(5R)-7-[tert-butyl(dimethyl)silyl]oxy-5-methylhept-1-en-4-ol | 1024002-25-2

• 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: (5R)-7-[tert-butyl(dimethyl)silyl]oxy-5-methylhept-1-en-4-ol
• CAS: 1024002-25-2
• 化学式: C₁₄H₃₀O₂Si
• 分子量: 258.476
• InChiKey: NYLQDAGRXUYBGH-PZORYLMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (5R)-7-[tert-butyl(dimethyl)silyl]oxy-5-methylhept-1-en-4-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(5R)-7-[tert-butyl(dimethyl)silyl]oxy-5-methylhept-1-en-4-yl] acetate
  参考文献：
  名称：

  Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar

  摘要：

  The first enantioselective synthesis of (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a potent antifeedant isolated from the Japanese cedar. Cryptomeria japonica, was achieved starting from methyl (R)-4-hydroxy-3-methylbutanoate via a stereoselective carbonyl ene cyclization reaction as the key step. Comparison of the spectral data and specific rotation of the synthetic material with those of the natural product led to unambiguous stereochemical assignment of the antifeedant as 1S, 3R, and 6R. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.039
• 作为产物：
  描述：

  (R)-(-)-4-tert-butyldimethylsilyloxy-1-methylbutanal 、 烯丙基溴化镁 以 乙醚 为溶剂， 生成 (5R)-7-[tert-butyl(dimethyl)silyl]oxy-5-methylhept-1-en-4-ol
  参考文献：
  名称：

  Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar

  摘要：

  The first enantioselective synthesis of (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a potent antifeedant isolated from the Japanese cedar. Cryptomeria japonica, was achieved starting from methyl (R)-4-hydroxy-3-methylbutanoate via a stereoselective carbonyl ene cyclization reaction as the key step. Comparison of the spectral data and specific rotation of the synthetic material with those of the natural product led to unambiguous stereochemical assignment of the antifeedant as 1S, 3R, and 6R. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.039

文献信息

• Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar
  作者：Takashi Nakahata、Yohsuke Satoh、Shigefumi Kuwahara

  DOI：10.1016/j.tetlet.2008.02.039

  日期：2008.4

  The first enantioselective synthesis of (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a potent antifeedant isolated from the Japanese cedar. Cryptomeria japonica, was achieved starting from methyl (R)-4-hydroxy-3-methylbutanoate via a stereoselective carbonyl ene cyclization reaction as the key step. Comparison of the spectral data and specific rotation of the synthetic material with those of the natural product led to unambiguous stereochemical assignment of the antifeedant as 1S, 3R, and 6R. (C) 2008 Elsevier Ltd. All rights reserved.