L-异亮氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1) | 29583-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: L-异亮氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1)
• 英文名称: (S)-5-((S)-sec-butyl)-3-phenyl-2-thioxoimidazolidin-4-one
• 英文别名: (5S)-5-[(2S)-butan-2-yl]-3-phenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 29583-07-1
• 化学式: C₁₃H₁₆N₂OS
• 分子量: 248.349
• InChiKey: NMRFWXLNHGJLIU-ONGXEEELSA-N

物化性质

• 沸点：
  337.8±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-异亮氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1) 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以66%的产率得到(S)-4-((S)-sec-butyl)-1-phenylimidazolidin-2-thione
  参考文献：
  名称：

  Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary

  摘要：

  Titanium mediated asymmetric Mannich reactions using imidazolidin-2-thione as a chiral auxiliary proceeded in good yields and with high diastereoselectivity to afford the anti-products in the presence of PPh3 additive. A non-chelated transition state with the PPh3-bound titanium enolate was proposed to explain the stereochemistry of the product. Alcoholysis of the adducts with methanol cleaved the imidazolidin-2-thione auxiliary to give the methyl esters in good yields and with excellent ee values. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.008
• 作为产物：
  描述：

  L-异亮氨酸 、 硫代异氰酸苯酯 在 三乙胺 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以95%的产率得到L-异亮氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1)
  参考文献：
  名称：

  Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary

  摘要：

  Titanium mediated asymmetric Mannich reactions using imidazolidin-2-thione as a chiral auxiliary proceeded in good yields and with high diastereoselectivity to afford the anti-products in the presence of PPh3 additive. A non-chelated transition state with the PPh3-bound titanium enolate was proposed to explain the stereochemistry of the product. Alcoholysis of the adducts with methanol cleaved the imidazolidin-2-thione auxiliary to give the methyl esters in good yields and with excellent ee values. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.008

文献信息

• Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary
  作者：Liang Zhu、Cuifen Lu、Zuxing Chen、Guichun Yang、Yan Li、Junqi Nie

  DOI：10.1016/j.tetasy.2014.11.008

  日期：2015.1

  Titanium mediated asymmetric Mannich reactions using imidazolidin-2-thione as a chiral auxiliary proceeded in good yields and with high diastereoselectivity to afford the anti-products in the presence of PPh3 additive. A non-chelated transition state with the PPh3-bound titanium enolate was proposed to explain the stereochemistry of the product. Alcoholysis of the adducts with methanol cleaved the imidazolidin-2-thione auxiliary to give the methyl esters in good yields and with excellent ee values. (C) 2014 Elsevier Ltd. All rights reserved.