(1S,3Z)-9-benzyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-3-en-7-yne-1,6-diol | 444885-17-0

• 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)-9-benzyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-3-en-7-yne-1,6-diol
• 英文别名: (Z,1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-9-phenylmethoxynon-3-en-7-yne-1,6-diol
• CAS: 444885-17-0
• 化学式: C₂₁H₂₈O₅
• 分子量: 360.45
• InChiKey: VSSUWYJAEJNMKN-XTNJDRRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3Z)-9-benzyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-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79%的产率得到(7S)-2-[3-(benzyloxy)prop-1-ynyl]-7-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-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：

  苄基丙炔基醚 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 (1S,3Z)-9-benzyloxy-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-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.