(2RS,4RS)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole | 358773-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2RS,4RS)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
• 英文别名: 1-[2-(4-trifluoromethylphenyl)4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole；(2RS,4RS)-Brz220；Brz220；1-[[4-Propyl-2-[4-(trifluoromethyl)phenyl]-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole
• CAS: 358773-79-2
• 化学式: C₁₆H₁₈F₃N₃O₂
• 分子量: 341.333
• InChiKey: PMDBWURYKQXVFA-UHFFFAOYSA-N

物化性质

• 沸点：
  437.8±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2RS,4RS)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole 在 silica gel 、 chiral stationary phase CHIRALPAK AS 作用下， 以 正己烷 、 乙酸乙酯 、 异丙醇 为溶剂， 生成 (2R,4R)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole 、 (2R,4S)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole 、 (2S,4R)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole 、 (2S,4S)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
  参考文献：
  名称：

  Brz220 a novel brassinosteroid biosynthesis inhibitor: stereochemical structure–activity relationship

  摘要：

  The four stereoisomers of Brz220 (2RS,4RS-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole), a novel brassinosteroid biosynthesis inhibitor. were separated by silica gel column chromatography and chiral high-performance liquid chromatography (HPLC). The absolute configuration of each stereoisomer was determined by a combination of asymmetric synthesis and NMR analysis. The effects of these stereoisomers on cress stem elongation clearly indicate that the (2S)-isomer has the greatest inhibitory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00475-5
• 作为产物：
  描述：

  2-溴-4'-(三氟甲基)苯乙酮 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 16.0h， 生成 (2RS,4RS)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
  参考文献：
  名称：

  A Specific and Potent Inhibitor of Brassinosteroid Biosynthesis Possessing a Dioxolane Ring

  摘要：

  Screening for brassinosteroid biosynthesis inhibitors was performed to find azole derivatives that induced dwarfism, to resemble brassinosteroid-deficient mutants in Arabidopsis, and which could be rescued by brassinosteroid. Through this screening experiment, propiconazole fungicide was selected as a likely inhibitor of brassinosteroid biosynthesis and, thus, propiconazole derivatives with optimized activity and selectivity were synthesized. The biological activity of these compounds was evaluated by examining cress stem elongation. Among the compounds tested, 2RS,4RS-1-[2-(4-trifluoromethylphenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (12) showed the most potent capability to retard cress stem elongation in the light. The compound-induced hypocotyl dwarfism was restored by the coapplication of 10 nM brassinolide but not by 1 muM gibberellin. These results suggest that 12 should affect brassinosteroid biosynthesis. The potency and specificity of 12 were greater than those of brassinazole, a previously reported brassinosteroid biosynthesis inhibitor.

  DOI：

  10.1021/jf011716w

文献信息

• A Specific and Potent Inhibitor of Brassinosteroid Biosynthesis Possessing a Dioxolane Ring
  作者：Katsuhiko Sekimata、Sun-Young Han、Koichi Yoneyama、Yasutomo Takeuchi、Shigeo Yoshida、Tadao Asami

  DOI：10.1021/jf011716w

  日期：2002.6.1

  Screening for brassinosteroid biosynthesis inhibitors was performed to find azole derivatives that induced dwarfism, to resemble brassinosteroid-deficient mutants in Arabidopsis, and which could be rescued by brassinosteroid. Through this screening experiment, propiconazole fungicide was selected as a likely inhibitor of brassinosteroid biosynthesis and, thus, propiconazole derivatives with optimized activity and selectivity were synthesized. The biological activity of these compounds was evaluated by examining cress stem elongation. Among the compounds tested, 2RS,4RS-1-[2-(4-trifluoromethylphenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (12) showed the most potent capability to retard cress stem elongation in the light. The compound-induced hypocotyl dwarfism was restored by the coapplication of 10 nM brassinolide but not by 1 muM gibberellin. These results suggest that 12 should affect brassinosteroid biosynthesis. The potency and specificity of 12 were greater than those of brassinazole, a previously reported brassinosteroid biosynthesis inhibitor.
• Brz220 a novel brassinosteroid biosynthesis inhibitor: stereochemical structure–activity relationship
  作者：Katsuhiko Sekimata、Jun Uzawa、Sun-Young Han、Koichi Yoneyama、Yasutomo Takeuchi、Shigeo Yoshida、Tadao Asami

  DOI：10.1016/s0957-4166(02)00475-5

  日期：2002.9

  The four stereoisomers of Brz220 (2RS,4RS-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole), a novel brassinosteroid biosynthesis inhibitor. were separated by silica gel column chromatography and chiral high-performance liquid chromatography (HPLC). The absolute configuration of each stereoisomer was determined by a combination of asymmetric synthesis and NMR analysis. The effects of these stereoisomers on cress stem elongation clearly indicate that the (2S)-isomer has the greatest inhibitory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.