2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)undec-4-yne | 1076223-46-5

• 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: 2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)undec-4-yne
• CAS: 1076223-46-5
• 化学式: C₃₃H₅₂O₂Si₂
• 分子量: 536.946
• InChiKey: XUNRXEMJMNGYJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)undec-4-yne 在 10% Pd/C 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以95%的产率得到2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)undecane
  参考文献：
  名称：

  Spiroacetal Biosynthesis in Insects from Diptera to Hymenoptera: The Giant Ichneumon Wasp Megarhyssa nortoni nortoni Cresson

  摘要：

  The volatile components of the mandibular gland secretion generated by the Giant Ichneumon parasitoid wasp Megarhyssa nortoni nortoni Cresson are mainly spiroacetals and methyl ketones, and all have an odd number of carbon atoms. A biosynthetic scheme rationalizing the formation of these diverse components is presented. This scheme is based on the results of incorporation studies using H-2-labeled precursors and [O-18]dioxygen. The key steps are postulated to be decarboxylation of P-ketoacid equivalents, beta-oxidation (chain shortening), and monooxygenase-mediated hydroxylation leading to a putative ketodiol that cyclizes to spiroacetals. The generality of the role of monooxygenases in spiroacetal formation in insects is considered, and overall, a cohesive, internally consistent theory of spiroacetal generation by insects is presented, against which future hypotheses will have to be compared.

  DOI：

  10.1021/ja8036433
• 作为产物：
  描述：

  2-(tert-butyldimethylsilyloxy)undec-4-yn-6-ol 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 乙腈 为溶剂， 以73%的产率得到2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)undec-4-yne
  参考文献：
  名称：

  Spiroacetal Biosynthesis in Insects from Diptera to Hymenoptera: The Giant Ichneumon Wasp Megarhyssa nortoni nortoni Cresson

  摘要：

  The volatile components of the mandibular gland secretion generated by the Giant Ichneumon parasitoid wasp Megarhyssa nortoni nortoni Cresson are mainly spiroacetals and methyl ketones, and all have an odd number of carbon atoms. A biosynthetic scheme rationalizing the formation of these diverse components is presented. This scheme is based on the results of incorporation studies using H-2-labeled precursors and [O-18]dioxygen. The key steps are postulated to be decarboxylation of P-ketoacid equivalents, beta-oxidation (chain shortening), and monooxygenase-mediated hydroxylation leading to a putative ketodiol that cyclizes to spiroacetals. The generality of the role of monooxygenases in spiroacetal formation in insects is considered, and overall, a cohesive, internally consistent theory of spiroacetal generation by insects is presented, against which future hypotheses will have to be compared.

  DOI：

  10.1021/ja8036433