(1SR,2RS)-2-hydroxy-2-phenylcyclohexyl acetate | 23313-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1SR,2RS)-2-hydroxy-2-phenylcyclohexyl acetate
• 英文别名: 2-hydroxy-2-phenylcyclohexyl acetate
• CAS: 23313-43-1；23313-44-2；99942-90-2；134750-71-3；134750-72-4；134780-69-1；134780-70-4；134780-71-5
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: LHIJTJFFVNLKEW-KGLIPLIRSA-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)：
  2.38
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1SR,2RS)-2-hydroxy-2-phenylcyclohexyl acetate 在 pig liver esterase sodium hydride 、 氟硼酸钾 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,18R)-1-phenyl-2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosane
  参考文献：
  名称：

  Naemura, Koichiro; Miyabe, Hajime; Shingai, Yasuhiro, Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 957 - 959

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯基-1-环已烯 、 溶剂黄146 在 sodium periodate 、 copper(l) iodide 、 L-脯氨酸 作用下， 以62%的产率得到(1SR,2RS)-2-hydroxy-2-phenylcyclohexyl acetate
  参考文献：
  名称：

  CuI/l-proline-catalyzed selective one-step mono-acylation of styrenes and stilbenes

  摘要：

  Vicinal di-oxygenation of styrene-type olefins was achieved with cheaper, less toxic Cul in the presence of L-proline as ligand and NalO(4) as the oxidant. This approach provides a straightforward and efficient access to mono-acylated diols from both styrene and stilbene derivatives with good to excellent yields and diastereoselectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.084

文献信息

• Vicinal Difunctionalization of Alkenes under Iodine(III) Catalysis involving Lewis Base Adducts
  作者：Kristina Aertker、Raquel J. Rama、Julita Opalach、Kilian Muñiz

  DOI：10.1002/adsc.201601178

  日期：2017.4.17

  by X‐ray analysis. This arrangement was shown to generate a kinetically competent superior catalyst structure for the catalytic dioxygenation of alkenes. It introduces the concept of Lewis base adduct formation as a kinetic factor in iodine(I/III) catalysis.

  探索了2-吡啶基取代基对芳基碘化物在碘（III）化学中作为催化剂的催化性能的影响。通过X射线分析鉴定并确认了吡啶氮与亲电子碘（III）中心之间的有效Lewis碱加合物。已显示该布置产生了用于烯烃的催化双加氧的动力学上称能的优异催化剂结构。它介绍了路易斯碱加合物形成的概念，它是碘（I / III）催化中的动力学因子。
• A rapid 1,2-dihydroxylation of alkenes using a lipase and hydrogen peroxide under microwave conditions
  作者：Kuladip Sarma、Naleen Borthakur、Amrit Goswami

  DOI：10.1016/j.tetlet.2007.07.087

  日期：2007.9

  The combined advantages of using an enzyme immobilized lipase from Pseudomonas sp [PSLG6], hydrogen peroxide, ethyl acetate and microwave irradiation for the dihydroxylation of olefins are reported. (c) 2007 Elsevier Ltd. All rights reserved.
• Enantioselective acylation of alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify the faster reacting enantiomer of an alcohol in this acylation
  作者：Koichiro Naemura、Masaki Murata、Rie Tanaka、Masashi Yano、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(96)00186-3

  日期：1996.6

  Lipase QL-catalyzed acylation of secondary alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether gave preferentially the corresponding acetate with an R configuration. On the basis of the results, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a secondary alcohol reacts faster in this reaction. (C) 1996 Elsevier Science Ltd
• Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation
  作者：Koichiro Naemura、Masaki Murata、Rie Tanaka、Masashi Yano、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(96)00429-6

  日期：1996.11

  Lipase QL (from Alcaligenes sp.)-catalyzed acylation of alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether converted preferentially primary alcohols with an S configuration and secondary alcohols with an R configuration into the corresponding homochiral acetates. On the basis of observed enantiomer selectivities, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation. Copyright (C) 1996 Published by Elsevier Science Ltd