R-(+)-2,2-diphenylmethyloxirane | 86433-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: R-(+)-2,2-diphenylmethyloxirane
• 英文别名: 1,1-diphenyl-1,2-epoxypropane；Oxirane, 3-methyl-2,2-diphenyl-, (3R)-；(3R)-3-methyl-2,2-diphenyloxirane
• CAS: 86433-03-6
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: ZYFFGPUROADGLV-GFCCVEGCSA-N

物化性质

• 沸点：
  312.4±11.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙醇 、 R-(+)-2,2-diphenylmethyloxirane 、 三苯基氧化膦 在 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 1-ethoxy-1,1-diphenyl-2-propanol
  参考文献：
  名称：

  Lewis acid promoted decomposition of substituted 1,3,2.lambda.5-dioxaphospholanes. Kinetic and thermodynamic studies

  摘要：

  DOI：

  10.1021/jo00271a039
• 作为产物：
  描述：

  (S)-(-)-1,1-二苯基-1,2-丙二醇 在 lithium bromide 作用下， 以 甲苯 为溶剂， 反应 27.0h， 生成 R-(+)-2,2-diphenylmethyloxirane
  参考文献：
  名称：

  Lewis acid promoted decomposition of substituted 1,3,2.lambda.5-dioxaphospholanes. Kinetic and thermodynamic studies

  摘要：

  DOI：

  10.1021/jo00271a039

文献信息

• Convenient asymmetric (salen)Mn(III)-catalyzed epoxidation of unfunctionalized alkenes with hydrogen peroxide using carboxylate salt cocatalysts
  作者：Pekka Pietikäinen

  DOI：10.1016/s0040-4020(98)00145-8

  日期：1998.4

  Asymmetric epoxidation of unfunctionalized alkenes is reported using chiral (salen)Mn(III) complexes 1–5 together with a carboxylate salt cocatalyst in the presence of either aqueous H2O2 or anhydrous urea-H2O2 adduct as oxidant. Several simple soluble salts (acetates, formates, benzoates) were studied all giving good yields of epoxides with moderate to excellent enantioselectivity. For example, 1

  据报道，在含水H 2 O 2或无水脲-H 2 O 2加合物存在下，使用手性（salen）Mn（III）配合物1-5和羧酸盐助催化剂，未官能化烯烃的不对称环氧化反应。研究了几种简单的可溶性盐（乙酸盐，甲酸盐，苯甲酸盐），它们均具有良好的环氧化物收率，且具有中等至出色的对映选择性。例如，以84％的产率将1，1-二苯-1-丙烯转化为96％ee的相应环氧化物。通常，该环氧化方法比使用氮杂环作为助催化剂的前述系统产生更好的结果。
• Highly Enantioselective, Catalytic Epoxidation of Trisubstituted Olefins
  作者：Bridget D. Brandes、Eric N. Jacobsen

  DOI：10.1021/jo00095a009

  日期：1994.8

  Chiral (salen)Mn(III) complexes have been found to be highly selective catalysts for the asymmetric epoxidation of several cyclic and acyclic trisubstituted olefins. These results are interpreted with a transition-state model for epoxidation involving a skewed, side-on approach of olefin to a (salen)Mn(oxo) intermediate.
• Asymmetric Epoxidation of Unfunctionalized Alkenes with Ammonium and Phosphonium Monopersulfates Catalyzed by Chiral Mn(III)–Salen Complexes
  作者：Pekka Pietikäinen

  DOI：10.1016/s0040-4020(99)01008-x

  日期：2000.1

  Simple cis-disubstituted and trisubstituted alkenes were enantioselectively epoxidized in mild conditions using various Mn(III)-salen complexes as catalysts and quaternary ammonium and phosphonium monopersulfates (Bu4NHSO5, Ph4PHSO5) as oxidants together with amine N-oxides as additives. The effect of the catalyst structure on the stereochemical outcome of the epoxidation reactions was studied. Generally, the 1,2-diphenylethylenediamine-derived complexes were found to give higher asymmetric induction compared to their 1,2-diaminocyclohexane-derived counterparts. Particularly high yields of epoxides (up to 98%) and good enantiomeric excesses (ee up to 93%) were obtained in the epoxidation of 2,2-dialkylchromenes and trisubstituted alkenes. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Vasi, I. G.; Acharya, R. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 1, p. 67 - 68
  作者：Vasi, I. G.、Acharya, R. H.

  DOI：——

  日期：——
• VASI, I. G.;ACHARYA, R. H., INDIAN J. CHEM., 1983, 22, N 1, 67-68
  作者：VASI, I. G.、ACHARYA, R. H.

  DOI：——

  日期：——