(4S)-2,2-dimethyl-4-phenylmethyloxazolidine | 144899-41-2

• 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-phenylmethyloxazolidine
• 英文别名: (S)-4-benzyl-2,2-dimethyloxazolidine；(4S)-4-benzyl-2,2-dimethyl-1,3-oxazolidine
• CAS: 144899-41-2
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: GAECFGTWXPTWCQ-NSHDSACASA-N

物化性质

• 沸点：
  273.6±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)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-phenylmethyloxazolidine 在 TEA 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 乙腈 作用下， 以 二氯甲烷 为溶剂， 生成 2-benzenesulfonyl-2-diazo-1-(2,2-dimethyl-4-benzyl-oxazolidin-3-yl)-ethanone
  参考文献：
  名称：

  通过Rh（II）催化的分子内C–H插入合成手性γ-内酰胺：α-取代基和构象效应

  摘要：

  高度官能化的手性γ-内酰胺可以通过Rh（II）催化的各种C-H分子内插入各种α-重氮酰胺来合成。独立于α-取代基，通过双环过渡态所产生的构象效应增强了区域选择性和立体选择性。

  DOI：

  10.1016/j.tetlet.2004.10.159
• 作为产物：
  描述：

  L-苯丙氨醇 、 丙酮 在 对甲苯磺酸 作用下， 反应 12.0h， 生成 (4S)-2,2-dimethyl-4-phenylmethyloxazolidine
  参考文献：
  名称：

  New chiral auxiliaries based on conformation control, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral, 2,2-dialkyloxazolidines. Synthesis and conformational analysis of acrylamide derivatives

  摘要：

  New chirality-controlling auxiliaries, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines, are readily prepared from a C2-SYMMetriC 1,2-ethanediamine and naturally occurring alpha-amino acids, respectively. Conformational analysis of their N-acryloyl derivatives has been carried out on the basis of dynamic H-1 NMR spectroscopy and molecular mechanics calculations using MM2 program. Proper choice of the substituents at 2-, 4-, and 5-positions, in the oxazolidine cases, leads to the most effective chiral shielding of a diastereotopic acryloyl face.

  DOI：

  10.1016/s0040-4020(01)89439-4

文献信息

• 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。
• Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues
  作者：Ciarán Ó Dálaigh、Stephen J. Hynes、Declan J. Maher、Stephen J. Connon

  DOI：10.1039/b419335k

  日期：——

  We report the development of a new class of readily prepared chiral 4-(pyrrolidino)-pyridine catalysts capable of exploiting both van der Waals (π) and H-bonding interactions, thus allowing remote chiral information to stereochemically control the kinetic resolution of sec-alcohols.

  我们报道了一种新型易制备的手性4-(吡咯烷基)-吡啶催化剂的开发，该催化剂能够利用范德华（π）和氢键相互作用，从而允许远程手性信息通过立体化学控制仲醇的动态拆分。
• Asymmetric acyl-transfer promoted by readily assembled chiral 4-N,N-dialkylaminopyridine derivatives
  作者：Ciarán Ó. Dálaigh、Stephen J. Hynes、John E. O'Brien、Thomas McCabe、Declan J. Maher、Graeme W. Watson、Stephen J. Connon

  DOI：10.1039/b604632k

  日期：——

  The development of a new class of chiral 4-N,N-dialkylaminopyridine acyl-transfer catalysts capable of exploiting both van der Waals (π) and H-bonding interactions to allow remote chiral information to stereochemically control the kinetic resolution of sec-alcohols with moderate to excellent selectivity (s = 6–30). Catalysts derived from (S)-α,α-diarylprolinol are considerably superior to analogues devoid of a tertiary hydroxyl moiety and possess high activity and selectivity across a broad range of substrates.

  开发了一类新型 4-N,N-二烷基氨基吡啶手性酰基转移催化剂，该催化剂能够利用范德华（π）和氢键相互作用，通过远程手性信息立体化学控制仲醇的动力学解析，并具有中等至卓越的选择性（s = 6-30）。由 (S)-α,α-二芳基脯氨醇衍生的催化剂大大优于没有叔羟基的类似物，并且在广泛的底物中具有高活性和高选择性。
• Klotz-Berendes, Bruno; Schaefer, Hans J.; Grehl, Matthias, Angewandte Chemie, 1995, vol. 107, # 2, p. 218 - 220
  作者：Klotz-Berendes, Bruno、Schaefer, Hans J.、Grehl, Matthias、Froehlich, Roland

  DOI：——

  日期：——
• New chiral auxiliaries based on conformation control, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral, 2,2-dialkyloxazolidines. Synthesis and conformational analysis of acrylamide derivatives
  作者：Shuji Kanemasa、Kenjiro Onimura

  DOI：10.1016/s0040-4020(01)89439-4

  日期：——

  New chirality-controlling auxiliaries, a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines, are readily prepared from a C2-SYMMetriC 1,2-ethanediamine and naturally occurring alpha-amino acids, respectively. Conformational analysis of their N-acryloyl derivatives has been carried out on the basis of dynamic H-1 NMR spectroscopy and molecular mechanics calculations using MM2 program. Proper choice of the substituents at 2-, 4-, and 5-positions, in the oxazolidine cases, leads to the most effective chiral shielding of a diastereotopic acryloyl face.