(E)-2-(5-((tert-butyldimethylsilyloxy)methyl)-1H-imidazol-1-yl)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one | 1192843-30-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-(5-((tert-butyldimethylsilyloxy)methyl)-1H-imidazol-1-yl)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one
• CAS: 1192843-30-3
• 化学式: C₂₃H₃₃ClN₂O₂Si
• 分子量: 433.066
• InChiKey: DSIONQFVMSGOAJ-DEDYPNTBSA-N

反应信息

• 作为反应物：
  描述：

  (E)-2-(5-((tert-butyldimethylsilyloxy)methyl)-1H-imidazol-1-yl)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以49%的产率得到(E)-2-(5-((tert-butyldimethylsilyloxy)methyl)-1H-imidazol-1-yl)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-ol
  参考文献：
  名称：

  Abscinazole-F1, a conformationally restricted analogue of the plant growth retardant uniconazole and an inhibitor of ABA 8′-hydroxylase CYP707A with no growth-retardant effect

  摘要：

  To develop a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, a key enzyme in the catabolism of ABA, a plant hormone involved in stress tolerance, seed dormancy, and other various physiological events, we designed and synthesized conformationally restricted analogues of uniconazole (UNI), a well-known plant growth retardant, which inhibits a biosynthetic enzyme (ent-kaurene oxidase) of gibberellin as well as ABA 8'-hydroxylase. Although most of these analogues were less effective than UNI in inhibition of ABA 8'-hydroxylase and rice seedling growth, we found that a lactol-bridged analogue with an imidazole is a potent inhibitor of ABA 8'-hydroxylase but not of plant growth. This compound, abscinazole-F1, induced drought tolerance in apple seedlings upon spray treatment with a 10 mu M solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.070
• 作为产物：
  描述：

  2-(5-((tert-butyldimethylsilyloxy)methyl)-1H-imidazol-1-yl)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one 以 乙酸乙酯 为溶剂， 反应 14.0h， 以63%的产率得到(E)-2-(5-((tert-butyldimethylsilyloxy)methyl)-1H-imidazol-1-yl)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one
  参考文献：
  名称：

  Abscinazole-F1, a conformationally restricted analogue of the plant growth retardant uniconazole and an inhibitor of ABA 8′-hydroxylase CYP707A with no growth-retardant effect

  摘要：

  To develop a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, a key enzyme in the catabolism of ABA, a plant hormone involved in stress tolerance, seed dormancy, and other various physiological events, we designed and synthesized conformationally restricted analogues of uniconazole (UNI), a well-known plant growth retardant, which inhibits a biosynthetic enzyme (ent-kaurene oxidase) of gibberellin as well as ABA 8'-hydroxylase. Although most of these analogues were less effective than UNI in inhibition of ABA 8'-hydroxylase and rice seedling growth, we found that a lactol-bridged analogue with an imidazole is a potent inhibitor of ABA 8'-hydroxylase but not of plant growth. This compound, abscinazole-F1, induced drought tolerance in apple seedlings upon spray treatment with a 10 mu M solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.070