tert-butyl 2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 923569-24-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: tert-butyl 2-hydroxy-1-tetralone-2-carboxylate；tert-butyl (S)-2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate；tert-butyl (2S)-2-hydroxy-1-oxo-3,4-dihydronaphthalene-2-carboxylate
• CAS: 923569-24-8
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: YOVWPLLYBJFCRO-HNNXBMFYSA-N

物化性质

• 沸点：
  375.9±42.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 过氧化氢异丙苯 、 C₅₅H₆₉F₁₂N₇O₂*ClH 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以60%的产率得到tert-butyl 2-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  在过氧化异丙苯存在下，使用胍-尿素双功能有机催化剂对四氢酮衍生的β-酮酸酯的不对称α-羟基氧化反应

  摘要：

  通过使用胍-脲双功能有机催化剂在安全，可商购获得的氢过氧化枯烯（CHP）的存在下，实现了对1-四氢萘酮衍生的β-酮酸酯的高度对映选择性催化氧化。以99％的产率获得了α-羟基化产物，对映体过量（ee）高达95％。目前的氧化方法已成功地用于合成抗癌药柔红霉素的关键中间体（2）。

  DOI：

  10.1002/chem.201303006

文献信息

• Organocatalytic Oxyamination of Azlactones: Kinetic Resolution of Oxaziridines and Asymmetric Synthesis of Oxazolin-4-ones
  作者：Shunxi Dong、Xiaohua Liu、Yin Zhu、Peng He、Lili Lin、Xiaoming Feng

  DOI：10.1021/ja404379n

  日期：2013.7.10

  example of oxyamination of azlactones with oxaziridines was realized using a chiral bisguanidinium salt. Efficient catalytic asymmetric oxyamination and kinetic resolution of oxaziridines occurred simultaneously. Various chiral oxazolin-4-one derivatives with potential biological activity were obtained (up to 92% ee). Meanwhile, a series of optically pure oxaziridines were recovered with up to 99% ee and

  使用手性双胍盐实现吖内酯与恶氮丙啶氧胺化的第一个实例。氧氮丙啶的高效催化不对称氧化胺化和动力学拆分同时发生。获得了具有潜在生物活性的各种手性 oxazolin-4-one 衍生物（高达 92% ee）。同时，回收了一系列光学纯氧氮杂环丙烷，ee 高达 99%，并成功用于 3-甲基-1H-吲哚和苯乙烯的不对称氧化胺化。还通过对照实验研究了三重立体分化过程。
• Iron(iii)–salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles
  作者：Xin Gu、Yan Zhang、Zhen-Jiang Xu、Chi-Ming Che

  DOI：10.1039/c4cc01631a

  日期：——

  Chiral iron(III)–salan complexes catalysed highly enantioselective α-fluorination and α-hydroxylation of β-keto esters and N-Boc oxindoles to give the corresponding products in high yields and good-to-excellent ee values under mild reaction conditions.

  手性铁(III)–salan复合物催化了β-酮酯和N-Boc氧杂环戊烯的高度对映选择性α-氟化和α-羟基化反应，在温和的反应条件下获得相应产物，产率高，对映体过量值良好至优异。
• Bifunctional Ammonium Salt Catalyzed Asymmetric α-Hydroxylation of β-Ketoesters by Simultaneous Resolution of Oxaziridines
  作者：Johanna Novacek、Joseph A. Izzo、Mathew J. Vetticatt、Mario Waser

  DOI：10.1002/chem.201604153

  日期：2016.11.21

  Chiral bifunctional urea‐containing ammonium salts were found to be very efficient catalysts for asymmetric α‐hydroxylation reactions of β‐ketoesters with oxaziridines under base‐free conditions. The reaction is accompanied by a simultaneous kinetic resolution of the oxaziridine and a plausible and so far unprecedented bifunctional transition‐state model has been obtained by means of DFT calculations

  发现在无碱条件下，手性双官能含脲铵盐是β-酮酯与恶唑烷的不对称α-羟基化反应的非常有效的催化剂。该反应伴随有恶唑烷的同时动力学拆分，并且已经通过DFT计算获得了似乎可行的，迄今为止前所未有的双功能过渡态模型。
• Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
  作者：Minami Odagi、Kan Takayama、Makoto Sato、Masahiro Yamanaka、Kazuo Nagasawa

  DOI：10.3390/molecules200712590

  日期：——

  guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety.

  在DFT计算的指导下，设计了在胍上带有手性吡咯烷部分的新型胍-双脲双功能有机催化剂5。检查得到的有机催化剂5的四氢萘酮衍生的β-酮酯的α-羟基化，并且用带有含甲氧基甲基醚的手性吡咯烷部分的5j获得了良好的选择性。
• Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters
  作者：Christopher Mairhofer、Johanna Novacek、Mario Waser

  DOI：10.1021/acs.orglett.0c02198

  日期：2020.8.7

  synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H2O2. The reaction proceeds via in situ formation of a hypervalent iodine species, which then reacts with the used aldimine to generate an activated electrophilic oxygen transfer reagent.

  手性双官能碘化铵催化剂与简单的催化相关的醛亚胺的协同使用可实现前所未有的使用H 2 O 2的β-酮酸酯的不对称α-羟基化反应。该反应通过原位形成高价碘物质进行，然后与用过的醛亚胺反应生成活化的亲电子氧转移试剂。