(-)-(S)-1,1-diphenylpropene oxide | 33739-88-7

• 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: (-)-(S)-1,1-diphenylpropene oxide
• 英文别名: (3S)-2,2-diphenyl-3-methyloxirane；(-)-(S)-1,1-diphenylprop-1-ene oxide；(3S)-3-methyl-2,2-diphenyloxirane
• CAS: 33739-88-7
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: ZYFFGPUROADGLV-LBPRGKRZSA-N

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：

  哌啶 、 (-)-(S)-1,1-diphenylpropene oxide 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以97%的产率得到(R)-2-(piperidin-1-yl)-1,1-diphenyl-propan-1-ol
  参考文献：
  名称：

  Structural Optimization of Enantiopure 2-Cyclialkylamino-2-aryl-1,1-diphenylethanols as Catalytic Ligands for Enantioselective Additions to Aldehydes

  摘要：

  The structural optimization of a family of modular, enantiopure beta-amino alcohol ligands with a common 2-amino-2-aryl-1,1-diphenylethanol skeleton, whose stereogenicity was introduced through the Jacobsen epoxidation of 1,1-diphenyl-2-arylethylenes, has led to the identification of a small set of optimal catalysts with enhanced activity and enantioselectivity in the addition of alkylzinc and arylzinc reagents to aldehydes. Criteria for the discrimination between apparently analogous, highly enantioselective ligands are proposed.

  DOI：

  10.1021/jo800615d
• 作为产物：
  描述：

  1-甲基-2,2-二苯基乙烯 在 Jacobsen's catalyst 4-苯基吡啶-N-氧化物 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-(S)-1,1-diphenylpropene oxide
  参考文献：
  名称：

  Structural Optimization of Enantiopure 2-Cyclialkylamino-2-aryl-1,1-diphenylethanols as Catalytic Ligands for Enantioselective Additions to Aldehydes

  摘要：

  The structural optimization of a family of modular, enantiopure beta-amino alcohol ligands with a common 2-amino-2-aryl-1,1-diphenylethanol skeleton, whose stereogenicity was introduced through the Jacobsen epoxidation of 1,1-diphenyl-2-arylethylenes, has led to the identification of a small set of optimal catalysts with enhanced activity and enantioselectivity in the addition of alkylzinc and arylzinc reagents to aldehydes. Criteria for the discrimination between apparently analogous, highly enantioselective ligands are proposed.

  DOI：

  10.1021/jo800615d

文献信息

• Highly Enantioselective Biphasic Iminium-Catalyzed Epoxidation of Alkenes. On the Importance of the Counterion and of N(<i>sp</i>²)C(<i>sp</i>³) Rotamers
  作者：Roman Novikov、Gérald Bernardinelli、Jérôme Lacour

  DOI：10.1002/adsc.200800778

  日期：2009.3

  Abstractmagnified imageDiastereomeric biaryliminium cations made of an (Ra)‐5,5′,6,6′,7,7′,8,8′‐octahydrobinaphthyl core and exocyclic appendages derived from (S)‐ or (R)‐3,3‐dimethylbutan‐2‐amine are effective asymmetric epoxidation catalysts for unfunctionalized alkenes. Herein, we report that the negative counterion of the iminium salts has to be chosen wisely. While the hexafluoroantimonate anion [SbF6−] is optimal for reliable results, one has to be careful about other anions and tetraphenylborate [BPh4−] in particular. We also detail that the so far unexplained “lack” of stereochemical control from the chiral exocyclic appendage in this type of catalysts is due to the existence of atropisomers around the N(sp2)C(sp3) bond that links the azepinium core to the exocyclic stereocenter. Finally, we develop a general model to predict with certainty the high selectivity in the formation of non‐racemic epoxides of defined absolute configuration.
• 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.
• Asymmetric Mn(III)-salen catalyzed epoxidation of unfunctionalized alkenes with tetrabutylammonium monopersulfate
  作者：Pekka Pietikäinen

  DOI：10.1016/s0040-4039(98)02468-x

  日期：1999.1

  Asymmetric Mn(III)-salen catalyzed epoxidation of simple cis-disubstituted and trisubstituted alkenes in mild conditions was performed using tetrabutylammonium monopersulfate (Bu4NHSO5) as the oxidant together with N-methylmorpholine N-oxide as an additive. Particularly high yields of epoxides (up to 97 %) and good enantiomeric excesses (ee up to 93 %) were obtained in the epoxidation of 2,2-dialkylchromenes and trisubstituted alkenes. (C) 1999 Elsevier Science Ltd. All rights reserved.
• EPOXIDE HYDROLASE COMPLEXES AND METHODS THEREWITH
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP1154764A1

  公开（公告）日：2001-11-21