(1R,7aS)-1-ethenyl-3-oxotetrahydro-1H,3H-pyrrolo<1,2-c>oxazole | 146925-70-4

• 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: (1R,7aS)-1-ethenyl-3-oxotetrahydro-1H,3H-pyrrolo<1,2-c>oxazole
• 英文别名: (1R,7aS)-1-ethenyl-3-oxotetrahydro-1H,3H-pyrrolo[1,2-c]oxazole；(1R,7aS)-1-ethenyl-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 146925-70-4
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: MNGBMMWYHCOEPL-NKWVEPMBSA-N

物化性质

• 沸点：
  313.3±22.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 sodium tetrahydroborate 、 pyridine-SO3 complex 、 sodium hydride 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.17h， 生成 (1R,7aS)-1-ethenyl-3-oxotetrahydro-1H,3H-pyrrolo<1,2-c>oxazole
  参考文献：
  名称：

  Syn-SN2' pathway in the reaction of certain .gamma.-(mesyloxy) .alpha.,.beta.-enoates with RCu(CN)MgX.BF3 reagents. Importance of MgX and bulky R group upon the diastereoselectivity

  摘要：

  The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.

  DOI：

  10.1021/jo00057a038

文献信息

• Highly Stereoselective Intramolecular S_N2′ Cyclization Yielding Chiral ­Oxazolidin-2-ones: General Route to α-Hydroxy-β-amino Acids
  作者：Ki Hun Park、Woo Duck Seo、Marcus J. Curtis-Long、Jin Hyo Kim、Jong Keun Park、Ki Min Park

  DOI：10.1055/s-2005-872264

  日期：——

  Intramolecular nucleophilic attack onto allylsulfonates promoted by silica gel acting as an acid catalyst provides expedient stereoselective access to 4,5-difunctionalized oxazolidin-2-ones. Precursors were prepared efficiently from enantiopure α-amino acids and subsequent manipulation of the oxazolidin-2-ones yielded enantiopure α-hydroxy-β-amino acids.

  硅胶作为酸催化剂促进对烯丙基磺酸盐的分子内亲核攻击提供了对 4,5-双官能化 2-酮的立体选择性访问。前体是由对映纯的 α-氨基酸有效制备的，随后对恶唑烷-2-酮的操作产生了对映纯的 α-羟基-β-氨基酸。
• Pd-catalyzed ScN' reactions: Stereoselective formation of cyclic carbamates from tert-butyldimethylsilyl carbamates
  作者：Glen W. Spears、Koji Nakanishi、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(00)98065-1

  日期：1990.1

  Stereoselective formation of cyclic carbamates was achieved by the intramolecular trapping of a tert-butyldimethylsilyloxycarbonyl group with allylic esters upon activation with fluoride and cat. Pd(O). The reactive conformation is proposed to be D. The highly stereo;elective reaction of 2° allylic esters allowed a detailed reaction mechanism to be proposed which accounts for the observed selectivities

  环状氨基甲酸酯的立体选择性形成是通过在烯丙基酯的作用下用氟化物和猫活化而将叔丁基二甲基甲硅烷基氧基羰基分子内捕获而实现的。钯（O）。所述反应性构象建议成为d。2°烯丙基酯的高度立体选择性反应可以提出详细的反应机理，从而说明了所观察到的选择性。
• Ibuka Toshiro, Taga Tooru, Habashita Hiromu, Nakai Kazuo, Tamamura Hiroka+, J. Org. Chem, 58 (1993) N 5, S 1207-1214
  作者：Ibuka Toshiro, Taga Tooru, Habashita Hiromu, Nakai Kazuo, Tamamura Hiroka+

  DOI：——

  日期：——
• Syn-SN2' pathway in the reaction of certain .gamma.-(mesyloxy) .alpha.,.beta.-enoates with RCu(CN)MgX.BF3 reagents. Importance of MgX and bulky R group upon the diastereoselectivity
  作者：Toshiro Ibuka、Tooru Taga、Hiromu Habashita、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yukiyasu Chounan、Hisao Nemoto、Yoshinori Yamamoto

  DOI：10.1021/jo00057a038

  日期：1993.2

  The reactions of protected serine- and threonine-derived gamma-(mesyloxy) alpha,beta-unsaturated esters with various magnesio organocyanocopper Lewis acid complexes have been investigated. The formation of syn-S(N)2' products, in addition to the normally expected anti-S(N)2' products, is taken as an indication that the reaction proceeds by a mechanism involving coordination of the magnesiocuprate with the C(delta)-N:C(gamma)-O syn-gamma-(mesyloxy) alpha,beta-enoates.