methyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-4,5-dihydro-1H-4-imidazolecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-4,5-dihydro-1H-4-imidazolecarboxylate
• 英文别名: 4-(methoxycarbonyl)-5-phenyl-N-tosyl-2-imidazoline；methyl (4S,5R)-1-(4-methylphenyl)sulfonyl-5-phenyl-4,5-dihydroimidazole-4-carboxylate
• 化学式: C₁₈H₁₈N₂O₄S
• 分子量: 358.418
• InChiKey: XNEIKJUGWXHQSU-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-4,5-dihydro-1H-4-imidazolecarboxylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-4,5-dihydro-1H-4-imidazolecarboxylate
  参考文献：
  名称：

  金催化的N-磺酰基醛亚胺与异氰基乙酸甲酯的赤藓醇选择性醛醇缩合反应（I）

  摘要：

  在1mol％的AuCl（c -HexNC）存在下，N-甲苯磺酰基亚胺1与异氰基乙酸甲酯反应，得到具有高（超过89％）顺式选择性的4-甲氧基羰基-5-烷基-2-咪唑啉2。通过用三乙胺处理将顺式-咪唑啉羧酸酯异构化为反式异构体。该水解顺式-和反式- imidazolinecarboxylates给赤-和苏- α，β分别为二氨基酸。

  DOI：

  10.1016/0040-4039(96)00981-1

文献信息

• Palladium Pincer Complex-Catalyzed Condensation of Sulfonimines and Isocyanoacetate to Imidazoline Derivatives. Dependence of the Stereoselectivity on the Ligand Effects
  作者：Juhanes Aydin、K. Senthil Kumar、Lars Eriksson、Kálmán J. Szabó

  DOI：10.1002/adsc.200700242

  日期：2007.12.10

  studies revealed that the PCP complex-catalyzed reaction proceeds via an η1-coordinated palladium isocyanoacetate pincer intermediate. This intermediate could also be isolated and its structure was determined by X-ray diffraction. The X-ray structure of this reaction intermediate indicates a surprisingly strong carbon-metal bond between the palladium atom and the coordinated isocyanoacetate molecule

  使用各种PCP，SCS，SeCSe和NCN钳形配合物作为催化剂，进行亚胺与异氰基乙酸酯的钯催化缩合反应。使用仅1mol％的没有任何添加剂的夹钳络合物催化剂，反应在室温下快速进行（2小时）。缺电子的和相对笨重PCP复合物提供咪唑啉衍生物具有非常高的顺式非对映选择性。事实证明，所施加的PCP催化剂在所施加的反应条件下非常耐用，因为在完成催化过程后，它可以回收而不会分解。通过使用富电子的SeCSe型络合物，可以逆转缩合反应的立体选择性。简单的钯盐，例如乙酸钯，Pd（OAc）2催化差的立体选择性的反应。PCP络合物催化过程的立体选择性并不明显取决于亚磺胺成分的空间体积。机制研究揭示，PCP配合物催化反应的进行经由一个η 1个配位的钯异氰基钳形中间。也可以分离该中间体，并通过X射线衍射确定其结构。该反应中间体的X射线结构表明钯原子与配位的异氰基乙酸酯分子之间的碳-金属键出奇地强。我们的机理研究表明，
• Copper(I)-catalyzed diastereoselective formation of oxazolines and N-sulfonyl-2-imidazolines
  作者：David Benito-Garagorri、Vladica Bocokić、Karl Kirchner

  DOI：10.1016/j.tetlet.2006.10.040

  日期：2006.12

  A simple and short method for the reaction of methyl isocyanoacetate with aldehydes and N-sulfonylimines is presented. The reaction is catalyzed by copper(I) complexes and proceeds with excellent yields and high diastereoselectivities.

  提出了一种简单而又简短的方法，用于异氰基乙酸甲酯与醛和N-磺酰亚胺的反应。该反应由铜（I）配合物催化，并以优异的产率和高的非对映选择性进行。
• Ruthenium Complex-Catalyzed Reaction of Isocyanoacetate and <i>N</i>-Sulfonylimines:  Stereoselective Synthesis of <i>N</i>-Sulfonyl-2-Imidazolines
  作者：Ying-Rui Lin、Xiao-Ti Zhou、Li-Xin Dai、Jie Sun

  DOI：10.1021/jo961598p

  日期：1997.3.1

  Ruthenium(II)-catalyzed reaction of N-sulfonylimines with methyl isocyanoacetate proceeds efficiently under neutral, mild conditions to give trans-2-imidazolines stereoselectively in high yields. 2,3-Diamino acids can be easily acquired via the hydrolysis of the imidazolines in excellent yields. A possible mechanism for the ruthenium-catalyzed aldol reaction of the imines under neutral conditions is discussed.
• Organocatalytic asymmetric Mannich-type reaction of N-sulfonylimines with isocyanoacetate leading to optically active 2-imidazoline-4-carboxylates
  作者：Zhen-Wei Zhang、Gui Lu、Miao-Miao Chen、Ning Lin、Yong-Bo Li、Tamio Hayashi、Albert S.C. Chan

  DOI：10.1016/j.tetasy.2010.04.029

  日期：2010.7

  The first asymmetric Mannich-type reaction of methyl isocyanoacetate with N-sulfonylimines catalyzed by cinchona alkaloid derivatives yielded 2-imidazolines with high diastereoselectivities and good enantioselectivities (up to >99:1 dr and 70% ee). This reaction provided a convenient route to access various substituted 2-imidazoline-4-carboxylates and related alpha,beta-diamino acids in high enantiomeric purities. (C) 2010 Elsevier Ltd. All rights reserved.
• Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate
  作者：Juhanes Aydin、Andreas Rydén、Kálmán J. Szabó

  DOI：10.1016/j.tetasy.2008.07.027

  日期：2008.8

  The asymmetric condensation of isocyanoacetate and sulfonimines was studied. Chiral BINOL and biphenantrol-based palladium-pincer complexes proved to be efficient catalysts affording 2-imidazoline derivatives with up to 86% ee. The level of enantioselectivity was clearly dependent on the gamma-substituents of the BINOL ring. The best results were obtained by using biphenantrol-based pincer-complex catalysts. Some of the complexes induced the selective formation of the anti-diastereorner of the 2-imidazoline. The diastereo- and enantioselectivity showed an interesting solvent dependence as well. It was found that the application of diglyme as a solvent instead of THF leads to preferential formation of the anti product with a slight decrease of the enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.