2-噁唑烷硒酮,4-(1-甲基乙基)-,(4S)- | 136794-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2-噁唑烷硒酮,4-(1-甲基乙基)-,(4S)-
• 英文名称: (S)-4-isopropyl-oxazolidine-2-selone
• 英文别名: (S)-(-)-4-(1-Methylethyl)oxazolidine-2-selone；(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazole-2-selenol
• CAS: 136794-52-0
• 化学式: C₆H₁₁NOSe
• 分子量: 192.119
• InChiKey: KAUCXVYANKLWEM-RXMQYKEDSA-N

物化性质

• 沸点：
  198.6±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  2-苯基丙酰氯 、 2-噁唑烷硒酮,4-(1-甲基乙基)-,(4S)- 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(4S)-3-(1-Oxo-2-phenylpropyl)-4-(1-methylethyl)oxazolidine-2-selone
  参考文献：
  名称：

  An improved synthesis of chiral oxazolidine-2-selones: highly sensitive selenium-77 NMR reagents for the detection and quantitation of chirality

  摘要：

  The synthesis of the title compounds from readily available oxazolines has been accomplished in one step in high yield. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.

  DOI：

  10.1021/jo00024a003
• 作为产物：
  描述：

  (S)-4-isopropyl-4,5-dihydrooxazole 在 selenium 、 lithium diisopropyl amide 作用下， 生成 2-噁唑烷硒酮,4-(1-甲基乙基)-,(4S)-
  参考文献：
  名称：

  An improved synthesis of chiral oxazolidine-2-selones: highly sensitive selenium-77 NMR reagents for the detection and quantitation of chirality

  摘要：

  The synthesis of the title compounds from readily available oxazolines has been accomplished in one step in high yield. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.

  DOI：

  10.1021/jo00024a003

文献信息

• Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids
  作者：Erik Hedenström、Ba-Vu Nguyen、Louis A. Silks

  DOI：10.1016/s0957-4166(02)00172-6

  日期：2002.5

  Several racemic methyl decanoic acids have been synthesised and Successfully resolved in esterification with 1-hexadecanol at a(w)=0.8 in cyclohexane using immobilised Candida rugosa lipase (CRL) as the catalyst. The enantiomeric ratios (E=2.8-68) obtained were surprisingly high even when the methyl group was as remotely located as in 8-methyldecanoic acid (E=25). Interestingly, the lipase shows enantiopreference for the S-enantiomer when the methyl group is located on even numbered carbons i.e. for the 2-,4-,6- and 8-methyldecanoic acids and to the R-enantiomer when the methyl group is located on uneven numbered carbons i.e. for the 3-,5- and 7-methyldecanoic acids. (C) 2002 Published by Elsevier Science Ltd.
• An improved synthesis of chiral oxazolidine-2-selones: highly sensitive selenium-77 NMR reagents for the detection and quantitation of chirality
  作者：Louis A. Silks、Jie Peng、Jerome D. Odom、R. Bruce Dunlap

  DOI：10.1021/jo00024a003

  日期：1991.11

  The synthesis of the title compounds from readily available oxazolines has been accomplished in one step in high yield. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.
• Chiral N-Acetyl Selone-Promoted Aldol Reactions
  作者：Louis A. Silks、David B. Kimball、Duane Hatch、Morgane Ollivault-Shiflett、Ryszard Michalczyk、Eddie Moody

  DOI：10.1080/00397910802419706

  日期：2009.1.28

  The chiral oxazolidineselone functionality was found to be an excellent partner in the stereospecific acetate aldol reaction with aldehydes via the titanium enolates. Good stereocontrol was obtained as determined by NMR spectroscopy. The oxazolidineselone also provided a straightforward way to establish the stereopurity of the coupling reaction through 77Se NMR spectroscopy.
• Peng Jie, Barr Mary E., Ashburn David A., Odom Jerome D., Dunlap R. Bruce+, J. Org. Chem, 59 (1994) N 17, S 4977-4987
  作者：Peng Jie, Barr Mary E., Ashburn David A., Odom Jerome D., Dunlap R. Bruce+

  DOI：——

  日期：——
• Synthesis and Characterization of Chiral Oxazolidine-2-selones: A General One-Step Procedure from Readily Available Oxazolines
  作者：Jie Peng、Mary E. Barr、David A. Ashburn、Jerome D. Odom、R. Bruce Dunlap、Louis A. Silks

  DOI：10.1021/jo00096a048

  日期：1994.8

  The synthesis of a wide variety of chiral oxazolidine-2-selones from readily available 2-oxazolines has been accomplished in one step with yields ranging from 82 to 98%. A mechanistic investigation of the formation of these selones has indicated the presence of intermediate anions which have been characterized by C-13 and Se-77 NMR spectroscopy. X-ray crystallographic data suggest the chiral selones exists as dimeric pairs or networks linked by unusual selenium hydrogen bonds. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful fdr the detection and quantitation of chirality at remotely disposed chiral centers.