methyl 3-{[t-butyl(dimethyl)silyl]oxy}-4-(p-methoxybenzyloxy)-2-methylenebutanoate | 1222854-21-8

• 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: methyl 3-{[t-butyl(dimethyl)silyl]oxy}-4-(p-methoxybenzyloxy)-2-methylenebutanoate
• 英文别名: methyl 3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-2-methylenebutanoate；methyl (3S)-3-[tert-butyl(dimethyl)silyl]oxy-4-[(4-methoxyphenyl)methoxy]-2-methylidenebutanoate
• CAS: 1222854-21-8
• 化学式: C₂₀H₃₂O₅Si
• 分子量: 380.557
• InChiKey: CBMVLHDKMSAOBP-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-{[t-butyl(dimethyl)silyl]oxy}-4-(p-methoxybenzyloxy)-2-methylenebutanoate 在 lithium hydroxide monohydrate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (4’S,1’S)-1’-ethyloxycarbonyl-3’-phenylprop-1’-yl 3,4-bis{[t-butyl(dimethyl)silyl]oxy}-2-methylenebutanoate
  参考文献：
  名称：

  A New Template of MIitsunobu Acylate Cleavable in Non-Alkaline Conditions

  摘要：

  DOI：

  10.3987/com-21-14562
• 作为产物：
  描述：

  2-[(4-甲氧基苯基)甲氧基]乙醛 在 三乙烯二胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 methyl 3-{[t-butyl(dimethyl)silyl]oxy}-4-(p-methoxybenzyloxy)-2-methylenebutanoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of 6-Tuliposide B and Its Biological Activities against Tulip Pathogenic Fungi

  摘要：

  为评估郁金香苷和郁金香醛对郁金香致病真菌的抗真菌活性，研究了其结构-活性关系。通过不对称 Baylis-Hillman 反应，有效合成了 6-郁金香苷 B。郁金香苷和郁金香醛在高浓度（2.5 毫米）下对大多数受试菌株具有抗真菌活性，而郁金香灰霉病菌对郁金香苷具有抗性。郁金香苷的形成参与了抗真菌活性，郁金香苷 A 的抑制活性高于 6-郁金香苷 B 和郁金香苷 B。郁金香苷和郁金香醛都对 Gibberella zeae 具有色素诱导活性，对 Fusarium oxysporum f. sp tulipae 具有抑制活性。这些活性是在比抗真菌 MIC 值低得多的浓度（0.05 毫米）下产生的。

  DOI：

  10.1271/bbb.100845

文献信息

• Asymmetric Total Synthesis of 6-Tuliposide B and Its Biological Activities against Tulip Pathogenic Fungi
  作者：Kengo SHIGETOMI、Shoko OMOTO、Yasuo KATO、Makoto UBUKATA

  DOI：10.1271/bbb.100845

  日期：2011.4.23

  The structure-activity relationship was investigated to evaluate the antifungal activities of tuliposides and tulipalins against tulip pathogenic fungi. 6-Tuliposide B was effectively synthesized via the asymmetric Baylis-Hillman reaction. Tuliposides and tulipalins showed antifungal activities against most of the strains tested at high concentrations (2.5 mm), while Botrytis tulipae was resistant to tuliposides. Tulipalin formation was involved in the antifungal activity, tulipalin A showed higher inhibitory activity than 6-tuliposide B and tulipalin B. Both the tuliposides and tulipalins showed pigment-inducing activity against Gibberella zeae and inhibitory activity against Fusarium oxysporum f. sp tulipae. These activities were induced at a much lower concentration (0.05 mm) than the antifungal MIC values.

  为评估郁金香苷和郁金香醛对郁金香致病真菌的抗真菌活性，研究了其结构-活性关系。通过不对称 Baylis-Hillman 反应，有效合成了 6-郁金香苷 B。郁金香苷和郁金香醛在高浓度（2.5 毫米）下对大多数受试菌株具有抗真菌活性，而郁金香灰霉病菌对郁金香苷具有抗性。郁金香苷的形成参与了抗真菌活性，郁金香苷 A 的抑制活性高于 6-郁金香苷 B 和郁金香苷 B。郁金香苷和郁金香醛都对 Gibberella zeae 具有色素诱导活性，对 Fusarium oxysporum f. sp tulipae 具有抑制活性。这些活性是在比抗真菌 MIC 值低得多的浓度（0.05 毫米）下产生的。
• The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship
  作者：Kengo Shigetomi、Kazuaki Shoji、Shinya Mitsuhashi、Makoto Ubukata

  DOI：10.1016/j.phytochem.2009.10.008

  日期：2010.2

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.
• A New Template of MIitsunobu Acylate Cleavable in Non-Alkaline Conditions
  作者：Kengo Shigetomi、Yoshimichi Sakakibara、Yusuke Sai、Yasumitsu Uraki、Makoto Ubukata

  DOI：10.3987/com-21-14562

  日期：——