(2E,4E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-deca-2,4-dienal | 185749-13-7

• 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: (2E,4E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-deca-2,4-dienal
• 英文别名: (2E,4E,9S)-9-[tert-butyl(diphenyl)silyl]oxydeca-2,4-dienal
• CAS: 185749-13-7
• 化学式: C₂₆H₃₄O₂Si
• 分子量: 406.64
• InChiKey: MAMFBOXJXOHCEB-CEYCQPKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]ethenolate;tin(2+);trifluoromethanesulfonate 、 (2E,4E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-deca-2,4-dienal 以 二氯甲烷 为溶剂， 反应 0.33h， 以78%的产率得到(4E,6E)-(3R,11S)-11-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-dodeca-4,6-dien-1-one
  参考文献：
  名称：

  Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

  摘要：

  Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02055-2
• 作为产物：
  描述：

  (2E,4E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-deca-2,4-dien-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以95%的产率得到(2E,4E)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-deca-2,4-dienal
  参考文献：
  名称：

  Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

  摘要：

  Asymmetric aldol-like reactions of cinnamaldehyde, dienal 3 (fragment C7-C12 of macrolactin A), and dienal 4 (fragment C15-C24) with (i) chiral acetylthiazolidinethione-derived enolates, (ii) chiral boron enolates, and (iii) silyl enolates in the presence of chiral titanium-2,2'-dinaphthol complexes are compared. Use of the thiazolidinethione auxiliary and TiCl4 shows practical advantages; e.g., C5-C12 fragment 7 has been isolated enantiomerically pure in 74% yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02055-2