acrylic 2,2-dimethyl-5(R)-phenyl-1,3-oxazolidinide | 139255-93-9

• 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: acrylic 2,2-dimethyl-5(R)-phenyl-1,3-oxazolidinide
• 英文别名: (R)-3-acryloyl-2,2-dimethyl-4-phenyloxazolidine；acrylic 2,2-dimethyl-5(S)-phenyl-1,3-oxazolidinide；1-[(4R)-2,2-dimethyl-4-phenyl-1,3-oxazolidin-3-yl]prop-2-en-1-one
• CAS: 139255-93-9
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: YLVMZXJBFMBOAI-LBPRGKRZSA-N

物化性质

• 沸点：
  391.4±41.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  acrylic 2,2-dimethyl-5(R)-phenyl-1,3-oxazolidinide 在 三乙基硼氢化锂 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-<(1R)-2-hydroxy-1-phenylethyl>-(5S)-3-phenyl-2-isoxazoline-5-carboxamide
  参考文献：
  名称：

  22，-二甲基-4-苯基恶唑啉和2,2-二甲基-4,5-二苯基咪唑烷作为新的手性助剂。在不对称丁腈环氧化物加成中的应用

  摘要：

  显示两种新手性助剂（R）-2,2-二甲基-4-苯基恶唑烷和（S，S）-2,2-二甲基-4,5-二苯基咪唑烷的丙烯酰胺衍生物的腈氧化物的不对称偶极环加成反应令人满意的高非对映选择性（高达91％）。

  DOI：

  10.1016/s0957-4166(00)80018-x
• 作为产物：
  描述：

  D-苯甘氨醇 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(R)-phenyl-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）
• Racemic and asymmetric cobalt-catalysed reductive aldol couplings of α,β-unsaturated amides with ketones
  作者：Ralph J.R. Lumby、Pekka M. Joensuu、Hon Wai Lam

  DOI：10.1016/j.tet.2008.06.022

  日期：2008.8

  In the presence of diethylzinc as a stoichiometric reductant, substoichiometric quantities of an appropriate cobalt source catalyse diastereoselective reductive aldol coupling reactions of α,β-unsaturated amides with ketones. The use of a readily available oxazolidine as a chiral auxiliary imparts high levels of asymmetric induction in these reactions.

  在二乙基锌作为化学计量的还原剂的存在下，亚化学计量的适当的钴源催化α，β-不饱和酰胺与酮的非对映选择性还原羟醛偶联反应。在这些反应中，容易获得的恶唑烷用作手性助剂会引起高水平的不对称诱导。
• Free radical macrocyclizations from steroid-derived precursors
  作者：Daniel M. Scott、Andrew T. McPhail、Ned A. Porter

  DOI：10.1021/jo00057a034

  日期：1993.2

  Stereoselective free radical addition reactions were studied using steroid-derived templates in an attempt to control product dispersity. Templates were prepared from bifunctional steroids appropriately substituted with initiating and terminating functionality. Free radical initiation in the presence of a polymerizable olefin resulted in the formation of macrocycles that had incorporated monomer. The yield of macrocycle formed was as high as 51 % for templates derived from lithocholic acid whereas templates derived from androstanolone failed to give significant amounts of macrocycles. The effects of variation of initiating and terminating functionality, steroid, and olefin on macrocycle size and yield were examined.
• 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.