(S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol | 1280222-59-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol
• 英文别名: (1S)-1-[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]octan-1-ol
• CAS: 1280222-59-4
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: HZLNCRBJVNJGHZ-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 喹啉 、 盐酸 、 4-二甲氨基吡啶 、 氢气 、 氟化氢吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 40.0h， 生成 (-)-mangiferaelactone
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-mangiferaelactone by using an appropriately substituted thiophene as a masked synthon for C-alkyl glycoside

  摘要：

  Asymmetric total synthesis of naturally occurring nonenolide (-)-mangiferaelactone was attempted through RCAM (ring closing alkyne metathesis) reaction. As the attempted RCAM reaction failed, the synthesis was finally achieved by successful exploration of a ring closing metathesis (RCM) reaction. 2-Propylthiophene was used as a masked synthon for n-heptyl glycoside, which served as main source for one of the RCM precursors and accessed by reductive desulfurization (Mozingo type reduction) of an appropriately substituted thiophene ribofuranoside. The other RCM precursor was accessed by applying an enzymatic kinetic resolution/Mitsunobu inversion sequence to an alkyne alcohol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.001
• 作为产物：
  描述：

  (R)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 苯甲酸 、 sodium hydroxide 作用下， 以86%的产率得到(S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-mangiferaelactone by using an appropriately substituted thiophene as a masked synthon for C-alkyl glycoside

  摘要：

  Asymmetric total synthesis of naturally occurring nonenolide (-)-mangiferaelactone was attempted through RCAM (ring closing alkyne metathesis) reaction. As the attempted RCAM reaction failed, the synthesis was finally achieved by successful exploration of a ring closing metathesis (RCM) reaction. 2-Propylthiophene was used as a masked synthon for n-heptyl glycoside, which served as main source for one of the RCM precursors and accessed by reductive desulfurization (Mozingo type reduction) of an appropriately substituted thiophene ribofuranoside. The other RCM precursor was accessed by applying an enzymatic kinetic resolution/Mitsunobu inversion sequence to an alkyne alcohol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.001

文献信息

• Stereoselective Total Synthesis of (+)-Oploxyne A, (−)-Oploxyne B, and Their C-10 Epimers and Structure Revision of Natural Oploxyne B
  作者：J. S. Yadav、Kumaraswamy Boyapelly、Sathish Reddy Alugubelli、Srihari Pabbaraja、Janakiram R Vangala、Shasi V Kalivendi

  DOI：10.1021/jo102445h

  日期：2011.4.15

  The first total synthesis of recently isolated diacetylene alcohols oploxyne A, oploxyne B, and their C-10 epimers was accomplished. The structure of natural oploxyne B has been revised. The key steps involved are base-induced double elimination of a carbohydrate-derived β-alkoxy chloride to generate the chiral acetylenic alcohol and Cadiot−Chodkiewicz cross-coupling reaction. The target compounds

  完成了最近分离的二乙炔醇oploxyne A，oploxyne B及其C-10差向异构体的第一个全合成。天然环氧烷B的结构已被修改。涉及的关键步骤是碱诱导的碳水化合物衍生的β-烷氧基氯化物的双消除，从而生成手性炔醇和Cadiot-Chodkiewicz交叉偶联反应。目标化合物显示出针对神经母细胞瘤和前列腺癌细胞系的有效细胞毒性。