(3R,4R)-3-methyl-4-(2-phenylethyl)oxetan-2-one | 1057557-51-3

• 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: (3R,4R)-3-methyl-4-(2-phenylethyl)oxetan-2-one
• 英文别名: (3R,4R)-trans-3-methyl-4-(2-phenylethyl)-oxetan-2-one
• CAS: 1057557-51-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: OAOSLDXADFZCIG-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯丙醛 、 丙酰溴 在 2Br^(1-)*C₄₁H₅₁AlN₄O₂⁽²⁺⁾ 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 trans-(+/-)-3-methyl-4-(2-phenylethyl)oxetan-2-one 、 (3R,4R)-3-methyl-4-(2-phenylethyl)oxetan-2-one
  参考文献：
  名称：

  反式β-内酯的催化不对称合成：路易斯酸和离子对催化的协同作用

  摘要：

  描述了酰基卤与脂肪族醛（提供3,4-二取代的β-内酯）的首次反式选择性催化不对称[2 + 2]环缩合反应的发展。这项工作在不对称双活化催化的背景下利用了一种新的策略：它将路易斯酸和有机质子惰性离子对催化的概念结合在一个单一的催化剂体系中。该方法还可以应用于芳族醛，并具有广泛的适用性（29个示例）。亲核开环反应进一步证明了其实用性，该反应提供了高度对映体富集的抗醛醇缩合产物。

  DOI：

  10.1002/chem.201000840

文献信息

• Catalytic Asymmetric Synthesis of trans-Configured β-Lactones: Cooperation of Lewis Acid and Ion Pair Catalysis
  作者：Thomas Kull、José Cabrera、René Peters

  DOI：10.1002/chem.201000840

  日期：——

  development of the first trans‐selective catalytic asymmetric [2+2] cyclocondensation of acyl halides with aliphatic aldehydes furnishing 3,4‐disubstituted β‐lactones is described. This work made use of a new strategy within the context of asymmetric dual activation catalysis: it combines the concepts of Lewis acid and organic aprotic ion pair catalysis in a single catalyst system. The methodology could

  描述了酰基卤与脂肪族醛（提供3,4-二取代的β-内酯）的首次反式选择性催化不对称[2 + 2]环缩合反应的发展。这项工作在不对称双活化催化的背景下利用了一种新的策略：它将路易斯酸和有机质子惰性离子对催化的概念结合在一个单一的催化剂体系中。该方法还可以应用于芳族醛，并具有广泛的适用性（29个示例）。亲核开环反应进一步证明了其实用性，该反应提供了高度对映体富集的抗醛醇缩合产物。
• Contact Ion Pair Directed Lewis Acid Catalysis: Asymmetric Synthesis of<i>trans</i>‐Configured β‐Lactones
  作者：Thomas Kull、René Peters

  DOI：10.1002/anie.200801143

  日期：2008.7.7
• Inhibition of fatty acid synthase by beta-lactones and other compounds for inhibition of cellular proliferation
  申请人：——

  公开号：US20040024050A1

  公开（公告）日：2004-02-05

  The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis.
• [EN] INHIBITION OF FATTY ACID SYNTHASE BY BETA-LACTONES AND OTHER COMPOUNDS FOR INHIBITION OF CELLULAR PROLIFERATION<br/>[FR] INHIBITION DE SYNTHASE D'ACIDE GRAS PAR BETA-LACTONES ET PAR D'AUTRES COMPOSES DESTINES A INHIBER LA PROLIFERATION CELLULAIRE
  申请人：BURNHAM INST

  公开号：WO2003088975A1

  公开（公告）日：2003-10-30

  The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis.
• Cooperative Al(Salen)-Pyridinium Catalysts for the Asymmetric Synthesis of trans-Configured β-Lactones by [2+2]-Cyclocondensation of Acylbromides and Aldehydes: Investigation of Pyridinium Substituent Effects
  作者：Patrick Meier、Florian Broghammer、Katja Latendorf、Guntram Rauhut、René Peters

  DOI：10.3390/molecules17067121

  日期：——

  Recently, we have reported the first catalyst which is capable of forming trans-β-lactones with high enantioselectivity from aliphatic (and aromatic) aldehyde substrates by cyclocondensation with acyl bromides. In that previous study the concepts of Lewis acid and organic aprotic ion pair catalysis were combined in a salen-type catalyst molecule. Since a pyridinium residue on the salen periphery is essential

  β-内酯的反式选择性催化不对称形成构成了抗醛醇添加物的有吸引力的替代物。最近，我们报道了第一种能够通过与酰基溴环缩合从脂肪族（和芳香族）醛底物形成具有高对映选择性的反式-β-内酯的催化剂。在之前的研究中，路易斯酸和有机非质子离子对催化的概念被结合在一个萨伦型催化剂分子中。由于salen外围的吡啶鎓残基对于高反式和对映选择性至关重要，我们感兴趣的是吡啶鎓环上的取代基是否可用于进一步提高催化剂效率的问题，因为它们可能对有效杂环内的电荷。因此，在本研究中，我们比较了一个小型的铝盐/双吡啶鎓催化剂库，主要区别在于吡啶鎓残基上的取代基。作为这些研究的一个结果，确定了一种新催化剂，与之前报道的最佳催化剂相比，该催化剂具有略微优越的立体选择性。NBO 计算表明，较高的立体选择性不能用有效电荷的变化来解释。