(1S,3Z)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oct-3-en-7-yne-1,6-diol | 444885-26-1

• 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: (1S,3Z)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oct-3-en-7-yne-1,6-diol
• 英文别名: (Z,1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oct-3-en-7-yne-1,6-diol
• CAS: 444885-26-1
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: NSSSOVKHENYHQK-GTLALWSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3Z)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oct-3-en-7-yne-1,6-diol 在 dicobalt octacarbonyl 、 三氟化硼乙醚 、 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.41h， 以68%的产率得到(2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-ethynyl-2,3,6,7-tetrahydrooxepine
  参考文献：
  名称：

  Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes

  摘要：

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00046-7
• 作为产物：
  描述：

  (S)-7-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-yne-1,2-diol 在 Lindlar's catalyst 喹啉 、 sodium periodate 、 正丁基锂 、 四丁基氟化铵 、 氢气 、 四丁基高碘酸铵 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 (1S,3Z)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]oct-3-en-7-yne-1,6-diol
  参考文献：
  名称：

  Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes

  摘要：

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00046-7

文献信息

• Stereoselective synthesis of syn-2,7-disubstituted-4,5-oxepenes
  作者：David D Dı́az、Juan M Betancort、Fernando R.P Crisóstomo、Tomás Martı́n、Vı́ctor S Martı́n

  DOI：10.1016/s0040-4020(02)00046-7

  日期：2002.3

  An efficient synthesis of the title compounds as pure enantiomers is reported. The method is based on the intramolecular trapping group of a carbocation generated by acid treatment of exo-Co-2(CO)(6)-propargyl alcohols by a stereochemically controlled secondary hydroxy a up located in a suitable chain. (C) 2002 Elsevier Science Ltd. All rights reserved.