(4S,5S)-4,5-dimethoxy-1-[(1S,2R)-2-exomethoxyapocamphanecarbonyl]-2-imidazolidinone | 374590-42-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S,5S)-4,5-dimethoxy-1-[(1S,2R)-2-exomethoxyapocamphanecarbonyl]-2-imidazolidinone
• 英文别名: (4S,5S)-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinone；(4S,5S)-4,5-dimethoxy-1-[(1S,2R,4R)-2-methoxy-7,7-dimethylbicyclo[2.2.1]heptane-1-carbonyl]imidazolidin-2-one
• CAS: 374590-42-8
• 化学式: C₁₆H₂₆N₂O₅
• 分子量: 326.393
• InChiKey: NADFZXUFKLLHOC-ZOUHWKOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4,5-dimethoxy-1-[(1S,2R)-2-exomethoxyapocamphanecarbonyl]-2-imidazolidinone 在 正丁基锂 、 三氟化硼乙醚 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  1,2-二胺的多功能手性合成子：（4 S，5 S）-和（4 R，5 R）-4,5-二甲氧基-2-咪唑啉酮

  摘要：

  （4 S，5 S）-和（4 R，5 R）-1-酰基-4,5-二甲氧基-2-咪唑啉酮衍生物可从简单的1,3-二氢-2-咪唑啉酮杂环容易获得新型手性合成子的良好候选者，可用于制备旋光性苏二胺，如2 S，3 R-和3 S，4 S-二氨基羧酸。

  DOI：

  10.1016/s0040-4039(01)01279-5
• 作为产物：
  描述：

  (4R,5R)-4,5-dimethoxy-1-(2-mesitylenesulfonyl)-2-imidazolidinone 在 sodium hydride 、 sodium cyanoborohydride 、 苯甲醚 作用下， 以 四氢呋喃 、 乙酸乙酯 、 mineral oil 为溶剂， 反应 2.75h， 生成 (4S,5S)-4,5-dimethoxy-1-[(1S,2R)-2-exomethoxyapocamphanecarbonyl]-2-imidazolidinone
  参考文献：
  名称：

  Highly Efficient Preparation of Both Enantiomers of Versatile Chiral Synthon for 1,2-Diamines via the Fe(III)-Catalyzed Oxidation of 2-Imidazolone

  摘要：

  A new method was established for the preparation of both of the enantiomers of trans-4,5-dimethoxy-2-imidazolidinone (DMIm) via the Fe(III)-catalyzed oxidation of 2-imidazolone by H2O2-urea, which allowed the subsequent achievement of optical resolution via the introduction of a MAC moiety. and a 2-mesitylenesulfonyl group at the two nitrogen positions of DMIm, which then were easily removed. The two enantiomers are useful as versatile chiral synthons for 1,2-diamines.

  DOI：

  10.3987/com-13-s(s)104

文献信息

• Enantioselective synthesis of (1S,2S)-1,2-di-tert-butyl and (1R,2R)-1,2-di-(1-adamantyl)ethylenediamines
  作者：Alaa A.-M. Abdel-Aziz、Serry A.A. El Bialy、Fatma E. Goda、Takehisa Kunieda

  DOI：10.1016/j.tetlet.2004.08.164

  日期：2004.10

  An enantioselective synthesis of sterically congested 1,2-di-tert-butyl and 1,2-di-(1-adamantyl)ethylenediamines has been developed. Thus, diastereomerically pure trans-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinones 6 and 7 were successfully prepared by optical resolution of (+/-)-trans-4,5-dimethoxy-2-imidazolidinone using apocamphanecarbonyl chloride (MAC-Cl) followed by stereospecific and stepwise substitution of the dimethoxyl groups using tert-butyl or 1-adamantyl cuprates to provide (4S,5S)-4,5-di-tert-butyl and (4R,5R)-4,5-di-(1-adamantyl)-2-imidazolidinones 12 and 15, respectively. Furthermore, N-acetyl 4,5-di-tert-butyl and 4,5-di-(1-adamantyl)-2-imidazolidinones 16a,b were enantioselectively deacetylated using a catalytic oxazaborolidine system to provide enantiopure 1-p-tolylsulfonyl-4,5-di-tert-butyl-2-imidazolidinones 12 and 19 and 1-p-tolylsulfonyl-4,5-di-(1-adamantyl)-2-imidazolidinones 18 and 20, respectively. Finally, N-p-tolylsulfonyl-2-imidazolidinones 12 and 15 were treated with 30equiv of Ba(OH)(2.)8H(2)O to achieve ring cleavage and to provide (1S,2S)-1,2-di-tert-butylethylenediamine 3 and (1R,2R)-1,2-di(1-adamantyl)ethylenediamine 4. (C) 2004 Elsevier Ltd. All rights reserved.