{(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienyl}-methanol | 364330-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienyl}-methanol
• 英文别名: [(1S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-2-(2,2-dimethyl-1,3-dioxan-5-yl)ethenyl]-1,3-dimethylcyclohexa-2,4-dien-1-yl]methanol
• CAS: 364330-77-8
• 化学式: C₂₃H₄₀O₄Si
• 分子量: 408.654
• InChiKey: MRJTXWCYYZCBHA-BREAQWACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienyl}-methanol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以73%的产率得到(S)-3-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-4-hydroxymethyl-2,4-dimethyl-cyclohex-2-enone
  参考文献：
  名称：

  Detours en route to a total synthesis of (+)-cassiol

  摘要：

  A synthesis of the antiulcerogenic compound (+)-cassiol 1b has been achieved in 43% yield starting with lactol (S)-2 and sulfone 26. This short and efficient synthesis features the one-pot Julia olefination reaction of the sodium anion of (S)-2 with 26, through the key intermediate (-)-9. This synthesis has been developed as a result of exploratory experiments including different olefination reactions on 2. An attempt to synthesize the intermediate 9 by an intramolecular aldol condensation approach of the open chain precursor 4 is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00082-x
• 作为产物：
  描述：

  2-(2,2-dimethyl-[1,3]dioxan-5-ylmethanesulfonyl)-benzothiazole 在 sodium hydride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 {(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienyl}-methanol
  参考文献：
  名称：

  A concise synthesis of (+)-cassiol

  摘要：

  A synthesis of the anti-ulcerogenic compound (+)-cassiol 1b with 43% overall yield has been achieved. This short and efficient synthesis features the one-pot Julia olefination reaction of lactol (S)-2 with sulfone 3b through the key intermediate (-)-4b. (C) 2001 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00222-1