(2S,3R)-2-cyclohexyl-2,3-epoxy-1,4-naphthoquinone | 105016-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,3R)-2-cyclohexyl-2,3-epoxy-1,4-naphthoquinone
• 英文别名: (2S,3R)-2-cyclohexyl-2,3-epoxynaphthoquinone；(1aS,7aR)-1a-cyclohexyl-7aH-naphtho[2,3-b]oxirene-2,7-dione
• CAS: 105016-64-6
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: QCRPCWBQVBABJO-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-环己基-1,4-萘醌 在 双氧水 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 (2S,3R)-2-cyclohexyl-2,3-epoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Enantioselective epoxidation of 2-substituted 1,4-naphthoquinones using gem-dihydroperoxides

  摘要：

  New gem-dihydroperoxides were successfully used for DBU-promoted enantioselective epoxidation of 2-substituted 1,4-naphtlloquinones. The corresponding 1,4-naphthoquinone epoxides were obtained in yields up to 97% and ee's up to 82%. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.096

文献信息

• Asymmetric weitz - scheffer epoxidation promoted by bovine serum albumin
  作者：Stefano Colona、Nicoletta Gaggero、Amedea Manfredil、Massimo Spadoni、Luigi Casella、Giacomo Carrea、Piero Pasta

  DOI：10.1016/s0040-4020(01)86023-3

  日期：1988.1

  The epoxidation of 2-substituted naphthoquinones with t-BuOOH in an aqueous buffer solution containing a small amount (up to 5 % molar equiv) of bovine serum albumin (BSA) gives the corresponding epoxides with enantiomeric excess (e.e.) up to 100 %. The enantioselectivity is very sensitive to the addition of water miscible or immiscible cosolvents and to the length of the alkyl chain in position 2

  2-叔萘醌在含有少量（最高5％摩尔当量）牛血清白蛋白（BSA）的缓冲水溶液中用t-BuOOH环氧化，得到相应的环氧化物，其对映体过量（ee）最高为100％。对映选择性对与水混溶或不混溶的助溶剂的添加以及位置2上烷基链的长度非常敏感。研究了助溶剂影响ee的机理。发现了BSA-醌配合物的圆二色性光谱与环氧化产物的立体化学之间的相关性。
• Catalytic asymmetric epoxidation of enones under phase-transfer catalyzed conditions
  作者：Shigeru Arai、Hiroki Tsuge、Makoto Oku、Motoko Miura、Takayuki Shioiri

  DOI：10.1016/s0040-4020(02)00028-5

  日期：2002.2

  The development of the catalytic asymmetric epoxidation of enones promoted by aqueous H2O2 with chiral quaternary ammonium salts is described. The reaction smoothly proceeded to give alpha,beta-epoxyketones with satisfactory enantioselectivities in both the trans and cis enone systems (up to 92% ee) by use of cinchonine or quinidine derivatives (5 mol%) as phase transfer catalysts. (C) 2002 Elsevier Science Ltd. All tights reserved.
• Catalytic asymmetric weitz-scheffer epoxidation promoted by bovine serum albumin. Part II
  作者：Stefano Colonna、Amedea Manfredi、Rita Annunziata、Massimo Spadoni

  DOI：10.1016/s0040-4020(01)86797-1

  日期：1987.1
• The effect of organic cosolvents on the enantioselectivity in the bovine serum albumin catalyzed Weitz-Scheffer condensation.
  作者：Stefano Colonna、Amedea Manfredi、Massimo Spadoni

  DOI：10.1016/s0040-4039(01)81046-7

  日期：1987.1
• Catalytic asymmetric weitz-scheffer reaction in the presence of bovine serum albumin
  作者：Stefano Colonna、Amedea Manfredi

  DOI：10.1016/s0040-4039(00)84026-5

  日期：1986.1