(4S)-2,2-dimethyl-4-phenyloxazolidine | 112068-78-7

• 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: (4S)-2,2-dimethyl-4-phenyloxazolidine
• 英文别名: (S)-2,2-dimethyl-4-phenyloxazolidine；(4S)-2,2-dimethyl-4-phenyl-1,3-oxazolidine
• CAS: 112068-78-7
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: JWUVAPHBWUUXQE-SNVBAGLBSA-N

物化性质

• 沸点：
  263.3±28.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-2,2-dimethyl-4-phenyloxazolidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  表面选择性添加到吡啶盐的阳离子-π 络合物：手性 1,4-二氢吡啶的合成

  摘要：

  通过分子内阳离子-π 复合物形成选择性屏蔽吡啶鎓面的一侧，使亲核试剂仅从非屏蔽侧进行攻击，因此，手性 1,4-二氢吡啶以高达 99% 的 de 立体选择性产生。通过 1 H NMR 研究和 X 射线分析阐明了阳离子-pi 复合物的结构。

  DOI：

  10.1021/ja0203317
• 作为产物：
  描述：

  L-苯甘氨醇 、 丙酮 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 (4S)-2,2-dimethyl-4-phenyloxazolidine
  参考文献：
  名称：

  Control of stereochemistry in free radical reactions with oxazolidine auxiliaries

  摘要：

  DOI：

  10.1021/ja00020a066

文献信息

• Asymmetric anti-selective aldol reactions of titanium Z-enolates derived from N-alkylideneglycinamides bearing a 2,2-dimethyloxazolidine chiral controller
  作者：Shuji Kanemasa、Takashi Mori、Akira Tatsukawa

  DOI：10.1016/s0040-4039(00)61414-4

  日期：1993.12

  Asymmetric aldol reactions of titanium Z-enolates of N-diphenylmethylene derivatives of glycinamides derived from (4S)-2,2-dimethyloxazolidine chiral auxiliaries are highly ul,ul-1,4-inductive. Hydrolytic removal of the chiral auxiliary from the aldol adducts provide optically active anti-isomers of alpha-amino-beta-hydroxy acids with 2R-absolute configuration.
• Opposite π-Face Selectivity for the DMD and <i>m</i>-CPBA Epoxidations of Chiral 2,2-Dimethyloxazolidine Derivatives of Tiglic Amides:  Control by Steric Interactions versus Hydrogen Bonding
  作者：Waldemar Adam、Aurelia Pastor、Karl Peters、Eva-Maria Peters

  DOI：10.1021/ol990405s

  日期：2000.4.1

  A high extent but opposite sense in the diastereoselectivity has been observed for the DMD and m-CPBA epoxidations of the optically active tiglic amides (S)-1 with 2,2-dimethyloxazolidines as chiral auxiliaries, This unprecedented reversed pi-facial differentiation for these two peroxidic oxidants is rationalized in terms of like (lk) and unlike (ul) transition structures: For DMD, steric interactions dominate, such that the unlike transition structure is favored, while for m-CPBA, hydrogen bonding effects overcome these steric repulsions and the like one is preferred.
• Asymmetric Synthesis of Activated α-Amino Esters via Chromium Carbene Complex Photochemistry
  作者：Jiawang Zhu、Christopher Deur、Louis S. Hegedus

  DOI：10.1021/jo9709817

  日期：1997.10.1

  Optically active chromium aminocarbene complexes were alpha-alkylated and then photolyzed in the presence of 2,4,5-trichlorophenol to produce a number of optically active activated alpha-amino esters. These underwent coupling with amino acid esters or a soluble PEG-supported dipeptide to introduce the chromium-carbene-complex-derived amino acid residue into the peptide.
• Face-Selective Addition to a Cation−π Complex of a Pyridinium Salt:  Synthesis of Chiral 1,4-Dihydropyridines
  作者：Shinji Yamada、Chisako Morita

  DOI：10.1021/ja0203317

  日期：2002.7.1

  Selective shielding of one side of the pyridinium face by way of intramolecular cation-pi complex formation enabled nucleophiles to attack only from the non-shielded side, and consequently, chiral 1,4-dihydropyridines were produced stereoselectively with up to 99% de. The structure of the cation-pi complex was elucidated by 1H NMR studies and X-ray analysis.

  通过分子内阳离子-π 复合物形成选择性屏蔽吡啶鎓面的一侧，使亲核试剂仅从非屏蔽侧进行攻击，因此，手性 1,4-二氢吡啶以高达 99% 的 de 立体选择性产生。通过 1 H NMR 研究和 X 射线分析阐明了阳离子-pi 复合物的结构。
• Control of stereochemistry in free radical reactions with oxazolidine auxiliaries
  作者：Ned A. Porter、John D. Bruhnke、Wen Xue Wu、Ian J. Rosenstein、Robert A. Breyer

  DOI：10.1021/ja00020a066

  日期：1991.9