(2R,3R,4S,5S,6S)­‐3,5­‐dimethyl-­2,6­‐diphenyltetrahydro-­2H­‐pyran-­4­‐ol | 69291-50-5

• 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: (2R,3R,4S,5S,6S)­‐3,5­‐dimethyl-­2,6­‐diphenyltetrahydro-­2H­‐pyran-­4­‐ol
• 英文别名: c-2,c-6-diphenyl-t-3,t-5-dimethyloxan-r-4-ol；cis-2,6-Diphenyl-trans-3,5-dimethyloxan-r-4-ol；c-2,c-6-diphenyl-t-3,t-5-dimethyloxolan-r-4-ol；(2R,3R,4S,5S,6S)­-3,5­-dimethyl-­2,6­-diphenyltetrahydro-­2H­-pyran-­4­-ol
• CAS: 69291-50-5
• 化学式: C₁₉H₂₂O₂
• 分子量: 282.382
• InChiKey: VXPIFLGYTUZDRP-DGMGRSIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6S)­‐3,5­‐dimethyl-­2,6­‐diphenyltetrahydro-­2H­‐pyran-­4­‐ol 在 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 吡啶 为溶剂， 反应 20.0h， 生成 trans-2,6-diphenyl-cis-3,5-dimethyl-4-acetylamino-oxane
  参考文献：
  名称：

  Preparation and stereochemistry of some substituted 2,6-diphenyl-4-aminotetrahydropyrans

  摘要：

  DOI：

  10.1021/jo01310a018
• 作为产物：
  描述：

  、 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54%的产率得到(2R,3R,4S,5S,6S)­‐3,5­‐dimethyl-­2,6­‐diphenyltetrahydro-­2H­‐pyran-­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：——
• 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
  作者：Kuppusamy Selvaraj、Vinayagam Venkateswaran、Krishnasamy Ramarajan

  DOI：10.1002/kin.550260806

  日期：1994.8

  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.
• 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：——