(4R)-4-[(1S)-2,2-dimethyl-1-prop-2-ynoxybut-3-enyl]-2,2-dimethyl-1,3-dioxolane | 1235548-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-4-[(1S)-2,2-dimethyl-1-prop-2-ynoxybut-3-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 1235548-20-5
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: QLGIYMYPNZBWLK-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(1S)-2,2-dimethyl-1-prop-2-ynoxybut-3-enyl]-2,2-dimethyl-1,3-dioxolane 在 正丁基锂 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以61%的产率得到C₁₄H₂₁⁽²⁾HO₃
  参考文献：
  名称：

  Gold-catalyzed direct cycloketalization of acetonide-tethered alkynes in the presence of water

  摘要：

  A methodology for the direct preparation of bridged acetals from acetonide-tethered alkynes under gold catalysis in the presence of water has been developed. The bicyclic ring structures bearing a bridged five-membered ring arise from the regioselective bis-oxycyclization by initial attack of the oxygen atom to the internal alkyne carbon. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.030
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 在 indium 、 四丁基碘化铵 、 氯化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (4R)-4-[(1S)-2,2-dimethyl-1-prop-2-ynoxybut-3-enyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Gold-catalyzed direct cycloketalization of acetonide-tethered alkynes in the presence of water

  摘要：

  A methodology for the direct preparation of bridged acetals from acetonide-tethered alkynes under gold catalysis in the presence of water has been developed. The bicyclic ring structures bearing a bridged five-membered ring arise from the regioselective bis-oxycyclization by initial attack of the oxygen atom to the internal alkyne carbon. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.030

文献信息

• Gold/Acid-Cocatalyzed Regiodivergent Preparation of Bridged Ketals via Direct Bis-Oxycyclization of Alkynic Acetonides
  作者：Benito Alcaide、Pedro Almendros、Rocío Carrascosa、M. Rosario Torres

  DOI：10.1002/adsc.201000124

  日期：——

  The regioselective metal/acid co‐catalyzed direct bis‐oxycyclization of alkynyldioxolanes allows the efficient synthesis of optically pure bi‐ and tricyclic bridged acetal systems.

  炔基二氧戊环的区域选择性金属/酸共催化直接双氧环化反应可有效合成光学纯的双环和三环桥缩醛体系。
• Gold-catalyzed direct cycloketalization of acetonide-tethered alkynes in the presence of water
  作者：Benito Alcaide、Pedro Almendros、Rocío Carrascosa

  DOI：10.1016/j.tet.2012.09.030

  日期：2012.11

  A methodology for the direct preparation of bridged acetals from acetonide-tethered alkynes under gold catalysis in the presence of water has been developed. The bicyclic ring structures bearing a bridged five-membered ring arise from the regioselective bis-oxycyclization by initial attack of the oxygen atom to the internal alkyne carbon. (C) 2012 Elsevier Ltd. All rights reserved.