2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl pivalate | 1314806-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl pivalate
• 英文别名: [2-(1,3-Benzodioxol-5-yl)-2-oxoethyl] 2,2-dimethylpropanoate
• CAS: 1314806-35-3
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: XSTGAWDREIWIQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl pivalate 在 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 、 palladium(II) trifluoroacetate 、 氢气 作用下， 以 乙醇 、 2,2,2-三氟乙醇 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 反应 24.0h， 以95%的产率得到
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Hydrogenation of α-Acyloxy-1-arylethanones

  摘要：

  First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol.

  DOI：

  10.1002/anie.201306231
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 溴 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl pivalate
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Hydrogenation of α-Acyloxy-1-arylethanones

  摘要：

  First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol.

  DOI：

  10.1002/anie.201306231

文献信息

• Palladium-Catalyzed Chemo- and Enantioselective C−O Bond Cleavage of α-Acyloxy Ketones by Hydrogenolysis
  作者：Jianzhong Chen、Zhenfeng Zhang、Delong Liu、Wanbin Zhang

  DOI：10.1002/anie.201603590

  日期：2016.7.11

  A chemoselective C−O bond cleavage of the ester alkyl side‐chain of α‐acyloxy ketones was realized for the first time by a highly efficient palladium‐catalyzed hydrogenolysis (S/C=6000, the highest catalytic efficiency by far). Furthermore, a kinetic resolution of α‐acyloxy ketones was first developed by enantioselective hydrogenolysis with good yields and up to 99 % ee.

  通过高效钯催化的氢解反应（S / C = 6000，迄今为止最高的催化效率），首次实现了α-酰氧基酮的酯烷基侧链的化学选择性C-O键断裂。此外，首先通过对映选择性氢解反应开发了α-酰氧基酮的动力学拆分方法，该方法具有良好的收率和高达99％ee的收率。
• Arylation of α-pivaloxyl ketones with arylboronic reagents via Ni-catalyzed sp3 C–O activation
  作者：Kun Huang、Gang Li、Wei-Ping Huang、Da-Gang Yu、Zhang-Jie Shi

  DOI：10.1039/c1cc11193k

  日期：——

  A Suzuki–Miyaura coupling of α-pivaloxyl ketonesviaNi-catalyzed sp3 C–O activation to produce α-aryl ketones is developed. This study offers a convenient method to construct α-arylation products from readily available α-hydroxyl carbonyl compounds.

  开发了一种通过镍催化的sp3 C–O活化将α-皮伐氧基酮与α-芳基酮进行Suzuki–Miyaura耦合的方法。本研究提供了一种便利的方法，以便从易得的α-羟基羰基化合物构建α-芳基化产物。