(S)-4-tert-butyl-2-methyl-Δ²-oxazoline | 137542-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (S)-4-tert-butyl-2-methyl-Δ²-oxazoline
• 英文别名: (4S)-4-tert-butyl-2-methyl-2-oxazoline；(S)-4-tert-butyl-2-methyl-2-oxazoline；(s)-4-t-Butyl-2-methyl-2-oxazoline；(4S)-4-tert-butyl-2-methyl-4,5-dihydro-1,3-oxazole
• CAS: 137542-74-6
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: HXVCLXDGKGJBRY-SSDOTTSWSA-N

物化性质

• 沸点：
  153-154 °C
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (S)-4-tert-butyl-2-methyl-Δ²-oxazoline 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 44.0h， 生成 (4S)-4-tert-butyl-2-<(E)-2-(2-methoxyphenyl)ethenyl>-2-oxazoline
  参考文献：
  名称：

  Asymmetric Michael additions to .alpha.,.beta.-unsaturated oxazolines. An efficient preparation of chiral .beta.,.beta.-disubstituted propionaldehydes

  摘要：

  A short stereoselective route to a variety of chiral, nonracemic alpha,beta-unsaturated oxazolines derived from (S)-tert-leucinol is described. Addition of organolithium reagents to this chiral oxazoline occurs in a Michael fashion, giving rise to adducts with high diastereoselectivity. Reductive cleavage of the oxazoline leaves the beta,beta-disubstituted aldehydes in > 93% ee. This process represents a significant improvement in one of the earliest asymmetric conjugate additions first reported in 1975.

  DOI：

  10.1021/jo00025a027
• 作为产物：
  描述：

  原乙酸三甲酯 、 L-叔亮氨醇 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以87%的产率得到(S)-4-tert-butyl-2-methyl-Δ²-oxazoline
  参考文献：
  名称：

  An Efficient and Versatile Method for the Synthesis of Optically Active 2-Oxazolines: An Acid-catalyzed Condensation of Ortho Esters with Amino Alcohols

  摘要：

  DOI：

  10.1021/jo971161x
• 作为试剂：
  描述：

  三甲基氯硅烷 、 2-环戊烯酮 、 Dimethylzinc 、 三甲基乙炔基硅 在 bis(acetylacetonate)nickel(II) 、 (S)-4-tert-butyl-2-methyl-Δ²-oxazoline 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 (R)-1-Trimethylsilanyloxy-3-((E)-2-trimethylsilanyl-propenyl)-cyclopentene 、 (S)-1-Trimethylsilanyloxy-3-((E)-2-trimethylsilanyl-propenyl)-cyclopentene
  参考文献：
  名称：

  Nickel-Catalyzed Asymmetric Multiple-Component Tandem Coupling. Effects of Simple Monodentate Oxazolines as Chiral Ligands

  摘要：

  DOI：

  10.1021/ja9844231

文献信息

• Lewis Acid-Catalyzed Asymmetric Diels&amp;ndash;Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives
  作者：Kazuhiro Watanabe、Takashi Hirasawa、Kunio Hiroi

  DOI：10.1248/cpb.50.372

  日期：——

  New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels-Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels-Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.

  已开发出新的手性亚砜-1,3-恶唑啉配体作为路易斯酸催化的不对称Diels-Alder反应的手性配体。在铜（II）催化的不对称Diels-Alder反应中使用手性亚磺酰基1,3-恶唑啉配体可提供内环加合物作为主要产物，具有中等对映选择性。提出了不对称感应机理的基本原理。
• Cyclopalladation of (<i>S</i>)-4-<i>tert</i>-Butyl-2-methyl-2-oxazoline:  An Unprecedented Case of (sp³)C−H Bond Activation Resulting in <i>e</i><i>xo</i>-Palladacycle Formation
  作者：Kristopher J. Keuseman、Irina P. Smoliakova、Valery V. Dunina

  DOI：10.1021/om050341r

  日期：2005.8.1

  group using palladium(II) acetate in acetic acid afforded the first example of an oxazoline-derived exo-palladacycle with an (sp3)C−Pd bond. The structure of the new palladacycle was established using spectroscopic and X-ray studies of the μ-chloro-dimeric complex 2 and two mononuclear triphenylphosphane derivatives:  neutral adduct 4 and its cationic benzonitrile-phosphane analogue 5. Analysis of

  （直接cyclopalladation小号）-4-叔丁基-2-甲基-2-恶唑啉在未活化叔丁基使用组钯（II）乙酸在乙酸，得到的恶唑啉衍生的第一示例外型-palladacycle与（sp 3）C-Pd键。新的palladacycle的结构是使用μ-氯-二聚配合物2和两个单核三苯基膦衍生物：中性加合物4及其阳离子苄腈-膦类似物5的光谱和X射线研究建立的。化合物4和5的NMR数据分析表明，λ（S）溶液中的palladacycle构象。阳离子配合物5的X射线晶体结构证实了其在固体状态下具有高度折叠的Palladacycle的λ（S）构象。此外，它揭示了苄腈和PPh 3配体的苯环之间异常的π-π相互作用以及PPh 3片段的扭曲的M-螺旋结构。
• New synthesis of β-amino acids by nucleophilic addition of enolate anions to N-methoxycarbonylimines generated from α-methoxy carbamates1
  作者：Tatsuya Shono*、Naoki Kise、Fumio Sanda、Satoru Ohi、Kenji Tsubata

  DOI：10.1016/s0040-4039(00)80062-3

  日期：1988.1
• Novel strategy for the synthesis of fluorinated β-amino acid derivatives from Δ2-oxazolines
  作者：Santos Fustero、Esther Salavert、Belén Pina、Carmen Ramı́rez de Arellano、Amparo Asensio

  DOI：10.1016/s0040-4020(01)00539-7

  日期：2001.7

  Racemic and chiral non-racemic beta -fluoroalkyl-beta -amino acid derivatives have been prepared in two steps starting from 2-alkyl-Delta (2)-oxazolines and fluorinated imidoyl chlorides. Subsequent chemoselective reduction of the C-masked beta -enamino acid derivatives initially formed provided the target beta -amino acids. The process takes place with total chemoselectivity, high yields and satisfactory diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Watanabe, Kazuhiro; Hirasawa, Takashi; Hiroi, Kunio, Heterocycles, 2002, vol. 58, p. 93 - 97
  作者：Watanabe, Kazuhiro、Hirasawa, Takashi、Hiroi, Kunio

  DOI：——

  日期：——