(S)-2-cycloocten-1-yl benzoate

• 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: (S)-2-cycloocten-1-yl benzoate
• 英文别名: (S)-2-cyclooctenyl-1-benzoate；(S)-2-cyclooctenyl benzoate；[(1S,2Z)-cyclooct-2-en-1-yl] benzoate
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: LYTXONHVZRXCLG-SMJHDNPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  顺-环辛烯 、 过氧化苯甲酸叔丁酯 在 copper(II) bis(trifluoromethanesulfonate) 、 苯肼 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (R)-2-cycloocten-1-yl benzoate 、 (S)-2-cycloocten-1-yl benzoate
  参考文献：
  名称：

  使用手性pybox配体的Cu（I）络合物催化的过酸酯催化烯烃的对映选择性烯丙基氧化。

  摘要：

  通过在室温下选择配体和perester的独特组合，可以调节催化量的Cu（I）-pybox配合物与各种过酸酯的烯烃的对映选择性烯丙基氧化，以实现高不对称诱导（最高98％ee）。温度。反应中的不对称诱导在很大程度上取决于与过酸酯的芳环相连的取代基的性质。对于高对映选择性而言，在C-5处存在宝石二苯基和在恶唑啉环的手性中心（C-4）处存在仲或叔烷基取代基是至关重要的。已提出并讨论了pi-pi堆积模型以解释反应的立体化学结果。

  DOI：

  10.1039/b612423b

文献信息

• Enantioselective oxidation of olefins catalyzed by chiral copper bis(oxazolinyl)pyridine complexes: a reassessment
  作者：Sandeep K. Ginotra、Vinod K. Singh

  DOI：10.1016/j.tet.2006.01.093

  日期：2006.4

  Copper complexes of chiral tridentate pybox ligands synthesized using a modified procedure have been studied as catalysts for the enantioselective allylic oxidation of olefins. A variety of olefins have been used in this reaction. Using 5 mol% of a Cu(II) complex of the tridentate pybox ligand, phenylhydrazine, and tert-butyl perbenzoate as oxidant in acetone, optically active allylic benzoates were

  已经研究了使用改良方法合成的手性三齿pybox配体的铜配合物，作为烯烃的对映选择性烯丙基氧化的催化剂。在该反应中已经使用了多种烯烃。用5％（摩尔）的Cu（II）的复合物中的三齿配位体pybox，苯肼，和叔用过苯甲酸丁酯作为丙酮中的氧化剂，在数小时内获得了高达94％ee的旋光烯丙基苯甲酸酯。还观察到在反应中使用分子筛不会改变对映选择性。发现温度对于烯烃的对映选择性烯丙基氧化的速率非常关键。使用EPR光谱已显示，苯肼和苯hydr将Cu（II）物种还原为Cu（I），但与后者相比，前者的还原速度更快。结论是速率的提高不是苯肼或苯hydr的存在所特有的，但是如果使用丙酮作为溶剂，两者的作用是相同的。
• Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst
  作者：Ken-ichi Kawasaki、Tsutomu Katsuki

  DOI：10.1016/s0040-4020(97)00322-0

  日期：1997.5

  Optically active copper(II)-tris(oxazoline) complex that was synthesized as a model compound of the active site of non-heme oxygenase, was found to catalyze allylic oxidation of cycloalkenes to give the corresponding 2-cycloalkenyl benzoates with moderate to excellent enantioselectivity (up to 93% ee) under the Kharash-Sosnovsky reaction conditions. (C) 1997 Elsevier Science Ltd.
• Asymmetric allylic oxidation of cycloalkenes using a tridentate tris(oxazoline) ligand as a chiral auxiliary
  作者：Yoshinori Kohmura、Tsutomu Katsuki

  DOI：10.1016/s0040-4039(00)00522-0

  日期：2000.5

  A tridentate tris(oxazoline) ligand (4b) was found to be an efficient chiral auxiliary for copper-mediated asymmetric allylic oxidation (Kharash-Sosnovsky reaction) of cycloalkenes. Regardless of the ring size of the substrate, the reaction examined showed good enantioselectivity higher than 81% ee. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Asymmetric Kharasch Reaction:  Catalytic Enantioselective Allylic Oxidation of Olefins Using Chiral Pyridine Bis(diphenyloxazoline)−Copper Complexes and <i>tert</i>-Butyl Perbenzoate^,
  作者：Govindasamy Sekar、Arpita DattaGupta、Vinod K. Singh

  DOI：10.1021/jo972132p

  日期：1998.5.1

  Copper complexes of chiral pyridine bis(diphenyloxazoline)-type ligands have been studied as catalysts for the enantioselective allylic oxidation of olefins. Using 2.5-5 mol % of these chiral catalysts and tert-butyl perbenzoate as oxidant, optically active allylic benzoates were obtained in up to 86% ee. A variety of copper salts was studied under different conditions and in different solvents. Acetone was found to be a superior solvent for the reaction. Use of phenylhydrazine in conjunction with the chiral copper complex played a crucial role in increasing the rate of the reaction. Use of 4 Angstrom molecular sieves increased the optical yield of product in almost every case.
• Chiral bipyridine–copper(I) complex-catalyzed enantioselective allylic oxidation of cyclic alkenes
  作者：Wing-Sze Lee、Hoi-Lun Kwong、Hoi-Ling Chan、Wing-Wai Choi、Lai-Yuen Ng

  DOI：10.1016/s0957-4166(01)00160-4

  日期：2001.5

  Chiral copper(I) bipyridine complexes were prepared and used as catalysts in the enantioselective allylic oxidation of cyclic alkenes with tert-butyl perbenzoate. The yields ranged From moderate to good and enantioselectivities up to 70% were observed. (C) 2001 Elsevier Science Ltd. All rights reserved.