acrylic 2,2-dimethyl-5(S)-isopropyl-1,3-oxazolidinide | 136570-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: acrylic 2,2-dimethyl-5(S)-isopropyl-1,3-oxazolidinide
• 英文别名: (S)-3-acryloyl-4-isopropyl-2,2-dimethyloxazolidine；1-[(4S)-2,2-dimethyl-4-propan-2-yl-1,3-oxazolidin-3-yl]prop-2-en-1-one
• CAS: 136570-12-2
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: BMSUWDPOSOISDJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 、 acrylic 2,2-dimethyl-5(S)-isopropyl-1,3-oxazolidinide 以 二氯甲烷 为溶剂， 生成 3-Cyclohexyl-1-((S)-4-isopropyl-2,2-dimethyl-oxazolidin-3-yl)-2-(pyridin-2-ylsulfanyl)-propan-1-one
  参考文献：
  名称：

  自由基加成立体选择性的起源：烯烃和带有恶唑烷和噻唑烷酰胺基团的自由基的反应

  摘要：

  报道了四种经过立体选择性自由基加成反应的烯烃的单晶 X 射线分析。这些烯烃的自由基加成的面部选择性是根据它们的固态构象来理解的。具有将基团置于空间位置的构象的烯烃在空间上保护一个面免于加成，以非对映面选择性进行自由基加成。烯烃的结构通过基团相对于进行加成的烯烃中心的极坐标进行分析

  DOI：

  10.1021/ja00046a010
• 作为产物：
  描述：

  L-缬氨醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.67h， 生成 acrylic 2,2-dimethyl-5(S)-isopropyl-1,3-oxazolidinide
  参考文献：
  名称：

  自由基加成立体选择性的起源：烯烃和带有恶唑烷和噻唑烷酰胺基团的自由基的反应

  摘要：

  报道了四种经过立体选择性自由基加成反应的烯烃的单晶 X 射线分析。这些烯烃的自由基加成的面部选择性是根据它们的固态构象来理解的。具有将基团置于空间位置的构象的烯烃在空间上保护一个面免于加成，以非对映面选择性进行自由基加成。烯烃的结构通过基团相对于进行加成的烯烃中心的极坐标进行分析

  DOI：

  10.1021/ja00046a010

文献信息

• Chiral auxiliary control of tacticity in free radical polymerization
  作者：Ned A. Porter、Timothy R. Allen、Robert A. Breyer

  DOI：10.1021/ja00046a011

  日期：1992.9

  Chiral oxazolidine acrylamides undergo stereocontrolled free radical polymerization. Remarkably high degrees of tacticity have been demonstrated in the polymerization of acrylamides with these chiral auxiliaries that are derived from valine, phenylglycine, and tert-leucine. The polyacrylamides formed in these polymerizations can be converted to poly(acrylic acid), P(AA), and poly(methyl acrylate),

  手性恶唑烷丙烯酰胺进行立体控制的自由基聚合。在丙烯酰胺与这些衍生自缬氨酸、苯基甘氨酸和叔亮氨酸的手性助剂的聚合中已经证明了显着的高规整度。在这些聚合中形成的聚丙烯酰胺可以通过水解和酯化转化为聚（丙烯酸）P（AA）和聚（丙烯酸甲酯）P（MA）
• 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.
• 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
• 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.
• Origins of stereoselectivity in radical additions: reactions of alkenes and radicals bearing oxazolidine and thiazolidine amide groups
  作者：Ned A. Porter、Ian J. Rosenstein、Robert A. Breyer、John D. Bruhnke、Wen Xue Wu、Andrew T. McPhail

  DOI：10.1021/ja00046a010

  日期：1992.9

  analysis of four alkenes that undergo stereoselective radical addition reactions are reported. The facial selectivity of radical additions to these alkenes is understood based upon their solid-state conformations. Alkenes which have a conformation placing a group at a position in space sterically protecting one the faces from addition undergo radical addition with diastereofacial selectivity. The structures

  报道了四种经过立体选择性自由基加成反应的烯烃的单晶 X 射线分析。这些烯烃的自由基加成的面部选择性是根据它们的固态构象来理解的。具有将基团置于空间位置的构象的烯烃在空间上保护一个面免于加成，以非对映面选择性进行自由基加成。烯烃的结构通过基团相对于进行加成的烯烃中心的极坐标进行分析