ethyl 2-(8-oxo-1,4-dioxaspiro[4.5]decan-7-yl)acetate | 1027377-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(8-oxo-1,4-dioxaspiro[4.5]decan-7-yl)acetate
• CAS: 1027377-64-5
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: AKJLEAPKZCPUGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(8-oxo-1,4-dioxaspiro[4.5]decan-7-yl)acetate 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 1,10-菲罗啉 、 三氟化硼乙醚 、 双氧水 、 potassium tri-sec-butyl-borohydride 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.75h， 生成 (3R,3aR,7aR)-3-Methyl-tetrahydro-benzofuran-2,5-dione
  参考文献：
  名称：

  Unusual Facial Selectivity in the Cycloaddition of Singlet Oxygen to a Simple Cyclic Diene¹

  摘要：

  Syntheses of 5-isopropyl-1,3-cyclohexadiene and syn-5-isopropyl-2,3-dioxabicyclo[2.2.2]octane, by routes that would allow completely diastereoselective introduction of deuterium labels, are described. The reaction of the isopropyl cyclohexadiene with singlet oxygen is shown to give an endoperoxide that is derived by preferential attack on the more sterically hindered face of the diene, A possible mechanistic explanation of this result is that the attack from the less hindered face leads to ''ene'' reaction rather than endoperoxide formation, However, this mechanism would require that the ''ene'' reaction and cycloaddition proceed via a common intermediate-presumably a perepoxide.

  DOI：

  10.1021/jo9604292
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 、 溴乙酸乙酯 在 lithium diisopropyl amide 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以80%的产率得到ethyl 2-(8-oxo-1,4-dioxaspiro[4.5]decan-7-yl)acetate
  参考文献：
  名称：

  agastaquinone 的全合成，一种从 Agastache rugosa 中分离的二萜醌

  摘要：

  Agastaquinone 是一种从 Agastache rugose 中分离出来的三环二萜类化合物。基于芳基内酯的分子内Friedel-Crafts酰化完成了阿司他醌的首次全合成...

  DOI：

  10.1080/00397911.2020.1825742

文献信息

• Synthetic Study of Carbocyclic Core of Cortistatin A, an Anti-Angiogenic Steroidal Alkaloid from Marine Sponge
  作者：Naoyuki Kotoku、Motomasa Kobayashi、Yuji Sumii、Takeshi Hayashi

  DOI：10.3987/com-11-12195

  日期：——

  Synthesis of carbocyclic core of cortistatin A (1), a novel anti-angiogenic steroidal alkaloid from Indonesian marine sponge, was investigated. Intramolecular Heck cyclization using substrate 18 achieved construction of 7-membered B-ring structure. The presence of steric hindrance around the reaction center was found to favor endo cyclization pathway in this substrate.
• A Short Path to Erythrina Alkaloid Derivatives
  作者：Le Anh Tuan、Gun-Cheol Kim

  DOI：10.5012/bkcs.2010.31.6.1800

  日期：2010.6.20
• Total synthesis of agastaquinone, a diterpenoid quinone isolated from <i>Agastache rugosa</i>
  作者：Sangku Lee、Jisu Yoo、Jae-Kyung Jung、Jae Nyoung Kim、Myeong Sik Yoon

  DOI：10.1080/00397911.2020.1825742

  日期：2021.1.2

  Agastaquinone is a tricyclic diterpenoid isolated from Agastache rugose. The first total synthesis of agastaquinone was accomplished based on intramolecular Friedel-Crafts acylation of aryl lactone...

  Agastaquinone 是一种从 Agastache rugose 中分离出来的三环二萜类化合物。基于芳基内酯的分子内Friedel-Crafts酰化完成了阿司他醌的首次全合成...
• Unusual Facial Selectivity in the Cycloaddition of Singlet Oxygen to a Simple Cyclic Diene¹
  作者：Kelly M. Davis、Barry K. Carpenter

  DOI：10.1021/jo9604292

  日期：1996.1.1

  Syntheses of 5-isopropyl-1,3-cyclohexadiene and syn-5-isopropyl-2,3-dioxabicyclo[2.2.2]octane, by routes that would allow completely diastereoselective introduction of deuterium labels, are described. The reaction of the isopropyl cyclohexadiene with singlet oxygen is shown to give an endoperoxide that is derived by preferential attack on the more sterically hindered face of the diene, A possible mechanistic explanation of this result is that the attack from the less hindered face leads to ''ene'' reaction rather than endoperoxide formation, However, this mechanism would require that the ''ene'' reaction and cycloaddition proceed via a common intermediate-presumably a perepoxide.