(S)-4-benzyl-2-(2-fluorophenyl)-4,5-dihydrooxazoline | 150255-46-2

• 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)-4-benzyl-2-(2-fluorophenyl)-4,5-dihydrooxazoline
• 英文别名: (4S)-4-Benzyl-2-(2-fluorophenyl)-4,5-dihydro-1,3-oxazole
• CAS: 150255-46-2
• 化学式: C₁₆H₁₄FNO
• 分子量: 255.292
• InChiKey: DLOMMWMYZPIYHQ-ZDUSSCGKSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  381.6±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基二苯硫醚 、 (S)-4-benzyl-2-(2-fluorophenyl)-4,5-dihydrooxazoline 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.33h， 以45.5%的产率得到
  参考文献：
  名称：

  Tridentate diarylamido-based pincer complexes of nickel and palladium: sidearm effects in the polymerization of norbornene

  摘要：

  在新的二芳胺基不对称喹啉[NNN^ox]和苯硫基[SNN^ox]钳型配体催化的Ni和Pd络合物催化剂下，发现了侧臂效应，这些催化剂用于聚合诺邦烯。

  DOI：

  10.1039/c9dt02361e
• 作为产物：
  描述：

  N-[(1S)-1-benzyl-2-hydroxyethyl]-2-fluorobenzamide 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(S)-4-benzyl-2-(2-fluorophenyl)-4,5-dihydrooxazoline
  参考文献：
  名称：

  新型铁膦恶唑啉配合物的合成与结构表征

  摘要：

  合成了铁的第一膦氧恶唑啉螯合物，并研究了它们的结构和电子性质。

  DOI：

  10.1016/j.jorganchem.2008.06.031

文献信息

• Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines
  作者：Markus Peer、Johannes C. de Jong、Matthias Kiefer、Thomas Langer、Heiko Rieck、Heico Schell、Peter Sennhenn、Jürgen Sprinz、Henning Steinhagen、Burkhard Wiese、Günter Helmchen

  DOI：10.1016/0040-4020(96)00267-0

  日期：1996.5

  synthetic amino alcohols. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid, (ii) ZnCl2 catalyzed condensation with a 2-halobenzonit-rile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines containing stereogenic phosphorus were prepared by either diastereoselective nucleophilic substitution of halogenide

  由市售或合成的氨基醇制备一系列对映体纯的2- [2-（二芳基膦基）芳基]-恶唑啉。对于恶唑啉的形成，采用了三种程序：（i）与2-卤代苯甲酸一锅缩合，（ii）ZnCl 2与2-卤代苯甲腈-苯胺催化缩合，和（iii）通过2-卤代苯甲酰胺的三步顺序和甲苯磺酸盐或氯化物。通过非对映选择性亲核取代Ar 1 Ar 2 PC1的卤化物或通过LiPAr 1 Ar 2亲核芳族取代制备含有立体异构磷的膦恶唑啉。另外，制备了硫和硒类似物。
• Preparation of novel Sulfur and phosphorus containing oxazolines as ligands for asymmetric catalysis
  作者：Joanne V. Allen、Graham J. Dawson、Christopher G. Frost、Ionathan M.J. Williams、Steven J. Coote

  DOI：10.1016/s0040-4020(01)80795-x

  日期：1994.1

  The preparation of enantiomerically pure liginds which contain both an oxazoline group and an additional sulfur or phosphorus donor atom are described. Methyithiomethyl, o-thioanisyl and thienyl oxazolines have been prepared in one step, and o-diphenylphosphinophenyl oxazolines have been prepared in two steps in good yields from commercially available starting materials.

  描述了同时包含恶唑啉基团和另外的硫或磷供体原子的对映体纯的配体的制备。一步法制得了甲硫基甲基，邻硫代茴香基和噻吩基恶唑啉，并分两步从可商购的起始原料中以高收率制备了邻二苯基膦基苯基恶唑啉。
• Synthesis of nickel and palladium complexes with diarylamido-based unsymmetrical pincer ligands and application for norbornene polymerization
  作者：Hui Liu、Haibin Yuan、Xiaochao Shi

  DOI：10.1039/c8dt04413a

  日期：——

  M = Ni (Ni3); R1 = 4-Me, R = (S)-4-Ph, M = Pd (Ni4)) were tested to show high catalytic activities for polymerization of norbornene. After activation of methylaluminoxane (MAO), all the nickel and palladium complexes could catalyze the polymerization of norbornene to yield vinyl-type polymers with activities up to 40.3 × 105 g of PNB (mol of Pd)−1 h−1. The copolymerization of norbornene with functional

  合成了一组含有手性恶唑啉环的基于二芳基酰胺基的不对称[PNN ox ]钳位配体，它们的镍和钯配合物[（2-PPh 2（R 1）ArN（R 1）Ar-2-（R）恶唑啉） ）MCl]（R 1 = 4-H，R =（S）-4- i Pr，M = Pd（Pd1）; R 1 = 4-H，R =（S）-4-Bn，M = Pd（Pd2）; R 1 = 4-H，R =（S）-4-Ph，M = Pd（Pd3）; R 1 = 4-Me，R =（S）-4-Bn，M = Pd（Pd4） ； R 1 = 4-Me，R =（S）-4-Ph，M = Pd（Pd5）; R 1 = 4-H，R = 4-Me 2，M = Pd（Pd6）；R 1 = 4-H，R =苯并[ d ]-，M = Pd（Pd7）；R 1 = 4-H，R =（S）-4-Bn，M = Ni（Ni1）; R 1＝ 4-H，R ＝（S）-4-Ph，M ＝ Ni（Ni
• Palladium-Catalyzed C-2 C–H Heteroarylation of Chiral Oxazolines: Diverse Synthesis of Chiral Oxazoline Ligands
  作者：Tuo Xi、Yuncai Mei、Zhan Lu

  DOI：10.1021/acs.orglett.5b03041

  日期：2015.12.18

  A direct, efficient, and practical protocol to install a chiral Oxazoline unit onto aryl/heteroaryl rings via palladium-catalyzed C-H functionalization of 2-positions of oXazolines with a variety of halides using dppe as the ligand has been developed. Various chiral oxazdline ligands could be synthesized, even in a 10-g scale process. This protocol is a good supplement to traditional methods and for diverse synthesis of chiral oxazoline ligands.
• In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination
  作者：David B. Berkowitz、Weijun Shen、Gourhari Maiti

  DOI：10.1016/j.tetasy.2004.06.052

  日期：2004.9

  An in situ enzymatic screening (ISES) approach to rapid catalyst evaluation recently pointed to Ni(0) as a new candidate transition metal for intramolecular allylic amination. This led to further exploration of chiral bidentate phosphine ligands for such transformations. Herein, a variety of P,N-ligands are examined for this Ni(0)-chemistry, using a model reaction leading into the vinylglycinol scaffold. On the one hand, an N,N-bis(2-diphenylphosphinoethyl)alkylamine ('PNP') ligand proved to be the fastest ligand yet seen for this Ni(0)-transformation. On the other, phosphinooxazoline (PHOX) ligands of the Pfaltz-Helmchen-Williams variety gave the highest enantioselectivities (up to 51% ee) among P,N-ligands examined. (C) 2004 Elsevier Ltd. All rights reserved.