cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester | 23313-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester
• 英文别名: cis-acetic acid 2-hydroxy-2-phenylcyclohexyl ester；acetic acid 2-hydroxy-2-phenylcyclohexyl ester；(+/-)-cis-2-Acetoxy-1-phenylcyclohexanol；syn-2-hydroxy-2-phenylcyclohexyl acetate；2-hydroxy-2-phenylcyclohexyl acetate；cis-2-acetoxy-1-phenylcyclohexanol；[(1S,2S)-2-hydroxy-2-phenylcyclohexyl] acetate
• CAS: 23313-43-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: LHIJTJFFVNLKEW-KBPBESRZSA-N

物化性质

• 沸点：
  345.5±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester 在 diethylaluminum benzenethiolate 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 以68%的产率得到2-苯基环己酮
  参考文献：
  名称：

  有机铝化合物促进vic-二醇单乙酸酯的重排

  摘要：

  用有机铝试剂 R3Al 处理频哪醇单乙酸酯导致在 R 作为亲核试剂在所得羰基碳上吸收时发生重排，而 R2AlSPh 在处理后产生频哪醇本身。

  DOI：

  10.1246/bcsj.55.3941
• 作为产物：
  描述：

  1-苯基-1-环已烯 在 吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 生成 cis-acetic acid 2-hydroxy-2-phenyl-cyclohexyl ester
  参考文献：
  名称：

  有机铝化合物促进vic-二醇单乙酸酯的重排

  摘要：

  用有机铝试剂 R3Al 处理频哪醇单乙酸酯导致在 R 作为亲核试剂在所得羰基碳上吸收时发生重排，而 R2AlSPh 在处理后产生频哪醇本身。

  DOI：

  10.1246/bcsj.55.3941

文献信息

• Synthesis of β-acetoxy alcohols by PhI(OAc)₂-mediated metal-free diastereoselective β-acetoxylation of alcohols
  作者：Chun-Yang Zhao、Liang-Gui Li、Qing-Rong Liu、Cheng-Xue Pan、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1039/c6ob01203e

  日期：——

  β-Acetoxy alcohols can be synthesized in good yields with excellent diastereoselectivity from tertiary alcohols through PhI(OAc)2-mediated metal-free β-acetoxylation. Mechanistic studies showed that the β-acetoxylation process might undergo dehydration and sequential highly regioselective and diastereoseletive dioxygenation. Gram scale and diverse useful scaffolds could be prepared via this β-acetoxylation

  β-乙酰氧基醇可以通过PhI（OAc）2介导的无金属β-乙酰氧基化反应从叔醇中以良好的非对映选择性高收率合成。机理研究表明，β-乙酰氧基化过程可能会发生脱水，继而发生高度区域选择性和非对映异构的双加氧反应。可以通过该β-乙酰氧基化方法制备革兰氏规模和各种有用的支架。
• Preparation and enantiomer recognition behaviour of azophenolic crown ethers containing cis-1-phenylcyclohexane-l,2-diol as the chiral subunit and 2,4-dinitrophenylazophenol as the chromophore
  作者：Koichiro Naemura、Koji Ueno、Sachiko Takeuchi、Keiji Hirose、Yoshito Tobe、Takahiro Kaneda、Yoshiteru Sakata

  DOI：10.1039/p19960000383

  日期：——

  Optically active azophenolic crown ethers 1 and 2 incorporating two cis-1-phenylcyclohexane-1,2-diol chiral subunits and a p-(2,4-dinitrophenylazo)phenol moiety as a chromophore have been prepared and the enantiomer recognitive coloration in complexation with chiral ethylamine and 2-aminoethanol derivatives has been examined. The observed enantiomer selectivities of crown ethers 1 and 2 have been interpreted

  制备了具有两个顺式-1-苯基环己烷-1,2-二醇手性亚基和对-（2,4-二硝基苯基偶氮）苯酚部分作为生色团的旋光偶氮酚冠醚1和2 ，该对映体可识别成色，与已经研究了手性乙胺和2-氨基乙醇衍生物。基于对映异构体配合物的CPK分子模型检查，可以解释冠醚1和2所观察到的对映异构体选择性。
• Chemo-, Regio-, and Stereoselective Synthesis of syn-Aryl Glycol Monoesters from Aryl Olefins with Hydrogen Peroxide Catalyzed by RuCl3
  作者：Chunbao Li、Yanqiao Zhang、Guobiao Chu、Xiaoxue Cui、Zhijie Han、Daoke Dou、Yuanli Chen、Xiaosong Yu

  DOI：10.1055/s-0029-1219553

  日期：2010.4

  Chemo-, regio-, and stereoselectivity have been achieved in the oxidations of aryl olefins. The aryl olefins were oxidized by 2 equivalents of H2O2 in acetic acid, catalyzed by 0.02 equivalent of RuCl3, leading to the formations of syn-aryl glycol monoesters. As the reaction is concerted, both the regio- and stereo­selectivity are excellent. In the presence of aliphatic C=C bonds, the aryl C=C bonds were selectively dioxygenated. This represents the first example of chemoselective dioxygenation of aryl C=C bonds.

  在芳基烯烃的氧化反应中实现了化学选择性、区域选择性和立体选择性。芳基烯烃在醋酸中由2当量的H2O2氧化，催化剂为0.02当量的RuCl3，生成了syn-芳基甘油单酯。由于反应是协同进行的，因此区域选择性和立体选择性均表现优异。在脂肪烃C=C键的存在下，芳基C=C键被选择性二氧化。 这是芳基C=C键化学选择性二氧化的第一个例子。
• The Nature of the Catalytically Active Species in Olefin Dioxygenation with PhI(OAc)₂: Metal or Proton?
  作者：Yan-Biao Kang、Lutz H. Gade

  DOI：10.1021/ja110805b

  日期：2011.3.16

  Evidence for the protiocatalytic nature of the diacetoxylation of alkenes using PhI(OAc)(2) as oxidant is presented. Systematic studies into the catalytic activity in the presence of proton-trapping and metal-complexing agents indicate that protons act as catalysts in the reaction. Using triflic acid as catalyst, the selectivity and reaction rate of the conversion is similar or superior to most efficient metal-based catalysts. Metal cations, such as Pd(II) and Cu(II), may interact with the oxidant in the initiation phase of the catalytic transformation; however, 1 equiv of strong acid is produced in the first cycle which then functions as the active catalyst. Based on a kinetic study as well as in situ mass spectrometry, a mechanistic cycle for the proton-catalyzed reaction, which is consistent with all experimental data presented in this work, is proposed.
• Palladium-Catalyzed Olefin Dioxygenation
  作者：Yang Li、Datong Song、Vy M. Dong

  DOI：10.1021/ja711029u

  日期：2008.3.1

  A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and Phl(OAC)(2) as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An (18)O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.