rac-3-acryloyl-2,2-pentamethylene-4-phenyloxazolidine | 144899-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: rac-3-acryloyl-2,2-pentamethylene-4-phenyloxazolidine
• 英文别名: 1-(3-Phenyl-1-oxa-4-azaspiro[4.5]decan-4-yl)prop-2-en-1-one
• CAS: 144899-49-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: OPOGTYYGMRDUGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-3-acryloyl-2,2-pentamethylene-4-phenyloxazolidine 、 benzohydroximoyl chloride 在 三乙胺 作用下， 生成 (4RS)-2,2-pentamethylene-4-phenyl-3-<(5RS)-3-phenyl-2-isoxazolidine-5-carbonyl>oxazolidine 、 (4RS)-2,2-pentamethylene-4-phenyl-3-<(5SR)-3-phenyl-2-isoxazoline-5-carbonyl>oxazolidine
  参考文献：
  名称：

  Highly lk-selective asymmetric nitrile oxide cycloadditions to a C2-symmetric 1,3-diacryloyl-2,2-dimethylimidazolidine and 4-chiral 3-acryloyl-2,2-dialkyloxazolidines

  摘要：

  1,3-Dipolar cycloadditions of benzonitrile oxide to the acrylamides derived from a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines show high lk-diastereoselectivities. Easy separation of the major lk-isomers from the minor ul-diastereomers is followed by reductive removal of the chiral auxiliaries to produce optically pure 2-isoxazoline-5-methanols. Absolute diastereoselectivities were recorded in the nitrile oxide cycloadditions of 3-acryloyl-2,2-dialkyl-4-(diphenylmethyl)oxazolidines at 0-degrees-C.

  DOI：

  10.1016/s0040-4020(01)89440-0
• 作为产物：
  描述：

  2,2-pentamethylene-4-phenyloxazolidine 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到rac-3-acryloyl-2,2-pentamethylene-4-phenyloxazolidine
  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

• 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.
• Highly lk-selective asymmetric nitrile oxide cycloadditions to a C2-symmetric 1,3-diacryloyl-2,2-dimethylimidazolidine and 4-chiral 3-acryloyl-2,2-dialkyloxazolidines
  作者：Shuji Kanemasa、Kenjiro Onimura

  DOI：10.1016/s0040-4020(01)89440-0

  日期：——

  1,3-Dipolar cycloadditions of benzonitrile oxide to the acrylamides derived from a C2-symmetric 2,2-dimethylimidazolidine and 4-chiral 2,2-dialkyloxazolidines show high lk-diastereoselectivities. Easy separation of the major lk-isomers from the minor ul-diastereomers is followed by reductive removal of the chiral auxiliaries to produce optically pure 2-isoxazoline-5-methanols. Absolute diastereoselectivities were recorded in the nitrile oxide cycloadditions of 3-acryloyl-2,2-dialkyl-4-(diphenylmethyl)oxazolidines at 0-degrees-C.