(S)-3-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-4-hydroxymethyl-2,4-dimethyl-cyclohex-2-enone | 155818-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-4-hydroxymethyl-2,4-dimethyl-cyclohex-2-enone
• 英文别名: (4S)-3-[(E)-2-(2,2-dimethyl-1,3-dioxan-5-yl)ethenyl]-4-(hydroxymethyl)-2,4-dimethylcyclohex-2-en-1-one
• CAS: 155818-07-8
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: AUCIEUREWYYSJI-FUTAKVPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-4-hydroxymethyl-2,4-dimethyl-cyclohex-2-enone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 (+)-Cassiol
  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
• 作为产物：
  描述：

  2,2-二甲基-1,3-二恶烷-5-甲醛 在 sodium tetrahydroborate 、 oxazaborolidine derived from (R)-β-methyl-N-(p-tolylsulfonyl)tryptophan 、 四丁基氟化铵 、 碘 、 六甲基二硅氮烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 45.5h， 生成 (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：

  Demonstration of the Synthetic Power of Oxazaborolidine-Catalyzed Enantioselective Diels-Alder Reactions by Very Efficient Routes to Cassiol and Gibberellic Acid

  摘要：

  DOI：

  10.1021/ja00087a062

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.
• Demonstration of the Synthetic Power of Oxazaborolidine-Catalyzed Enantioselective Diels-Alder Reactions by Very Efficient Routes to Cassiol and Gibberellic Acid
  作者：E. J. Corey、Angel Guzman-Perez、Teck-Peng Loh

  DOI：10.1021/ja00087a062

  日期：1994.4
• 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.