3,5-diphenyl-isoxazolidine | 74726-60-6

• 英文名称: 3,5-diphenyl-isoxazolidine
• 英文别名: 3,5-Diphenyl-isoxazolidin；3,5-Diphenyl-1,2-oxazolidine
• CAS: 74726-60-6
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: FCVIDHGKFVWYKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 羟胺 作用下， 生成 3,5-diphenyl-isoxazolidine
  参考文献：
  名称：

  Kotschetkow; Infant'ew, Doklady Akademii Nauk SSSR, 1958, vol. 121, p. 462,465

  摘要：

  DOI：

文献信息

• Intermolecular Cycloaddition of Ethyl Glyoxylate <i>O-tert</i>-Butyldimethyl­silyloxime with Alkenes
  作者：Osamu Tamura、Hiroyuki Ishibashi、Nobuyoshi Morita、Yuu Takano、Kenji Fukui、Iwao Okamoto、Xin Huang、Yoshiyuki Tsutsumi

  DOI：10.1055/s-2007-967939

  日期：——

  Ethyl glyoxylate O-tert-butyldimethylsilyloxime, on treatment with various alkenes in the presence of BF3·OEt2, ­generated a C-ethoxycarbonyl N-boranonitrone intermediate, which underwent intermolecular cycloaddition to afford 3-(ethoxy­carbonyl)isoxazolidines in moderate to high yields.

  在BF3·OEt2存在下，乙二醛酸O-叔丁基二甲基硅氧基苯胺与各种烯烃反应，生成C-乙氧羰基N-硼烷腈中间体，该中间体经过分子间环加成反应，以中等至高产率得到3-（乙氧羰基）异恶唑烷酮。
• Asymmetric reduction of racemic 2-isoxazolines
  作者：Masashi Tokizane、Kaori Sato、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1016/j.tetasy.2008.11.005

  日期：2008.11

  The kinetic resolution of racemic 2-isoxazolines was carried out by asymmetric reduction using borane with 1,2-amino alcohols as a chiral Source. Using excess BH3-THF in the presence of (-)-norephedrine, optically active 1,3-amino alcohol derivatives were obtained with good ee but in lower yield, while the optically active substrates 2-isoxazolines were recovered with modest ee. The asymmetric reduction using 2.0 equiv of BH3-SMe2 was investigated as an alternative strategy for the synthesis of optically active products. After reduction, treatment of the resulting Mixture with Et3N was successful in providing optically active isoxazolidine derivatives in good yields and with good ee. The choice of chiral source was also shown to have a significant effect. In particular, the use of (S)-alpha,alpha-diphenyl-2-pyrrolidinemethanol reversed the enantioselectivity of the recovered Substrates. (C) 2008 Elsevier Ltd. All rights reserved.