(1R,2S,4R,5S)-methyl 2-hydroxy-9-oxo-4-phenylbicyclo[3.3.1]nonane-2-carboxylate | 956584-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,4R,5S)-methyl 2-hydroxy-9-oxo-4-phenylbicyclo[3.3.1]nonane-2-carboxylate
• 英文别名: methyl (1R,2S,4R,5S)-2-hydroxy-9-oxo-4-phenylbicyclo[3.3.1]nonane-2-carboxylate
• CAS: 956584-44-4
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: PWOYBGBEHMUWFK-WSMBLCCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,5S)-methyl 2-hydroxy-9-oxo-4-phenylbicyclo[3.3.1]nonane-2-carboxylate 在 lithium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到methyl (1S,2S,4S,5R)-4-hydroxy-10-oxo-2-phenyl-9-oxabicyclo[3.3.2]decane-4-carboxylate
  参考文献：
  名称：

  Enantioselective Formal [3+3] Annulation for the Direct Construction of Bicyclic Skeletons with Four Stereogenic Centers

  摘要：

  An enantioselective formal [3+3] annulation reaction of cyclic ketones with enones has been developed. In the presence of 20 mol % of pyrrolidine-thiourea la or N-(pyrrolidin-2-ylmethyl)trifluoromethanesulfonamide 1i, the reactions afford bicyclo [3.3.1] adducts in moderate to good yields with good to high enantioselectivities under mild conditions.

  DOI：

  10.1021/ol701669b
• 作为产物：
  描述：

  potassium (E)-2-oxo-4-phenylbut-3-enoate 在 氢氧化钾 作用下， 生成 (1R,2S,4R,5S)-methyl 2-hydroxy-9-oxo-4-phenylbicyclo[3.3.1]nonane-2-carboxylate
  参考文献：
  名称：

  Jung,L., Bulletin de la Societe Chimique de France, 1967, p. 4696 - 4701

  摘要：

  DOI：

文献信息

• Synthesis of a New N-Diaminophosphoryl-N′-[(2S)-2-pyrrolidinylmethyl]thiourea as a Chiral Organocatalyst for the Stereoselective Michael Addition of Cyclohexanone to Nitrostyrenes and Chalcones - Application in Cascade Processes for the Synthesis of Polyc
  作者：Carlos Cruz-Hernández、Eduardo Martínez-Martínez、Perla E. Hernández-González、Eusebio Juaristi

  DOI：10.1002/ejoc.201801339

  日期：2018.12.31

  novel chiral thiourea containing a segment of privileged (2S)‐2‐pyrrolidinylmetan‐amine as well as a hydrophobic phosphoramide framework is described. The new organocatalyst exhibited good performance in asymmetric Michael additions, in a variety of systems including the formal [3+3] cyclization of cyclohexanone with arylidenepyruvates through a cascade process, which involves the asymmetric Michael

  描述了一种新颖的手性硫脲的合成，该硫脲含有一个特权级的（2 S）-2-吡咯烷基二甲胺和疏水性磷酰胺骨架。新型有机催化剂在不对称迈克尔加成反应中表现出良好的性能，在多种系统中，包括通过级联过程与芳基丙酮酸戊酯对环己酮进行正式的[3 + 3]环化反应，该过程涉及不对称迈克尔加成反应/质子转移/非对映选择性醛醇缩合反应。
• Highly Enantioselective Reactions of Cyclohexanone and<i>β</i>,<i>γ</i>-Unsaturated<i>α</i>-Keto Ester: The Tuning of Chemo-selectivities by Secondary and Primary Amine Catalysts
  作者：Jianwei Wei、Wengang Guo、Xin Zhou、Xin Du、Yan Liu、Can Li

  DOI：10.1002/cjoc.201400431

  日期：2014.10

  amphiphilic imidazole based secondary and primary amine catalysts were synthesized and shown to be very effective with an acid cocatalyst for the asymmetric reaction of cyclohexanone to β,γ‐unsaturated α‐keto ester. Interestingly, primary and secondary amine catalysts show different regio‐selectivities in this reaction. Under the catalysis of secondary amine 1, excellent enantioselectivities were observed for

  合成了一系列基于两亲咪唑的仲胺和伯胺催化剂，它们显示出与酸助催化剂非常有效地使环己酮不对称反应成β，γ-不饱和α-酮酯。有趣的是，伯胺和仲胺催化剂在该反应中显示出不同的区域选择性。在仲胺1的催化下，以水为溶剂，环己酮与β，γ-不饱和α-酮酯直接3 + 3反应生成的产物具有极好的对映选择性。而且，相同的反应物被伯胺2催化导致醛醇缩合反应，从而提供具有高非对映选择性和高达97％ee的相应产物。使用气相模型对过渡态进行的理论研究表明，空间效应对仲胺1和伯胺2的不同化学选择性诱导起着重要作用。
• Multifunctional phosphoramide-(<i>S</i>)-prolinamide derivatives as efficient organocatalysts in asymmetric aldol and Michael reactions
  作者：Carlos Cruz-Hernández、José M. Landeros、Eusebio Juaristi

  DOI：10.1039/c9nj00300b

  日期：——

  The synthesis and evaluation of three novel chiral organocatalysts derived from (S)-proline and containing a bis-amidophosphoryl amine fragment are reported. The structure and conformation of the new compounds were determined by NMR spectroscopy and X-ray crystallographic analysis. The present study represents an effort directed to enhance the performance of (S)-proline-derived organocatalysts in asymmetric

  报道了三种衍生自（S）-脯氨酸并含有双-氨基磷酰基胺片段的新型手性有机催化剂的合成和评价。通过NMR光谱和X射线晶体学分析确定了新化合物的结构和构象。本研究代表了旨在提高（S）性能的努力。脯氨酸衍生的有机催化剂在不对称的醇醛和迈克尔反应中，是由于在催化剂中掺入萘基部分而引起的空间相互作用增加。结果，用萘基取代基实现的立体选择性与用苯基类似物获得的立体选择性相当。尽管如此，新的有机催化剂在与各种靛红和芳基甲醛的醛醇缩合反应中仍表现出相当好的对映体和非对映体选择性，提供的产品具有高达94：6的非对映体比例和高达95：5的对映体比例。表现出高达96：4的非对映体比例和高达98：2的对映体比例。