(E)-methyl 6-oxo-6-phenylhex-4-enoate | 690660-80-1

• 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: (E)-methyl 6-oxo-6-phenylhex-4-enoate
• 英文别名: methyl (E)-6-oxo-6-phenylhex-4-enoate
• CAS: 690660-80-1
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: ZXTODIWSDYLZCE-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Dimethylzinc 、 (E)-methyl 6-oxo-6-phenylhex-4-enoate 在 copper(II) bis(trifluoromethanesulfonate) 、 亚磷酸三乙酯 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到
  参考文献：
  名称：

  Copper-Catalyzed Tandem Conjugate Addition−Electrophilic Trapping:  Ketones, Esters, and Nitriles as Terminal Electrophiles

  摘要：

  Exposure of enone substrates 1a-18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones, esters, and nitriles as terminal electrophiles in Cu-catalyzed conjugate addition-electrophilic trapping.

  DOI：

  10.1021/ja030603l
• 作为产物：
  描述：

  N-甲基-N-甲基苯甲酰胺 在 Grubbs Catalyst C₈₂₇ 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-methyl 6-oxo-6-phenylhex-4-enoate
  参考文献：
  名称：

  Preparation and evaluation of deconstruction analogues of 7-deoxykalafungin as AKT kinase inhibitors

  摘要：

  The pyranonaphthoquinone (PNQ) lactone natural products, including 7-deoxykalafungin, have been reported to be potent and selective covalent inhibitors of AKT kinase. In this work we seek to identify structural features of the natural product scaffold that are essential for potency and selectivity. Using a deconstruction approach, we designed and prepared simplified analogues of 7-deoxykalafungin. Testing of the compounds for their ability to inhibit AKT and the closely related kinase PKA revealed that the 3,6-dihydro-2H-pyran ring of the PNQ lactones is required for potent and selective inhibition of AKT. We have also unexpectedly identified a new submicromolar inhibitor of PKA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.020

文献信息

• Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition
  作者：Luoqiang Zhang、Mengxin Zhao、Maoping Pu、Zhaoming Ma、Jingsong Zhou、Caiyou Chen、Yun-Dong Wu、Yonggui Robin Chi、Jianrong Steve Zhou

  DOI：10.1021/jacs.2c05678

  日期：2022.11.9

  A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary

  异喹诺酮的镍络合物直接使用芳基和杂芳基卤化物促进烯酮的对映选择性共轭芳基化和杂芳基化。该反应成功应用于ar -turmerone、(+)-tolterodine和AZD5672手性片段的立体选择性合成。从机理上讲，实验和计算支持芳基镍 (I) 络合物通过基本 1,4-加成插入到烯酮中。
• Copper-Catalyzed Tandem Conjugate Addition−Electrophilic Trapping:  Ketones, Esters, and Nitriles as Terminal Electrophiles
  作者：Kyriacos Agapiou、David F. Cauble、Michael J. Krische

  DOI：10.1021/ja030603l

  日期：2004.4.1

  Exposure of enone substrates 1a-18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones, esters, and nitriles as terminal electrophiles in Cu-catalyzed conjugate addition-electrophilic trapping.
• Preparation and evaluation of deconstruction analogues of 7-deoxykalafungin as AKT kinase inhibitors
  作者：Sudha Korwar、Thuy Nguyen、Keith C. Ellis

  DOI：10.1016/j.bmcl.2013.11.020

  日期：2014.1

  The pyranonaphthoquinone (PNQ) lactone natural products, including 7-deoxykalafungin, have been reported to be potent and selective covalent inhibitors of AKT kinase. In this work we seek to identify structural features of the natural product scaffold that are essential for potency and selectivity. Using a deconstruction approach, we designed and prepared simplified analogues of 7-deoxykalafungin. Testing of the compounds for their ability to inhibit AKT and the closely related kinase PKA revealed that the 3,6-dihydro-2H-pyran ring of the PNQ lactones is required for potent and selective inhibition of AKT. We have also unexpectedly identified a new submicromolar inhibitor of PKA. (C) 2013 Elsevier Ltd. All rights reserved.