4,4-Dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one | 1262324-62-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 4,4-Dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one
• CAS: 1262324-62-8
• 化学式: C₁₅H₂₇BO₃
• 分子量: 266.189
• InChiKey: DKNACOLCQDEPOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-Dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one 在 potassium hydrogen bifluoride 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到
  参考文献：
  名称：

  Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

  摘要：

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

  DOI：

  10.1021/jo1019738
• 作为产物：
  描述：

  2,2-二甲基-4-戊烯酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.0h， 生成 4,4-Dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hept-6-en-3-one
  参考文献：
  名称：

  Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

  摘要：

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

  DOI：

  10.1021/jo1019738

文献信息

• Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators
  作者：Christoph Schnabel、Katja Sterz、Henrik Müller、Julia Rehbein、Michael Wiese、Martin Hiersemann

  DOI：10.1021/jo1019738

  日期：2011.1.21

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.