benzyl 2-(benzo[d][1,3]dioxol-5-yl)-2-oxoacetate | 1449336-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-(benzo[d][1,3]dioxol-5-yl)-2-oxoacetate
• CAS: 1449336-19-9
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: BRRIDRSLULAEAA-UHFFFAOYSA-N

物化性质

• 沸点：
  452.4±44.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-(benzo[d][1,3]dioxol-5-yl)-2-oxoacetate 在 (R,R)-QuinoxP 、 氢气 、 palladium diacetate 、 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 24.0h， 生成 (S)-benzyl 2-(benzo[d][1,3]dioxol-5-yl)-2-((4-methylphenyl)sulfonamido)acetate
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

  摘要：

  An efficient Pd(OAc)(2)-catalyzed asymmetric hydrogenation of alpha-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)(2), a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)(2) which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral alpha-arylglycine fragments are widely found in many chiral products and bioactive molecules.

  DOI：

  10.1021/acs.orglett.9b03452
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 吡啶 、 selenium(IV) oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲基叔丁基醚 为溶剂， 反应 6.0h， 生成 benzyl 2-(benzo[d][1,3]dioxol-5-yl)-2-oxoacetate
  参考文献：
  名称：

  Pd(OAc)₂-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

  摘要：

  An efficient Pd(OAc)(2)-catalyzed asymmetric hydrogenation of alpha-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)(2), a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)(2) which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral alpha-arylglycine fragments are widely found in many chiral products and bioactive molecules.

  DOI：

  10.1021/acs.orglett.9b03452

文献信息

• 2-Oxo promoted hydrophosphonylation & aerobic intramolecular nucleophilic displacement reaction
  作者：Satyanarayana Battula、Narsaiah Battini、Deepika Singh、Qazi Naveed Ahmed

  DOI：10.1039/c5ob01310k

  日期：——

  the tervalent phosphite form towards 2-oxoaldehydes in the synthesis of α-hydroxy-β-oxophosphonates. The in situ activated α-C–H atom of α-hydroxy-β-oxophosphonates sustains aerobic intramolecular nucleophilic displacement in a curious way to produce α-oxoester.

  已经描述了用于合成α-羟基-β-氧代膦酸酯和α-氧代酯的高效无催化剂方法。α-氧代醛中存在2-氧代基团是促进α-羟基-β-氧代膦酸酯合成中三价亚磷酸酯形式向2-氧代醛类反应的关键因素。在原位以奇特的方式，以产生α氧代酯α羟基-β-oxophosphonates维持有氧分子内亲核置换的活化α-C-H原子。
• Organocatalyzed Formal [2 + 2] Cycloaddition of Ketimines with Allenoates: Facile Access to Azetidines with a Chiral Tetrasubstituted Carbon Stereogenic Center
  作者：Shinobu Takizawa、Fernando Arteaga Arteaga、Yasushi Yoshida、Michitaka Suzuki、Hiroaki Sasai

  DOI：10.1021/ol401817q

  日期：2013.8.16

  An enantioselective organocatalyzed aza-MBH-type reaction of ketimines and allenoates has been developed. The present formal [2 + 2] cycloaddition produces highly functionalized azetidines with a chiral tetrasubstituted carbon stereogenic center in good to excellent yields and high enantioselectivities.