5-[1-Cyclohexyl-meth-(E)-ylidene]-imidazolidine-2,4-dione | 122344-95-0

• 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: 5-[1-Cyclohexyl-meth-(E)-ylidene]-imidazolidine-2,4-dione
• 英文别名: 5-(Cyclohexylmethylidene)imidazolidine-2,4-dione
• CAS: 122344-95-0
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: CONDDCCDTHKSBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[1-Cyclohexyl-meth-(E)-ylidene]-imidazolidine-2,4-dione 在 sodium hydroxide 作用下， 以 水 为溶剂， 以50 %的产率得到3-cyclohexyl-2-oxo-propionic acid
  参考文献：
  名称：

  使用铱基氢转移催化剂进行 α-酮酸的不对称还原胺化：获得未受保护的非天然 α-氨基酸

  摘要：

  描述了由带有手性N- (2-吡啶甲基)磺酰胺基配体的 Cp*Ir 配合物催化的 α-酮酸的直接不对称还原胺化。组合使用光学活性2-苯甘氨醇作为胺化剂对于使用甲酸的化学选择性和立体选择性转移氢化是有效的。随后用原高碘酸消除羟乙基部分可以以令人满意的分离产率（20个实例）提供各种未保护的α-氨基酸，并具有优异的光学纯度（高达> 99% ee）。

  DOI：

  10.1021/acs.orglett.3c04378
• 作为产物：
  描述：

  5-风化煤磷酸二乙酯 、 环己烷基甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以91%的产率得到5-[1-Cyclohexyl-meth-(E)-ylidene]-imidazolidine-2,4-dione
  参考文献：
  名称：

  Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives

  摘要：

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.

  DOI：

  10.1021/jo00024a036

文献信息

• Diethyl 2,4-dioxoimidazolidine-5-phosphonates: Horner-Wadsworth-Emmons reagents for the mild and efficient preparation of C-5 unsaturated hydantoin derivatives
  作者：Nicholas A. Meanwell、Herbert R. Roth、Edward C. R. Smith、Donald L. Wedding、J. J. Kim Wright

  DOI：10.1021/jo00024a036

  日期：1991.11

  The phosphonates 19 and 20 were prepared from hydantoin and 1-methylhydantoin, respectively, by way of bromination at C-5 and a subsequent Michaelis-Arbuzov reaction with triethyl phosphite. The Horner-Wadsworth-Emmons-type reagents 19 and 20 were found to react readily with aromatic and aliphatic aldehydes, in the presence of a base, to produce C-5 unsaturated hydantoin derivatives 22 and 26, generally in high yield. The products 22 and 26 were frequently isolated as mixtures of E and Z isomers depending upon the identity of the aldehyde and phosphonate. The isomeric configuration of the products was determined from an analysis of NMR spectral data. Long-range C-13-H-1 coupling constants between the C-4 carbonyl of the hydantoin ring and the olefinic proton were found to be diagnostic of isomer geometry. Conditions were also developed that allowed coupling of 19 and 20 with cyclic and acyclic ketones and alpha-dicarbonyl compounds to afford the corresponding olefinic products. C-5 unsaturated hydantoin derivatives are of synthetic utility as precursors to alpha-amino acid derivatives, pyruvates, and the imidazo[4,5-b]quinolin-2-one heterocyclic ring system, a class of potent inhibitors of low Km cAMP phosphodiesterase and the chromophore present in the siderophore azotobactin.
• Asymmetric Reductive Amination of α-Keto Acids Using Ir-Based Hydrogen Transfer Catalysts: An Access to Unprotected Unnatural α-Amino Acids
  作者：Takaaki Yajima、Akito Katayama、Tsubasa Ito、Takuma Kawada、Kenya Yabushita、Toshihisa Yasuda、Takeshi Ohta、Takeaki Katayama、Noriyuki Utsumi、Yoshihito Kayaki、Shigeki Kuwata

  DOI：10.1021/acs.orglett.3c04378

  日期：2024.2.23

  A direct asymmetric reductive amination of α-keto acids catalyzed by Cp*Ir complexes bearing a chiral N-(2-picolyl)sulfonamidato ligand is described. The combined use of optically active 2-phenyglycinol as an aminating agent is effective for the chemo- and stereoselective transfer hydrogenation using formic acid. The subsequent elimination of the hydroxyethyl moiety by orthoperiodic acid can afford

  描述了由带有手性N- (2-吡啶甲基)磺酰胺基配体的 Cp*Ir 配合物催化的 α-酮酸的直接不对称还原胺化。组合使用光学活性2-苯甘氨醇作为胺化剂对于使用甲酸的化学选择性和立体选择性转移氢化是有效的。随后用原高碘酸消除羟乙基部分可以以令人满意的分离产率（20个实例）提供各种未保护的α-氨基酸，并具有优异的光学纯度（高达> 99% ee）。