(4R,5S)-(-)-1,5-dimethyl-4-phenyl-3-(2-phenylethynyl)-2-imidazolidinone | 332183-35-4

• 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: (4R,5S)-(-)-1,5-dimethyl-4-phenyl-3-(2-phenylethynyl)-2-imidazolidinone
• 英文别名: (4R,5S)-1,5-dimethyl-4-phenyl-3-(phenylethynyl)imidazolidin-2-one；(4R,5S)-1,5-Dimethyl-4-phenyl-3-(phenylethynyl)imidazolidin-2-one；(4R,5S)-1,5-dimethyl-4-phenyl-3-(2-phenylethynyl)imidazolidin-2-one
• CAS: 332183-35-4
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: QNACKCYLRYOQIZ-YJBOKZPZSA-N

物化性质

• 熔点：
  187-188 °C
• 沸点：
  421.7±48.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R,5S)-(-)-1,5-dimethyl-4-phenyl-3-(2-phenylethynyl)-2-imidazolidinone 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 以77%的产率得到1-((4S,5R)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl)-2-phenylethane-1,2-dione
  参考文献：
  名称：

  Synthesis of α-Keto-Imides via Oxidation of Ynamides

  摘要：

  A de novo preparation of alpha-keto-imides via ynamide oxidation is described. With a number of alkyne oxidation conditions screened, a highly efficient RuO2-NaIO4 mediated oxidation and a DMDO oxidation have been identified to tolerate a wide range of ynamide types. In addition to accessing a wide variety of a-keto-imides, the RuO2-NaIO4 protocol provides a novel entry to the vicinal tricarboryl motif via oxidation of push-pull ynamides, and imido acylsilanes from silyl-substituted ynamides. Chemoselective oxidation of ynamides containing olefins can be achieved by using DMDO, while the RuO2-NaIO4 protocol is not effective. These studies provide further support for the synthetic utility of ynamides.

  DOI：

  10.1021/jo8015067
• 作为产物：
  描述：

  (4S,5R)-1-((Z)-2-Bromo-2-phenyl-vinyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以40%的产率得到(4R,5S)-(-)-1,5-dimethyl-4-phenyl-3-(2-phenylethynyl)-2-imidazolidinone
  参考文献：
  名称：

  新型炔酰胺和烯丙酰胺的有效制剂

  摘要：

  在此描述了一系列新型的酰胺和烯丙酰胺的实用合成。尽管炔丙基酰胺的碱诱导的异构化方案导致一系列手性和非手性烯丙酰胺，但是通过溴化由酰胺制备炔基酰胺，然后进行碱诱导的Z-溴烯酰胺的消除。与炔胺和烯丙胺相比，这些炔酰胺和烯丙酰胺具有改进的热稳定性。它们可以轻松分离，纯化和处理，因此在合成上应比传统的ynamines和allenamines更有用。

  DOI：

  10.1016/s0040-4020(00)01014-0

文献信息

• Copper-Mediated N-Alkynylation of Carbamates, Ureas, and Sulfonamides. A General Method for the Synthesis of Ynamides
  作者：Joshua R. Dunetz、Rick L. Danheiser

  DOI：10.1021/ol035647d

  日期：2003.10.1

  [reaction: see text] A general amination strategy for the N-alkynylation of carbamates, sulfonamides, and chiral oxazolidinones and imidazolidinones is described. A variety of substituted ynamides are available by deprotonation of amides with KHMDS followed by reaction with CuI and an alkynyl bromide.

  [反应：见正文] 描述了氨基甲酸酯、磺酰胺、手性恶唑烷酮和咪唑烷酮的 N-炔基化的一般胺化策略。通过用 KHMDS 对酰胺进行去质子化，然后与 CuI 和炔基溴反应，可以获得各种取代的炔酰胺。
• Copper-Catalyzed Alkynylation of Amides with Potassium Alkynyltrifluoroborates: A Room-Temperature, Base-Free Synthesis of Ynamides
  作者：Kévin Jouvin、François Couty、Gwilherm Evano

  DOI：10.1021/ol101322k

  日期：2010.7.16

  An efficient copper-mediated method for the coupling of potassium alkynyltrifluoroborates with nitrogen nucleophiles is reported. This reaction provides the first base-free and room-temperature synthesis of ynamides and allows for an easy preparation of these useful building blocks.

  报道了一种有效的铜介导的方法，用于将炔基三氟硼酸钾与氮亲核试剂偶联。该反应提供了首个无碱和室温下合成的酰胺，可轻松制备这些有用的结构单元。
• Highly regio- and stereocontrolled synthesis of β-substituted α-tributylstannyl enamides
  作者：David Buissonneaud、Jean-Christophe Cintrat

  DOI：10.1016/j.tetlet.2006.02.141

  日期：2006.5

  The regio- and stereocontrolled synthesis of β-substituted α-stannyl enamides is reported starting from internal ynamides. The synthesis of new ynamides as well as bis-ynamides is also described. Finally first examples of successful cross-coupling to afford α/β-disubstituted enamides are also reported.

  据报道，β-取代的α-锡烷基烯酰胺的区域和立体控制合成是从内部的酰胺开始的。还描述了新的乙酰胺和双乙酰胺的合成。最后，还报道了成功交叉偶联以提供α/β-二取代的酰胺的第一个例子。
• SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE
  作者：Kohnen, Amanda L.、Dunetz, Joshua R.、Danheiser, Rick L.、Denmark, Scott E.、Liu, Xiaorong

  DOI：10.15227/orgsyn.084.0088

  日期：——
• Copper Sulfate-Pentahydrate-1,10-Phenanthroline Catalyzed Amidations of Alkynyl Bromides. Synthesis of Heteroaromatic Amine Substituted Ynamides
  作者：Yanshi Zhang、Richard P. Hsung、Michael R. Tracey、Kimberly C. M. Kurtz、Eymi L. Vera

  DOI：10.1021/ol049827e

  日期：2004.4.1

  A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO(4)(.)5H(2)O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.