2-[4-[2-[(Z)-hex-4-enyl]-1,3-dithian-2-yl]butoxy]oxane | 246034-85-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2-[4-[2-[(Z)-hex-4-enyl]-1,3-dithian-2-yl]butoxy]oxane
• CAS: 246034-85-5
• 化学式: C₁₉H₃₄O₂S₂
• 分子量: 358.61
• InChiKey: DBPIKGBDEOZXMD-IHWYPQMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-[2-[(Z)-hex-4-enyl]-1,3-dithian-2-yl]butoxy]oxane 在 N-氯代丁二酰亚胺 、 盐酸羟胺 、 sodium acetate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.25h， 生成 (9Z)-1-((tetrahydro-2H-pyran-2-yl)oxy)undec-9-en-5-one oxime
  参考文献：
  名称：

  Synthetic Studies on Halichlorine and Pinnaic Acid. Stereospecific Preparation of the Azaspiro Core Structure

  摘要：

  Halichlorine and pinnaic acid are two novel marine natural products isolated from a Japanese sponge and an Okinawan bivalve, respectively. The unique azaspiro[4,5]decane core structure present in both compounds provides a synthetic challenge. Herein, we describe a synthetic approach to the azaspiro[4,5]decane core structure through an intramolecular [3 + 2] cycloaddition followed by an intramolecular Michael addition and in situ isomerization to afford the azaspirocyclic core structures stereospecifically in 10 steps with 40% overall yield.

  DOI：

  10.1021/ol9907668
• 作为产物：
  描述：

  2-(4-氯丁氧基)四氢吡喃 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 9.0h， 生成 2-[4-[2-[(Z)-hex-4-enyl]-1,3-dithian-2-yl]butoxy]oxane
  参考文献：
  名称：

  Synthetic Studies on Halichlorine and Pinnaic Acid. Stereospecific Preparation of the Azaspiro Core Structure

  摘要：

  Halichlorine and pinnaic acid are two novel marine natural products isolated from a Japanese sponge and an Okinawan bivalve, respectively. The unique azaspiro[4,5]decane core structure present in both compounds provides a synthetic challenge. Herein, we describe a synthetic approach to the azaspiro[4,5]decane core structure through an intramolecular [3 + 2] cycloaddition followed by an intramolecular Michael addition and in situ isomerization to afford the azaspirocyclic core structures stereospecifically in 10 steps with 40% overall yield.

  DOI：

  10.1021/ol9907668

文献信息

• Synthetic Studies on Halichlorine and Pinnaic Acid. Stereospecific Preparation of the Azaspiro Core Structure
  作者：Sangku Lee、Zuchun (Spring) Zhao*

  DOI：10.1021/ol9907668

  日期：1999.8.1

  Halichlorine and pinnaic acid are two novel marine natural products isolated from a Japanese sponge and an Okinawan bivalve, respectively. The unique azaspiro[4,5]decane core structure present in both compounds provides a synthetic challenge. Herein, we describe a synthetic approach to the azaspiro[4,5]decane core structure through an intramolecular [3 + 2] cycloaddition followed by an intramolecular Michael addition and in situ isomerization to afford the azaspirocyclic core structures stereospecifically in 10 steps with 40% overall yield.