2-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-4-oxo-cyclohex-2-enecarboxylic acid methyl ester | 355423-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-4-oxo-cyclohex-2-enecarboxylic acid methyl ester
• 英文别名: methyl 2-[(E)-2-(2,2-dimethyl-1,3-dioxan-5-yl)ethenyl]-1,3-dimethyl-4-oxocyclohex-2-ene-1-carboxylate
• CAS: 355423-31-3
• 化学式: C₁₈H₂₆O₅
• 分子量: 322.401
• InChiKey: PGJYZFYEIDQTCL-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-4-oxo-cyclohex-2-enecarboxylic acid methyl ester 在 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 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-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)-3-(2,2-dimethyl-1,3-dioxan-5-yl)prop-2-enal 在 氢氧化钾 、 sodium hydroxide 、 重铬酸吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 2-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-4-oxo-cyclohex-2-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Studies on a New Synthetic Route towards Cassiol

  摘要：

  描述了用于制备卡西醇(2)的无环中间体7的合成。 7 的环化生成 5，即 2 的前体，并生成意想不到的产物 8。

  DOI：

  10.3390/50300505

文献信息

• Studies on a New Synthetic Route towards Cassiol
  作者：M. Colombo、J. Bacigaluppo、J. Zinczuk、M. Mischne、E. Rúveda

  DOI：10.3390/50300505

  日期：——

  The synthesis of the acyclic intermediate 7 towards the preparation of cassiol (2) is described. The cyclization of 7 led to 5, a precursor of 2 and to the unexpected product 8.

  描述了用于制备卡西醇(2)的无环中间体7的合成。 7 的环化生成 5，即 2 的前体，并生成意想不到的产物 8。
• 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.
• Detours en route to a total synthesis of (+)-cassiol
  作者：Marı́a I. Colombo、Juan Zinczuk、Marı́a L. Bohn、Edmundo A. Rúveda

  DOI：10.1016/s0957-4166(03)00082-x

  日期：2003.3

  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.