2-[(S)-4-((S)-sec-butyl)-4,5-dihydrooxazol-2-yl]phenol | 500129-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(S)-4-((S)-sec-butyl)-4,5-dihydrooxazol-2-yl]phenol
• 英文别名: 2-[(S)-4-sec-butyl-4,5-dihydrooxazol-2-yl]phenol；6-[(4S)-4-[(2S)-butan-2-yl]-1,3-oxazolidin-2-ylidene]cyclohexa-2,4-dien-1-one；2-[(4S)-4-[(2S)-butan-2-yl]-4,5-dihydro-1,3-oxazol-2-yl]phenol
• CAS: 500129-82-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: XVERADVZARCDSV-GXSJLCMTSA-N

物化性质

• 沸点：
  342.0±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(1,1′-联萘-2,2′-二氧)氯膦 、 2-[(S)-4-((S)-sec-butyl)-4,5-dihydrooxazol-2-yl]phenol 在 三乙胺 作用下， 以 甲苯 为溶剂， 以74%的产率得到(S)-2-[2''-((4'''S)-4'''-sec-butyl-2'''-oxazolin-2'''-yl)phenoxy]dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin
  参考文献：
  名称：

  烯丙基底物与手性亚磷酸酯配体在 Pd、Ir 和 Rh 配合物上的区域特异性和立体选择性烷基化

  摘要：

  DOI：

  10.1134/s0012500807070026

文献信息

• Various P∗-chiral phosphite-type ligands: their synthesis, stereochemistry and use in Pd-catalysed allylation
  作者：Eduard B. Benetsky、Sergey V. Zheglov、Tatiana B. Grishina、Fliur Z. Macaev、Liudmila P. Bet、Vadim A. Davankov、Konstantin N. Gavrilov

  DOI：10.1016/j.tetlet.2007.09.125

  日期：2007.11

  available modular phosphite, phosphoramidite and diamidophosphite ligands with P∗-stereocentres have been prepared from inexpensive optically active precursors. Using these novel ligands, up to 91% ee was achieved in Pd-catalysed asymmetric allylic amination. The catalytic performance is affected greatly by the structure of the phosphocentre of the ligand.

  由廉价的光学活性前体制备了一个新的易于获得的，具有P ＊-立体中心的模块化亚磷酸酯，亚磷酰胺和亚酰胺基亚磷酸酯配体。使用这些新颖的配体，在Pd催化的不对称烯丙基胺化反应中可实现高达91％的ee。配体的磷中心的结构极大地影响了催化性能。
• An efficient chiral phosphitooxazoline ligand for Pd-catalyzed asymmetric allylic sulfonylation
  作者：Oleg G. Bondarev、Sergey E. Lyubimov、Alexei A. Shiryaev、Nikolay E. Kadilnikov、Vadim A. Davankov、Konstantin N. Gavrilov

  DOI：10.1016/s0957-4166(02)00371-3

  日期：2002.8

  The new chiral phosphitooxazoline ligand 1 has been synthesized and found to give up to 92% ee in the Pd-catalyzed asymmetric sulfonylation of 1.3-diphenylpropen-2-yl acetate with sodium p-toluenesulfinate. (C) 2002 Elsevier Science Ltd. All rights reserved.
• P,N-Bidentate aryl phosphite ligands based on chiral 2-imino-, 2-oxazolinyl and 2-oxazolidinyl phenols and their catalytic activity
  作者：Konstantin N. Gavrilov、Vasily N. Tsarev、Sergey V. Zheglov、Sergey E. Lyubimov、Alexei A. Shyryaev、Pavel V. Petrovskii、Vadim A. Davankov

  DOI：10.1070/mc2004v014n06abeh002038

  日期：2004.1

  New P,N-hybrid aryl phosphites with distant imino, oxazolino and oxazolidino groups are effective chiral ligands in Pd-catalysed asymmetric allylic substitution reactions.
• Imino‐ and Oxazolino‐Functionalised Pyrrolylphosphanes and Pyrrolylphosphinites: An Unexploited Class of Chiral <i>P,N</i> ‐Bidentate Ligands with Unusual Electronic Properties
  作者：Konstantin N. Gavrilov、Vasily N. Tsarev、Stanislav I. Konkin、Sergey E. Lyubimov、Alexander A. Korlyukov、Mikhail Yu. Antipin、Vadim A. Davankov

  DOI：10.1002/ejic.200500075

  日期：2005.8

  AbstractEnantiopure P,N‐bidentate pyrrolylphosphanes and pyrrolylphosphinites have been prepared based upon chiral imino‐ and oxazolino‐containing compounds. Complexation of the new ligands with [Rh(CO)2Cl]2 and [Pd(allyl)Cl]2 has been found to give the chelate complexes [Rh(CO)Cl(η2‐P,N)] and [Pd(allyl)(η2‐P,N)]+BF4–, respectively. Imino‐ and oxazolino‐functionalised pyrrolylphosphanes and pyrrolylphosphinites have been shown to be a novel class of P,N‐bidentate ligands possessing exceptional π‐acceptor and original σ‐donor properties. With these ligands, up to 77 % ee has been achieved in the asymmetric Pd‐catalyzed sulfonylation of 1,3‐diphenyl‐2‐propenyl acetate with sodium p‐toluenesulfinate. In the enantioselective alkylation of 1,3‐diphenyl‐2‐propenyl acetate with dimethyl malonate, up to 93 % enantioselectivity has been achieved by using [Pd(allyl)(η2‐P,N)]+BF4– complexes as chiral catalysts. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)