2-azido-1-(4-tert-butyldimethylsulyloxyphenyl)ethan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-1-(4-tert-butyldimethylsulyloxyphenyl)ethan-1-one
• 英文别名: 2-azido-(4-tertbutyldimethyl-silyloxyphenyl)-1-ethanone；2-Azido-1-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]ethanone
• 化学式: C₁₄H₂₁N₃O₂Si
• 分子量: 291.425
• InChiKey: MWLDPBKQYYICKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-1-(4-tert-butyldimethylsulyloxyphenyl)ethan-1-one 在 palladium on activated charcoal potassium fluoride 、 sodium hydroxide 、 Daucus carota 、 硼烷 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 80.33h， 生成 地诺帕明
  参考文献：
  名称：

  Stereoselective synthesis of (R)-(−)-denopamine, (R)-(−)-tembamide and (R)-(−)-aegeline via asymmetric reduction of azidoketones by Daucus carota in aqueous medium

  摘要：

  A simple and efficient stereoselective synthesis of (R)-denopamine and other naturally occurring hydroxy amides from optically active (R)-2-azido-1-arylethanols, is described for the first time via reduction of the corresponding alpha-azidoarylketones with enzymes from Darcus Carota root, under mild and environmentally friendly conditions. The products are formed with high degrees of enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00024-1

文献信息

• Efficient Enantioselective Reduction of Ketones with <i>Daucus carota</i> Root
  作者：J. S. Yadav、S. Nanda、P. Thirupathi Reddy、A. Bhaskar Rao

  DOI：10.1021/jo010399p

  日期：2002.5.1

  active alcohols are the potential chiral building blocks for the synthesis of pharmaceutically important molecules and asymmetric chiral ligands. Hence, this biocatalytic approach is found to be the most suitable for the preparation of a wide range of chiral alcohols and gave inspiration for the development of a new biotechnological process.

  通过使用Daucus carota（根），可以有效地将各种手性酮（例如乙酰庚酮，α-叠氮基芳基酮，β-酮酸酯以及脂族无环和环状酮）新颖有效地还原为相应的光学活性仲醇，并具有中等至优异的化学收率。已经描述了在水性培养基中在极其温和和环境友好的条件下的植物细胞。这些旋光性醇中的许多是合成重要的药物分子和不对称手性配体的潜在手性结构单元。因此，发现这种生物催化方法最适合于制备多种手性醇，并为开发新的生物技术方法提供了启发。
• Enzymatic process for the preparation of optically active alcohols from ketones using tuberous root Daucus carota
  申请人：Council of Scientific and Industrial Research

  公开号：US07056540B2

  公开（公告）日：2006-06-06

  The present invention relates to an enzymatic process for the preparation of optically active chiral alcohols using tuberous root Daucus carota; particularly invention relates to an enzymatic process for the preparation of optically active alcohols by enantioselective reduction of corresponding ketones using tuberous root Daucus carota.

  本发明涉及使用胡萝卜块茎根制备光学活性手性醇的酶法过程；特别是涉及使用胡萝卜块茎根对相应酮进行对映选择性还原制备光学活性醇的酶法过程。
• Stereoselective synthesis of (R)-(−)-denopamine, (R)-(−)-tembamide and (R)-(−)-aegeline via asymmetric reduction of azidoketones by Daucus carota in aqueous medium
  作者：J.S. Yadav、P.Thirupathi Reddy、S. Nanda、A.Bhaskar Rao

  DOI：10.1016/s0957-4166(02)00024-1

  日期：2002.1

  A simple and efficient stereoselective synthesis of (R)-denopamine and other naturally occurring hydroxy amides from optically active (R)-2-azido-1-arylethanols, is described for the first time via reduction of the corresponding alpha-azidoarylketones with enzymes from Darcus Carota root, under mild and environmentally friendly conditions. The products are formed with high degrees of enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.