(S)-4-isopropyl-2-(naphthalen-1-yl)-4,5-dihydro-1,3-oxazole | 132912-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4-isopropyl-2-(naphthalen-1-yl)-4,5-dihydro-1,3-oxazole
• 英文别名: (S)-4-isopropyl-2-(naphthalen-1-yl)-4,5-dihydrooxazole；(4S)-2-naphthalen-1-yl-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 132912-18-6
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: BOUPXYXHWKSTJU-OAHLLOKOSA-N

物化性质

• 沸点：
  385.7±11.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-2-(naphthalen-1-yl)-4,5-dihydro-1,3-oxazole 在 四丁基氟化铵 、 lithium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 (S)-2-((S)-1-Allyl-1,2-dihydro-naphthalen-1-yl)-4-isopropyl-4,5-dihydro-oxazole
  参考文献：
  名称：

  Asymmetric Synthesis of 1,1-Disubstituted Tetralins and Dihydronaphthalenes by Diastereoselective Addition of Lithiosilanes to Chiral Naphthalenes

  摘要：

  Highly diastereoselective additions of lithiosilanes to chiral naphthalenes can be performed in ether/THF. Trapping of the resulting azaenolate, followed by protodesilylation, allows access to 1,1-disubstituted tetralins or dihydronaphthalenes in good yields and high enantiomeric excess.

  DOI：

  10.1021/jo00084a007
• 作为产物：
  描述：

  1-萘基三氟甲磺酸酯 在 palladium diacetate 、 氯化亚砜 、 1,3-双(二苯基膦)丙烷 、 三乙胺 作用下， 反应 1.0h， 生成 (S)-4-isopropyl-2-(naphthalen-1-yl)-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  通过三氟甲磺酸和钯催化的CO和氨基醇偶联反应从酮和丙醇合成手性α，β-不饱和和芳基恶唑啉

  摘要：

  使用酮和酚的三氟甲磺酸酯，然后在手性氨基醇存在下，Pd催化的CO插入，可以实现标题化合物的有效途径。芳基，乙烯基溴化物和2-吡啶酮也用作有用的底物。

  DOI：

  10.1016/s0040-4039(00)91890-2

文献信息

• New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes
  作者：Rym Hassani、Mahjoub Jabli、Yakdhane Kacem、Jérôme Marrot、Damien Prim、Béchir Ben Hassine

  DOI：10.3762/bjoc.11.132

  日期：——

  the synthesis of new palladium-oxazoline complexes in one step with good to high yields (68-95%). The oxazolines were prepared from enantiomerically pure alpha-aminoalcohols. The structures of the synthesized palladium complexes were confirmed by NMR, FTIR, TOFMS, UV-visible spectroscopic analysis and X-ray diffraction. The optical properties of the complexes were evaluated by the determination of the

  本文描述了一种新的钯-恶唑啉配合物的合成方法，该方法具有良好的收率（68％至95％）。恶唑啉由对映体纯的α-氨基醇制备。合成的钯配合物的结构通过NMR，FTIR，TOFMS，UV-可见光谱分析和X射线衍射确认。通过确定在2.34和3.21eV之间的能隙值（E g）来评估络合物的光学性质。在生态氧化剂（H2O2）存在下，测试了它们的催化活性对Eriochrome Blue Black B（偶氮染料的模型）的降解。脱色的效率已经通过紫外可见光谱分析得到了证实，并且已经研究了影响降解现象的因素。去除铬铬铁合金的收率很高。我们发现，配合物9在5分钟内（C 0 = 30 mg / L，T = 22摄氏度，pH 7，H2O2 = 0.5 mL）促进了84％的消色，并且还确定了能量参数。
• Highly reactive organolithiums (from “Freeman's Reagent”) and their additions to naphthalene oxazolines.
  作者：David J. Rawson、A.I. Meyers

  DOI：10.1016/s0040-4039(00)71245-7

  日期：1991.5

  Generation of organolithium reagents using lithio ditert-butyl biphenyl (Freeman's Reagent) leads to facile additions to the naphthalene oxazolines.

  使用硫代二叔丁基联苯（Freeman试剂）生成有机锂试剂可轻松添加到萘恶唑啉中。
• Efficacious and rapid metal- and solvent-free synthesis of enantiopure oxazolines
  作者：Rym Hassani、Alexandre Requet、Sylvain Marque、Anne Gaucher、Damien Prim、Yakdhane Kacem、Béchir Ben Hassine

  DOI：10.1016/j.tetasy.2014.08.010

  日期：2014.10

  A rapid and efficient synthesis of oxazolines was performed starting from various nitriles using microwave irradiation combined to metal- and solvent-free conditions to afford high to quantitative yields of the targeted heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.
• Asymmetric tandem additions to chiral naphthyloxazolines. A new and potent chiral auxiliary resulting in a major improvement in convenience and efficiency
  作者：David J. Rawson、A. I. Meyers

  DOI：10.1021/jo00007a010

  日期：1991.3

  Excellent diastereofacial selectivities over a wide range of temperatures (-78 to 25-degrees-C) were obtained with the title compounds with use of chiral oxazolines derived from (S)-valinol or (S)-tert-leucinol. These are the first useful levels of asymmetric induction observed without the presence of the chelating methoxyl groups. The dihydronaphthylcarbinols and aldehydes resulting from these additions were obtained in > 98% ee.
• RAWSON, DAVID J.;MEYERS, A. I., J. ORG. CHEM., 56,(1991) N, C. 2292-2294
  作者：RAWSON, DAVID J.、MEYERS, A. I.

  DOI：——

  日期：——