(S)-4-(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-ol | 1187768-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-ol
• 英文别名: (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-phenylmethoxybut-2-yn-1-ol
• CAS: 1187768-79-1
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: CNCQMXWRZZLROT-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-ol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-4-((R)-4-(benzyloxy)-1-fluorobut-2-ynyl)-2,2-dimethyl-1,3-dioxolane 、 (R)-4-((S)-4-(benzyloxy)-1-fluorobut-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：

  (S)-4-(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ynyl acetate 在 potassium carbonate 、 水 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以93%的产率得到(S)-4-(benzyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-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

文献信息

• A regio- and stereoisomeric study of allylic alcohol fluorination with a range of reagents
  作者：Stefano Bresciani、Alexandra M.Z. Slawin、David O’Hagan

  DOI：10.1016/j.jfluchem.2009.03.003

  日期：2009.6

  A range of dehydroxyfluorination reagents was reacted with separate diastereoisomers of a chiral allylic alcohol to explore both the regio- and stereoselectivity ratios of direct versus allylic fluorination. The allylic alcohol stereoisomers gave the same predominant fluorinated diastereoisomer indicating that the reaction proceeds with a significant S(N)1 component via an allylic carbocation intermediate, which is quenched by fluoride ion, predominantly from the least hindered face. None of the reagents displayed very high regio- or stereoselectivity, although in all cases the allylic fluorination products predominated. (c) 2009 Elsevier B.V. All rights reserved.
• Diastereoselective synthesis of propargylic fluorides and its application in preparation of monofluorinated sugar
  作者：Shilu Fan、Chun-Yang He、Xingang Zhang

  DOI：10.1016/j.tet.2010.04.078

  日期：2010.7

  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.