(S)-2-ethoxy-4,5-dihydro-4-(1-methylethyl)oxazole | 102922-29-2

• 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)-2-ethoxy-4,5-dihydro-4-(1-methylethyl)oxazole
• 英文别名: (S)-ethoxyoxazoline；(S)-2-ethoxy-4-isopropyl-4,5-dihydrooxazole；(S)-2-ethoxy-4-isopropyl-4,5-dihydrooxazol；(4S)-2-ethoxy-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 102922-29-2
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: WZNNUOMFTWRPQS-SSDOTTSWSA-N

物化性质

• 沸点：
  59 °C(Press: 2.5 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-ethoxy-4,5-dihydro-4-(1-methylethyl)oxazole 在 对甲苯磺酸 叔丁基锂 、 对甲苯磺酸 、 一水合肼 作用下， 以 乙醇 、 苯 为溶剂， 反应 10.33h， 生成 L-缬氨醇
  参考文献：
  名称：

  Chiral dipole-stabilized anions: experiment and theory in benzylic and allylic systems. Stereoselective deprotonations, pyramidal inversions, and stereoselective alkylations of lithiated (tetrahydroisoquinolyl)oxazolines

  摘要：

  DOI：

  10.1021/ja00188a040
• 作为产物：
  描述：

  L-缬氨醇 在 sodium ethanolate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S)-2-ethoxy-4,5-dihydro-4-(1-methylethyl)oxazole
  参考文献：
  名称：

  Chiral dipole-stabilized anions: experiment and theory in nonbenzylic systems. 100 Percent stereoselective deprotonation and two-electron versus single-electron transfer in the chemistry of lithium and copper piperidinooxazolines

  摘要：

  DOI：

  10.1021/jo00262a039

文献信息

• Synthesis and Pharmacological Activity of Alkaloids from Embryo of Lotus, <i>Nelumbo nucifera</i>
  作者：Katsumi Nishimura、Shinji Horii、Takao Tanahashi、Yumi Sugimoto、Jun Yamada

  DOI：10.1248/cpb.c12-00820

  日期：——

  Bisbenzylisoquinoline alkaloid, nelumboferine which was recently isolated from the embryo of Nelumbo nucifera, and stereoisomers of neferine, which is a major alkaloid of the embryo of N. nucifera, were stereoselectively synthesized. Pharmacological activity of nelumboferine, stereoisomers of neferine, liensinine, isoliensinine, and O-methylneferine were evaluated.

  立体选择性地合成了双苄基异喹啉生物碱，最近从睡莲的胚中分离出的睡莲碱和睡莲的立体异构体，其是睡莲胚的主要生物碱。评估了肾上腺素，肾上腺素的立体异构体，莲心碱，异莲心碱和O-甲基肾上腺素的药理活性。
• Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds
  作者：Bob Gawley、Robert E. Gawley、Gregory A. Smith

  DOI：10.3998/ark.5550190.0012.514

  日期：——

  Asymmetric alkylation of enantiomeric tetrahydroisoquinolyl oxazolines was achieved with 96-97% diastereoselectivity. Removal of the oxazoline chiral auxiliary and further transformations provide a straightforward synthesis of the two synthetic intermediates that were previously synthesized by resolution, and which comprise a formal synthesis of berbamunine by Ullman coupling.

  对映体四氢异喹啉恶唑啉的不对称烷基化以 96-97% 的非对映选择性实现。恶唑啉手性助剂的去除和进一步的转化提供了先前通过拆分合成的两种合成中间体的直接合成，它们包括通过乌尔曼偶联正式合成小檗碱。
• Improved Synthesis of Aza-bis(oxazoline) Ligands
  作者：Heiko Werner、Robert Vicha、Anja Gissibl、Oliver Reiser

  DOI：10.1021/jo0350920

  日期：2003.12.1

  A straightforward synthesis of chiral aza-bis(oxazoline) (Azabox) ligands from commercially available amino alcohols is described. The new protocol allows access to previously reported Azabox ligands in considerably improved yields but also to new derivatives, including non-C2-symmetrical ones.

  描述了由市售氨基醇直接合成手性氮杂双（恶唑啉）（Azabox）配体。新方案允许以大大提高的产率获得先前报道的Azabox配体，但也可以获得新的衍生物，包括非C2对称​​的衍生物。
• Stereoselectivity induced by support confinement effects. Aza-pyridinoxazolines: A new family of C1-symmetric ligands for copper-catalyzed enantioselective cyclopropanation reactions
  作者：José I. García、Gonzalo Jiménez-Osés、Beatriz López-Sánchez、José A. Mayoral、Andrea Vélez

  DOI：10.1039/b919274c

  日期：——

  Aza-pyridinoxazoline ligands, a new class of C1-symmetric ligands, are described and tested in the heterogeneous enantioselective catalysis of a cyclopropanation reaction, with the aim of improving surface confinement effects by the clay support on the reaction stereoselectivity. In the case of trans/cis diastereoselectivity, these surface effects lead to a systematic reversal of selectivity, cis-cyclopropanes

  阿扎--吡啶并恶唑啉在环丙烷化反应的多相对映选择性催化中描述并测试了一种新型的C 1对称配体，以改善粘土载体对反应立体选择性的表面限制作用。在反式/顺式非对映选择性的情况下，这些表面效应导致选择性的系统逆转，顺式-环丙烷是有利的。关于对映选择性，在大范围情况下，支持限制具有积极作用顺式环丙烷产品，导致中等的对映选择性值（60％ee）。进行了理论（DFT）机理研究，以解释分子水平上均相中对映选择性的起源，并获得了关键中间体和过渡结构的几何形状的见解。
• Development of Bifunctional Aza-Bis(oxazoline) Copper Catalysts for Enantioselective Henry Reaction
  作者：Kai Lang、Jongwoo Park、Sukwon Hong

  DOI：10.1021/jo1009867

  日期：2010.10.1

  Base-functionalized aza-bis(oxazoline) ligands were prepared to explore the concept of dual activation through the Lewis acid and a tethered tertiary amine base, The catalytic activity of the Cu complex was evaluated for the asymmetric Henry reaction. Compared with a corresponding unfunctionalized copper complex with external 1-benzyl-4-ethylpiperazine base, the ethylpiperazine-functionalized aza-bis(oxazoline) copper catalyst resulted in rate acceleration (2.5 times) as well as improved enantioselectivity (72% ee vs 92% ee).