4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienecarboxylic acid methyl ester | 364330-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienecarboxylic acid methyl ester
• CAS: 364330-78-9
• 化学式: C₂₄H₄₀O₅Si
• 分子量: 436.664
• InChiKey: DOPHKQGAGBKTPQ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienecarboxylic acid methyl ester 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以85%的产率得到{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：

  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：

  (E)-5-(2,2-Dimethyl-[1,3]dioxan-5-yl)-3-hydroxy-2-methyl-pent-4-enoic acid methyl ester 在 氢氧化钾 、 sodium hydroxide 、 piridinium dichlorochromate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienecarboxylic acid methyl ester
  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

文献信息

• A concise synthesis of (+)-cassiol
  作者：Marı́a I Colombo、Juan Zinczuk、Mirta P Mischne、Edmundo A Rúveda

  DOI：10.1016/s0957-4166(01)00222-1

  日期：2001.6

  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.