5-[(2-Methyl-1,3-dioxolan-2-yl)methyl]-4-(2-oxoethyl)furan-3-carbaldehyde | 1351488-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(2-Methyl-1,3-dioxolan-2-yl)methyl]-4-(2-oxoethyl)furan-3-carbaldehyde
• 英文别名: 5-[(2-methyl-1,3-dioxolan-2-yl)methyl]-4-(2-oxoethyl)furan-3-carbaldehyde
• CAS: 1351488-27-1
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: YNJSUBQOJOFCDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2'-(prop-1-ene-1,3-diyl)bis(1,3,2-dioxaborolane) 、 5-[(2-Methyl-1,3-dioxolan-2-yl)methyl]-4-(2-oxoethyl)furan-3-carbaldehyde 以 乙醚 为溶剂， 反应 28.0h， 以10.1 mg的产率得到1-((2-methyl-1,3-dioxolan-2-yl)methyl)-4,5,8,9-tetrahydrocycloocta[c]furan-4,8-diol
  参考文献：
  名称：

  Efficient and straightforward preparation of a building block for (−)-teubrevin G synthesis via chemically diversed oriented synthesis

  摘要：

  A rapid and efficient methodology to highly functionalised molecular units well suited as scaffolds for diversity-oriented molecular construction in the synthesis of natural products is reported herein. A key macrocyclic intermediate in the synthesis of the neo-clerodane diterpene (-)-teubrevin G was successfully synthesized in a 5-step sequence in a 70% overall yield using a novel intramolecular coupling between an allylborating agent and a 1,5-dialdehyde moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.112
• 作为产物：
  描述：

  2-甲基-1,3-二氧戊环-2-乙醛 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 三丁基膦 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 53.0h， 生成 5-[(2-Methyl-1,3-dioxolan-2-yl)methyl]-4-(2-oxoethyl)furan-3-carbaldehyde
  参考文献：
  名称：

  Efficient and straightforward preparation of a building block for (−)-teubrevin G synthesis via chemically diversed oriented synthesis

  摘要：

  A rapid and efficient methodology to highly functionalised molecular units well suited as scaffolds for diversity-oriented molecular construction in the synthesis of natural products is reported herein. A key macrocyclic intermediate in the synthesis of the neo-clerodane diterpene (-)-teubrevin G was successfully synthesized in a 5-step sequence in a 70% overall yield using a novel intramolecular coupling between an allylborating agent and a 1,5-dialdehyde moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.112

文献信息

• Efficient and straightforward preparation of a building block for (−)-teubrevin G synthesis via chemically diversed oriented synthesis
  作者：Daniel Garcia Velazquez、Rafael Luque

  DOI：10.1016/j.tetlet.2011.10.112

  日期：2011.12

  A rapid and efficient methodology to highly functionalised molecular units well suited as scaffolds for diversity-oriented molecular construction in the synthesis of natural products is reported herein. A key macrocyclic intermediate in the synthesis of the neo-clerodane diterpene (-)-teubrevin G was successfully synthesized in a 5-step sequence in a 70% overall yield using a novel intramolecular coupling between an allylborating agent and a 1,5-dialdehyde moiety. (C) 2011 Elsevier Ltd. All rights reserved.