1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(6-methoxynaphthalen-2-yl)prop-2-yn-1-ol | 1239477-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(6-methoxynaphthalen-2-yl)prop-2-yn-1-ol
• CAS: 1239477-48-5
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: GVNZUSOTPVARCB-QRWMCTBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(6-methoxynaphthalen-2-yl)prop-2-yn-1-ol 在 dicobalt octacarbonyl 、 二乙胺基三氟化硫 、 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 12.25h， 生成 (R)-4-((S)-1-fluoro-3-(6-methoxynaphthalen-2-yl)prop-2-ynyl)-2,2-dimethyl-1,3-dioxolane 、 (R)-4-((R)-1-fluoro-3-(6-methoxynaphthalen-2-yl)prop-2-ynyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Diastereoselective synthesis of propargylic fluorides and its application in preparation of monofluorinated sugar

  摘要：

  An effective method to diastereoselectively synthesize enantioenriched propargylic fluorides was developed via S(N)1 type reaction of DAST participated dehydroxy-fluorination of diastereomeric propargylic alcohol cobalt carbonyl complexes. A serious of propargylic fluorides can be prepared by this approach in good yields with moderate to high diastereoselectivities. To demonstrate the application of this approach in synthesis, monofluorinated sugar 12, an important and versatile building block, was prepared in an efficient manner. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.078
• 作为产物：
  描述：

  2-乙炔基-6-甲氧基萘 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(6-methoxynaphthalen-2-yl)prop-2-yn-1-ol
  参考文献：
  名称：

  Diastereoselective synthesis of propargylic fluorides and its application in preparation of monofluorinated sugar

  摘要：

  An effective method to diastereoselectively synthesize enantioenriched propargylic fluorides was developed via S(N)1 type reaction of DAST participated dehydroxy-fluorination of diastereomeric propargylic alcohol cobalt carbonyl complexes. A serious of propargylic fluorides can be prepared by this approach in good yields with moderate to high diastereoselectivities. To demonstrate the application of this approach in synthesis, monofluorinated sugar 12, an important and versatile building block, was prepared in an efficient manner. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.078