-yl)-4,4-dimethoxycyclopent-2-en-1-one；2,3,5-trichloro-4,4-dimethoxy-5-(2-methylbut-3-en-2-yl)cyclopent-2-en-1-one
• CAS: 914670-56-7
• 化学式: C₁₂H₁₅Cl₃O₃
• 分子量: 313.608
• InChiKey: RBDLDLCRUNWRAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  4,4-dimethoxy-5-(1,1-dimethyl-2-propen-1-yl)-2,3,5-trichlorocyclopent-2-en-1-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 水 为溶剂， 以98%的产率得到2-(3-bromo-1,1-dimethyl-2-methoxypropyl)-2,4,5-trichlorocyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Synthesis of 2-(3-Bromo-1,1-dimethyl-2-methoxypropyl)-2,4,5-trichlorocyclopent-4-ene-1,3-dione

  摘要：

  DOI：

  10.1134/s1070428002120230
• 作为产物：
  描述：

  5,5-二甲氧基-1,2,3,4-四氯环戊二烯 、 3-methyl-2-buten-1-ol sodium salt 以 二甲基亚砜 为溶剂， 反应 10.0h， 以42%的产率得到4,4-dimethoxy-5-(1,1-dimethyl-2-propen-1-yl)-2,3,5-trichlorocyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis of 2-(3-Bromo-1,1-dimethyl-2-methoxypropyl)-2,4,5-trichlorocyclopent-4-ene-1,3-dione

  摘要：

  DOI：

  10.1134/s1070428002120230

文献信息

• 2,3,5-Trichlorocyclopent-2-enone derivatives in the Friedel–Crafts reaction with methoxybenzenes and the anticancer activity of the products
  作者：Victor A. Egorov、Fanuza A. Gimalova、Zulfiya R. Zileeva、Liana F. Zainullina、Yulia V. Vakhitova、Mansur S. Miftakhov

  DOI：10.1016/j.mencom.2019.03.019

  日期：2019.3

  The Friedel Crafts-type reaction of 5-allyl-2,3,5-trichlorocyclopent-2-enones with mono-, di- and trimethoxybenzenes affords the arene ketovinylation products with the cleavage of C-3-Cl bond in the starting trichlorocyclopentenones. The cytotoxocity of the products toward normal HEK293 cell lines and three cancer cell lines, SH-SY5Y, A549 and MCF-7, was evaluated.
• 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.
• Some Peculiarities of the Reduction of Di- and Trichlorocyclopentenones
  作者：V. A. Egorov、L. S. Khasanova、F. A. Gimalova、I. A. Zagreeva、M. S. Miftakhov

  DOI：10.1134/s1070428019010159

  日期：2019.1

  The hydrogenation of 5-allyl- and 5-(2-methylbut-3-en-2-yl)-2,3,5-trichlorocyclopentenones in methanol in the presence of 10% Pd/C is accompanied by exhaustive dechlorination with the formation of 3-propyl- and 3-(2-methylbutan-2-yl)cyclopentane-1,2,4-triones.