三聚氯氰与二甲亚砜促进的苄醇的选择性氯代及醚化反应
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摘要
本文报道了三聚氯氰(2,4,6-trichloro-1,3,5-triazine)与二甲亚砜(DMSO)促进的苄醇的化学选择性氯代及醚化的新方法。
本文的第一部分报道了一种苄醇的选择性氯代新方法。该方法以0.55当量的三聚氯氰作为氯代试剂,二甲亚砜作为反应溶剂,室温条件下,10-40分钟内将苄醇转化为相应的氯代产物,产率80-100%(16个例子)。该氯代反应条件温和,中性的反应条件能够与多种对酸敏感的官能团兼容,如缩醛、酯基、碳碳双键、硅醚等。大量分子内及分子间竞争实验表明,该氯代方法对于苄醇具有高度的化学选择性(8个例子)。该方法已被成功地应用于中药天麻的活性成分——天麻苷的选择性氯代。此外,我们还为这一苄醇的选择性氯代反应提出了可能的反应机理。
本文的第二部分报道了一种苄醇的化学选择性醚化新方法。该方法以1.2当量的三聚氯氰和1当量的二甲亚砜作为反应试剂,以甲醇或者乙醇作为反应溶剂,15分钟至18小时内将苄醇转化为相应的甲基或乙基苄醚,产率40-94%(12个例子)。大量分子内竞争实验表明,该方法能够在苄羟基、脂肪羟基和酚羟基同时存在下,选择性地将苄羟基转化为相应的甲基苄醚(7个例子)。该方法已被成功应用于甾体2-甲氧甲基雌二醇的制备。与文献报道的合成路线相比,新的合成路线无需保护与去保护步骤。此外,我们还为这一苄醇的选择性醚化反应提出了可能的反应机理。
总之,本文所报道的苄醇的选择性氯代及醚化新方法操作简单,试剂廉价易得,反应条件温和,为有机化学和药物化学提供了有力的工具。
Chemoselective chlorination and etherification of benzyl alcohols using TCT (2,4,6-trichloro-1,3,5-triazine) and DMSO have been reported in this dissertation.
An efficient chlorination of benzyl alcohols using 0.55 equiv of TCT in DMSO has been reported in the first part of this dissertation. Various benzyl alcohols were converted into the corresponding chlorides in the yields of 80-100% within 10 to 40 min at room temperature (16 examples). The reaction conditions are mild and compatible with substrates bearing acid-labile founctional groups, such as acetal, ester, olefin and silyl ether. Both competitive intramolecular and intermolecular reactions for benzyl alcohols in the presence of aliphatic alcohols indicate high selectivity (8 examples). The procedure has been successfully used in the selective chlorination of gastrodin, the active ingredient of Tianma. Furthermore, a possible mechanism for the selective chlorination of benzyl alcohols is proposed.
An efficient transformation of benzyl alcohols into their methyl or ethyl ethers using 1.2 equiv of TCT and 1 equiv of DMSO in methanol or ethanol has been reported in the second part of this dissertation. Benzyl alcohols were transformed into their methyl or ethyl ethers in the yields of 40-94% within 15 min to 18 h (12 examples). Competitive intramolecular reactions indicate that the etherification is chemoselective for benzylic hydroxyls in the presence of aliphatic and phenolic hydroxyls (7 examples). This procedure has been successfully used in the synthesis of 2-methoxymethylestradiol. Compared with the current synthetic route, the new route is shortened, without protection and deprotection steps. Moreover, a plausible mechanism for the selective etherification of benzyl alcohols is proposed.
In conclusion, the chemoselective chlorination and etherification of benzyl alcohols reported herein are operationally simple, and require inexpensive and commercially available reagents, which represent new useful tools in organic and medicinal chemistry.
本文的第一部分报道了一种苄醇的选择性氯代新方法。该方法以0.55当量的三聚氯氰作为氯代试剂,二甲亚砜作为反应溶剂,室温条件下,10-40分钟内将苄醇转化为相应的氯代产物,产率80-100%(16个例子)。该氯代反应条件温和,中性的反应条件能够与多种对酸敏感的官能团兼容,如缩醛、酯基、碳碳双键、硅醚等。大量分子内及分子间竞争实验表明,该氯代方法对于苄醇具有高度的化学选择性(8个例子)。该方法已被成功地应用于中药天麻的活性成分——天麻苷的选择性氯代。此外,我们还为这一苄醇的选择性氯代反应提出了可能的反应机理。
本文的第二部分报道了一种苄醇的化学选择性醚化新方法。该方法以1.2当量的三聚氯氰和1当量的二甲亚砜作为反应试剂,以甲醇或者乙醇作为反应溶剂,15分钟至18小时内将苄醇转化为相应的甲基或乙基苄醚,产率40-94%(12个例子)。大量分子内竞争实验表明,该方法能够在苄羟基、脂肪羟基和酚羟基同时存在下,选择性地将苄羟基转化为相应的甲基苄醚(7个例子)。该方法已被成功应用于甾体2-甲氧甲基雌二醇的制备。与文献报道的合成路线相比,新的合成路线无需保护与去保护步骤。此外,我们还为这一苄醇的选择性醚化反应提出了可能的反应机理。
总之,本文所报道的苄醇的选择性氯代及醚化新方法操作简单,试剂廉价易得,反应条件温和,为有机化学和药物化学提供了有力的工具。
Chemoselective chlorination and etherification of benzyl alcohols using TCT (2,4,6-trichloro-1,3,5-triazine) and DMSO have been reported in this dissertation.
An efficient chlorination of benzyl alcohols using 0.55 equiv of TCT in DMSO has been reported in the first part of this dissertation. Various benzyl alcohols were converted into the corresponding chlorides in the yields of 80-100% within 10 to 40 min at room temperature (16 examples). The reaction conditions are mild and compatible with substrates bearing acid-labile founctional groups, such as acetal, ester, olefin and silyl ether. Both competitive intramolecular and intermolecular reactions for benzyl alcohols in the presence of aliphatic alcohols indicate high selectivity (8 examples). The procedure has been successfully used in the selective chlorination of gastrodin, the active ingredient of Tianma. Furthermore, a possible mechanism for the selective chlorination of benzyl alcohols is proposed.
An efficient transformation of benzyl alcohols into their methyl or ethyl ethers using 1.2 equiv of TCT and 1 equiv of DMSO in methanol or ethanol has been reported in the second part of this dissertation. Benzyl alcohols were transformed into their methyl or ethyl ethers in the yields of 40-94% within 15 min to 18 h (12 examples). Competitive intramolecular reactions indicate that the etherification is chemoselective for benzylic hydroxyls in the presence of aliphatic and phenolic hydroxyls (7 examples). This procedure has been successfully used in the synthesis of 2-methoxymethylestradiol. Compared with the current synthetic route, the new route is shortened, without protection and deprotection steps. Moreover, a plausible mechanism for the selective etherification of benzyl alcohols is proposed.
In conclusion, the chemoselective chlorination and etherification of benzyl alcohols reported herein are operationally simple, and require inexpensive and commercially available reagents, which represent new useful tools in organic and medicinal chemistry.
引文
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