(4S,5R)-1-[(E)-hex-2-enoyl]-3,4-dimethyl-5-phenylimidazolidin-2-one | 139962-44-0

• 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: (4S,5R)-1-[(E)-hex-2-enoyl]-3,4-dimethyl-5-phenylimidazolidin-2-one
• CAS: 139962-44-0
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: CCOSEKNMGLKADA-TWSPDMLNSA-N

物化性质

• 沸点：
  397.4±45.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-[(E)-hex-2-enoyl]-3,4-dimethyl-5-phenylimidazolidin-2-one 在 正丁基锂 、 氨 、 溴 、 甲基氯化镁 、 copper(ll) bromide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.67h， 生成 (4R,5S)-1,5-dimethyl-3-[(2E)-3-phenyl-2-propenoyl]-4-phenyl-2-imidazolidinone
  参考文献：
  名称：

  非对映选择性加布里埃尔-克罗姆韦尔反应合成对映体纯的反式氮丙啶-2-羧酸酯

  摘要：

  通过将氨共轭添加到α，β-不饱和手性酰亚胺中，然后用苄氧基锂处理，可以高产率和选择性地获得苄基氮丙啶-2-羧酸苄酯。氮丙啶环扩展成恶唑啉可以确定新形成的立体异构中心的绝对立体化学。

  DOI：

  10.1016/0957-4166(96)00071-7
• 作为产物：
  描述：

  盐酸右旋麻黄碱 在 2,3-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (4S,5R)-1-[(E)-hex-2-enoyl]-3,4-dimethyl-5-phenylimidazolidin-2-one
  参考文献：
  名称：

  Additions diastéréosélectives d'alkyl, alcényl, aryl et allyl cuprates à des imides chirales insaturées

  摘要：

  Some diastereoselective conjugate additions of cuprates to chiral unsaturated imides hearing an imidazolidinyl group (from ephedrine and urea) show an impressive stereoselectivity. The chiral (internal auxiliary dependent) group is easily broken and recycled. The steric course of these reactions seems quite general and its development promising in synthesis.

  DOI：

  10.1016/s0040-4020(01)88188-6

文献信息

• Synthesis of Enantiomerically Pure Aziridine-2-imides by Cyclization of Chiral 3‘-Benzyloxyamino Imide Enolates
  作者：Alessandro Bongini、Giuliana Cardillo、Luca Gentilucci、Claudia Tomasini

  DOI：10.1021/jo971254e

  日期：1997.12.1

  Aziridine-2-imides are prepared both in high yield and high diastereoselectivity from chiral 3'-benzyloxyamino imides 2, 3, and 8 by treatment with triethylamine in the presence of either TiCl4 or AlMe2Cl. 2 and 3 are easily obtained by a diastereoselective conjugate addition of O-benzylhydroxylamine promoted by Lewis acids to alpha,beta-unsaturated imides 1. The synthesis of 3'-(benzyloxyamino)propanoyl 8 is performed by addition to the acryloyl compound 6 of N-BOC O-benzylhydroxylamine followed by deprotection. The cyclization of 2 and 3 affords complete trans selectivity and yields up to 97% of the corresponding 3'-alkyl aziridines 4 and 5, while the cyclization of 8 affords a mixture of diasteroisomers 11, 12 in 86/14 ratio and a 95% yield. A mechanistic study has been made to rationalize the trans selectivity observed in the cyclization of 2 and 3. AM1 computations allow us to deduce that the reaction proceeds through cyclic titanium or aluminum enolate formation, and they reveal that enolates leading to trans aziridines are more stable than those leading to cis.
• Cardillo, Giuliana; Casolari, Sonia; Gentilucci, Luca, Angewandte Chemie, 1996, vol. 108, # 16, p. 1939 - 1941
  作者：Cardillo, Giuliana、Casolari, Sonia、Gentilucci, Luca、Tomasini, Claudia

  DOI：——

  日期：——