cis-2,6-Diphenyl-trans-3-methyloxan-r-4-ol | 69291-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: cis-2,6-Diphenyl-trans-3-methyloxan-r-4-ol
• 英文别名: c-2,c-6-diphenyl-t-3-methyloxan-r-4-ol；(2S,3S,4R,6R)-3-methyl-2,6-diphenyloxan-4-ol
• CAS: 69291-48-1
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: NRQSCUZQQVBWIF-LIRZEXBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-2,6-Diphenyl-trans-3-methyloxan-r-4-ol 在 高氯酸 、 N-chloro-r-2,c-6-diphenyl-t-3-methylpiperidin-4-one 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 3-methyl-2,6-diphenyl-tetrahydropyran-4-one
  参考文献：
  名称：

  Kinetics of oxidation of heterocyclic secondary alcohols byN-chloro-r-2,c-6-diphenyl-t-3 methyl piperidin-4-one (NCP) in perchloric acid medium

  摘要：

  AbstractAn investigation of the kinetics of oxidation of epimeric piperidin‐4‐ols, oxan‐4‐ols, and cyclohexanol by N‐chloro‐r‐2, c‐6‐diphenyl‐t‐3‐methylpiperidin‐4‐one (NCP) in aqueous acetic acid in the presence of perchloric acid shows that the reaction is first‐order each in substrate and oxidant. Both H3O+ and Cl− which catalyze the reaction, exhibit a fractional order kinetics. While increase in ionic strength increases the rate slightly, an inverse dependence is observed between rate and solvent polarity. Addition of r‐2‐c‐6‐diphenyl‐t‐3‐methylpiperidin‐4‐one, one of the reaction products, did not influence the rate. Also, no kinetic isotope effect has been observed. A plausible mechanism consistent with these observations is proposed and the relative reactivities of the substrates are explained on conformational grounds. © 1994 John Wiley & Sons, Inc.

  DOI：

  10.1002/kin.550260806
• 作为产物：
  描述：

  2-[(2R)-but-3-en-2-yl]-5,5-dimethyl-1,3,2-dioxaborinane 、 苯甲醛 在 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 10.75h， 以45%的产率得到cis-2,6-Diphenyl-trans-3-methyloxan-r-4-ol
  参考文献：
  名称：

  One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation–borylation, allylation and Prins cyclisation reactions

  摘要：

  2,3,4,5,6-Pentasubstituted tetrahydropyrans have been prepared in good yield (42-57%) with excellent dr (>95:5) and er (>95:5) using a one-pot lithiation-borylation, allylation and Prins cyclisation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.091

文献信息

• Jambulingam, M.; Nanjappan, P.; Natarajan, K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 390 - 394
  作者：Jambulingam, M.、Nanjappan, P.、Natarajan, K.、Ramalingam, K.

  DOI：——

  日期：——
• Natarajan, K.; Jambulingam, M.; Selvaraj, K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 9, p. 901 - 903
  作者：Natarajan, K.、Jambulingam, M.、Selvaraj, K.、Nanjappan, P.、Ramalingam, K.

  DOI：——

  日期：——
• Jambulingam, Marimuthu; Napjappan, Palaniappan; Natarajan, Kumarasamy, Journal of the Chemical Society. Perkin transactions II, 1985, p. 1699 - 1702
  作者：Jambulingam, Marimuthu、Napjappan, Palaniappan、Natarajan, Kumarasamy、Nagalingam, Jpgiah、Palaniswamy, Maran、et al.

  DOI：——

  日期：——
• Arjunan, Periaswamy Gounder; Lakshmanan, Joghee Gowder; Chandrasekara, Nallappan, Journal of the Chemical Society. Perkin transactions II, 1985, p. 1183 - 1186
  作者：Arjunan, Periaswamy Gounder、Lakshmanan, Joghee Gowder、Chandrasekara, Nallappan、Ramalingam, Kondareddiar、Selvaraj, Kuppusamy

  DOI：——

  日期：——
• Sureshkumar, Shanmugham; Chandrasekara, Nallappan; Ramalingam, Kondareddiar, Journal of the Chemical Society. Perkin transactions II, 1985, p. 311 - 314
  作者：Sureshkumar, Shanmugham、Chandrasekara, Nallappan、Ramalingam, Kondareddiar、Selvaraj, Kuppusamy

  DOI：——

  日期：——