(4S,5S)-2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline | 54623-66-4

• 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,5S)-2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline
• 英文别名: (4S,5S)-2-(chloromethyl)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 54623-66-4
• 化学式: C₁₂H₁₄ClNO₂
• 分子量: 239.702
• InChiKey: XGHTZLYBINKALZ-JQWIXIFHSA-N

物化性质

• 沸点：
  323.7±37.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline 在 二乙基异丙基胺 作用下， 以 乙醚 为溶剂， 生成 2-chloro-2-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-1-phenylethanol
  参考文献：
  名称：

  Azaenolates of 2-Chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline − A Highly Diastereo- and Enantioselective Synthesis of Oxazolinyloxiranes

  摘要：

  The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.

  DOI：

  10.1002/1099-0690(200106)2001:11<2035::aid-ejoc2035>3.0.co;2-r
• 作为产物：
  描述：

  (4S,5S)-(-)-4-甲氧甲基-2-甲基-5-苯基-2-恶唑啉 生成 (4S,5S)-2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline
  参考文献：
  名称：

  从手性2-氯甲基恶唑啉的氮杂酸酯类高度立体选择性合成旋光性恶唑啉基恶唑烷

  摘要：

  发现旋光性氯甲基恶唑啉1分别在0°C和-100°C生成的硼和氮杂钛酸2和4与脂族酮以非对映选择性的方式偶合，最终形成旋光性恶唑啉基肟3。较少的立体选择性是与芳族酮的反应。

  DOI：

  10.1016/s0040-4039(00)00809-1

文献信息

• Synthesis of Optically Active 2-Chloromethyl-2-oxazolines by the Ortho-ester Codensation Method Using Triethyl Orthochloroacetate
  作者：Kazuyuki Kamata、Hideki Sato、Emi Takagi、Isao Agata、A. I. Meyers

  DOI：10.3987/com-98-8407

  日期：——

  A set of optically active 2-chloromethyl-2-oxazolines was synthesized by condensation of optically active 2-amino alcohols with triethyl orthochloroacetate which was prepared conveniently from triethyl orthoacetate by chlorination using tert-butyl hypochlorite.
• On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds
  作者：Saverio Florio、Vito Capriati、Renzo Luisi、Alessandro Abbotto、Daniel J Pippel

  DOI：10.1016/s0040-4020(01)00611-1

  日期：2001.7

  Optically pure chloromethyloxazolines have been prepared, lithiated and then reacted with benzophenone to famish stereoselectively oxazolinyl oxiranes and formyl oxiranes. The stereoselection observed has been related to the geometry of the intermediate lithium azaenolates. Calculations have been carried out in order to evaluate the relative stability of the E and Z forms of the lithium azaenolates. The reaction of a lithium azaenolate with other ketones leading to oxazolinyl epoxides is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Boron azaenolates of chiral oxazolines: synthesis of optically active formyl oxiranes
  作者：Saverio Florio、Vito Capriati、Renzo Luisi、Alessandro Abbotto

  DOI：10.1016/s0040-4039(99)01480-x

  日期：1999.10

  Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1). (C) 1999 Elsevier Science Ltd. All rights reserved.
• A Stereospecific Synthesis of Oxazolinyloxiranes
  作者：Alessandro Abbotto、Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi、Marcel Pierrot、Antonio Salomone

  DOI：10.1021/jo0057607

  日期：2001.5.1

  Lithiooxiranes 3a and 3b, generated by deprotonation of oxiranes 2a and 2b with s-BuLi at - 100 degreesC in Et2O, were found to be chemically very stable. trans-Lithiooxirane 3a was also configurationally stable and reacted stereospecifically with electrophiles to give 4a-k. In contrast, cis-lithiooxirane 3b was found to be configurationally much less stable and reacted with electrophiles affording mixtures of diastereomers 4, 7, and 8, After only a very short reaction time, 3b too reacted with electrophiles highly stereospecifically. Deprotonation-deuteration and deprotonation-alkylation of chiral oxazolinyloxiranes 12a and 12b to give oxiranes 12c and 12d were also examined. Semiempirical and ab initio calculations were carried out in an effort to explain the observed stereochemistry.
• Synthesis via oxazolines IX. An asymmetric synthesis of 2-methoxy and 2-chloroalkanoic acids
  作者：A.I. Meyers、Gerald Knaus、Peter M. Kendall

  DOI：10.1016/s0040-4039(01)91946-x

  日期：1974.1