(1S)-2-methyl-1-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propylamine | 1224373-71-0

• 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: (1S)-2-methyl-1-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propylamine
• 英文别名: (2S)-2-methyl-1-((4S)-4-phenyl-4,5-dihydro-oxazol-2-yl)propylamine；(S)-2-methyl-1-((S)-4-phenyl-4,5-dihydrooxazol-2-yl)propan-1-amine
• CAS: 1224373-71-0
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: MMYQJGIYIXXMHQ-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S)-2-methyl-1-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propylamine 、 3,4-二甲氧基-3-环丁烯-1,2-二酮 以 甲醇 为溶剂， 反应 4.0h， 以74%的产率得到3,4-bis((S)-1-((S)-4,5-dihydro-4-phenyloxazol-2-yl)-2-methylpropylamino)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Enantioselective Friedel–Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline–Zn(OTf)2 complexes

  摘要：

  Enantioselective Friedel-Crafts alkylation reactions of indoles with beta,gamma-unsaturated alpha-ketoesters catalyzed by novel chiral C-2-symmetric squaramide-linked bisoxazoline-Zn(OTf)(2) complexes were investigated. The corresponding indole ketoesters were obtained in good to excellent yields (up to 98%) and with high enantioselectivities (up to 94% ee). This is the first report on the use of chiral squaramide-linked bisoxazoline SQBOX in a catalytic enanitioselective Friedel-Crafts alkylation reaction. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.05.011
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (1S)-2-methyl-1-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propylamine
  参考文献：
  名称：

  CuI催化的含膦基-恶唑啉配体的（E）-硝基烯烃和环烯酮的对映体选择性1,4-烷基

  摘要：

  已开发出新的膦基-恶唑啉配体，该配体已被用于铜催化的（E）-硝基烯烃的铜对映体选择性共轭加成反应。

  DOI：

  10.1002/ejoc.201800476

文献信息

• Direct synthesis of anthracenes from o-tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp C H arylation and electrophilic aromatic cyclization
  作者：Hyojin Park、Kwangho Yoo、Byunghyuck Jung、Min Kim

  DOI：10.1016/j.tet.2018.03.006

  日期：2018.4

  The first direct synthesis of substituted anthracenes from o-tolualdehydes and aryl iodides via a Pd(II)-catalyzed CH arylation using an alcohol-bearing transient directing group and subsequent AgOTf-assisted electrophilic aromatic cyclization is described. New transient directing groups consisting of amino acids and amino alcohols enhanced the reactivity, and the CH arylation was complete in 12 h

  描述了由邻甲苯甲醛和芳基碘化物通过Pd（II）催化的C H芳基化反应，使用含醇的瞬态直接基团和随后的AgOTf辅助的亲电芳族环化反应，直接合成取代的蒽。由氨基酸和氨基醇组成的新的瞬态导向基团增强了反应活性，并且在90°C下12 h内C H芳基化反应完成。通过简单地将银盐改变为三氟甲磺酸银，使用本反应条件进行蒽衍生物的一锅合成。
• Synthesis of novel chiral oxazoline-Schiff base ligands for the catalytic asymmetric chlorination of β-keto esters
  作者：Ming-Hui Qi、Fei-Jun Wang、Min Shi

  DOI：10.1016/j.tetasy.2010.02.003

  日期：2010.2

  A series of novel monooxazoline-Schiff base ligands 1 has been successfully synthesized. The Cu(I)–1a complex showed excellent catalytic activities with up to 83% ee for the asymmetric α-chlorination of β-keto esters.

  已成功合成了一系列新型的单恶唑啉-席夫碱配体1。Cu（I）–1a络合物显示出优异的催化活性，对β-酮酸酯的不对称α-氯化反应，ee高达83％。
• Cu^I -Catalysed Enantioselective Alkyl 1,4-Additions to (<i>E</i> )-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands
  作者：Minkyeong Shin、Minji Gu、Sung Soo Lim、Min-Jae Kim、JuHyung Lee、HyeongGyu Jin、Yun Hee Jang、Byunghyuck Jung

  DOI：10.1002/ejoc.201800476

  日期：2018.6.29

  New phosphino‐oxazoline ligands have been developed, and the ligands have been used for Cu‐catalysed enantioselective conjugate additions to (E)‐nitroalkenes.

  已开发出新的膦基-恶唑啉配体，该配体已被用于铜催化的（E）-硝基烯烃的铜对映体选择性共轭加成反应。
• Enantioselective Friedel–Crafts alkylation of indoles with β,γ-unsaturated α-ketoesters catalyzed by new squaramide-linked bisoxazoline–Zn(OTf)2 complexes
  作者：Sheng-Jian Jia、Da-Ming Du

  DOI：10.1016/j.tetasy.2014.05.011

  日期：2014.7

  Enantioselective Friedel-Crafts alkylation reactions of indoles with beta,gamma-unsaturated alpha-ketoesters catalyzed by novel chiral C-2-symmetric squaramide-linked bisoxazoline-Zn(OTf)(2) complexes were investigated. The corresponding indole ketoesters were obtained in good to excellent yields (up to 98%) and with high enantioselectivities (up to 94% ee). This is the first report on the use of chiral squaramide-linked bisoxazoline SQBOX in a catalytic enanitioselective Friedel-Crafts alkylation reaction. (C) 2014 Elsevier Ltd. All rights reserved.