(R)-9-tert-butyldimethylsilyloxy-1-decanol | 158564-01-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-9-tert-butyldimethylsilyloxy-1-decanol
• 英文别名: (9R)-9-[tert-butyl(dimethyl)silyl]oxydecan-1-ol
• CAS: 158564-01-3
• 化学式: C₁₆H₃₆O₂Si
• 分子量: 288.546
• InChiKey: AEJXEGQKGXDFTP-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-9-tert-butyldimethylsilyloxy-1-decanol 在 吡啶 、 重铬酸吡啶 、 2,2'-二硫二吡啶 、 氢氟酸 、 silver perchlorate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.0h， 生成 (R)-(-)-phoracantholide I
  参考文献：
  名称：

  Catalytic enantioselective synthesis of macrolides via asymmetric alkylation

  摘要：

  Catalytic enantioselective syntheses of the macrolides (R)-(-) phoracantholide and (R)-(+) lasiodiplodin have been achieved. Stereochemistry was introduced in using an arene chromium tricarbonyl derived catalyst, which mediated the enantioselective addition of dimethyl zinc to a functionalized aldehyde. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00186-9
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 (R)-9-tert-butyldimethylsilyloxy-1-decanol
  参考文献：
  名称：

  Catalytic enantioselective synthesis of macrolides via asymmetric alkylation

  摘要：

  Catalytic enantioselective syntheses of the macrolides (R)-(-) phoracantholide and (R)-(+) lasiodiplodin have been achieved. Stereochemistry was introduced in using an arene chromium tricarbonyl derived catalyst, which mediated the enantioselective addition of dimethyl zinc to a functionalized aldehyde. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00186-9

文献信息

• Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination
  作者：Gowravaram Sabitha、G. Chandrashekhar、K. Yadagiri、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.05.063

  日期：2010.7

  The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential alpha-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are used as the key reaction steps. (C) 2010 Elsevier Ltd. All rights reserved.
• Catalytic enantioselective synthesis of macrolides via asymmetric alkylation
  作者：Graham B. Jones、Robert S. Huber、Brant J. Chapman

  DOI：10.1016/s0957-4166(97)00186-9

  日期：1997.6

  Catalytic enantioselective syntheses of the macrolides (R)-(-) phoracantholide and (R)-(+) lasiodiplodin have been achieved. Stereochemistry was introduced in using an arene chromium tricarbonyl derived catalyst, which mediated the enantioselective addition of dimethyl zinc to a functionalized aldehyde. (C) 1997 Elsevier Science Ltd.