N-ethyl-2-oxo-2-phenyl-N-propan-2-ylacetamide | 171414-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-ethyl-2-oxo-2-phenyl-N-propan-2-ylacetamide
• CAS: 171414-28-1；178237-77-9；178237-78-0
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: TWLQZJLECOCHKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-ethyl-2-oxo-2-phenyl-N-propan-2-ylacetamide 在 (R,R)-(-)-trans-(2,3-bis-hydroxydiphenylmethyl)-1,4-dioxaspiro<5.4>decane 、 alkyl sulphate 作用下， 以 水 为溶剂， 反应 5.0h， 以72%的产率得到1-Ethyl-3-hydroxy-4,4-dimethyl-3-phenyl-azetidin-2-one
  参考文献：
  名称：

  主客体分子和晶体结构的设计

  摘要：

  摘要 当光学活性主体化合物与固态非手性客体化合物混合时，通过分子运动形成主客体包合物，非手性分子在包合物中以手性形式排列。

  DOI：

  10.1016/0022-2860(95)09090-8
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 、 N-乙基异丙基胺 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以32%的产率得到N-ethyl-2-oxo-2-phenyl-N-propan-2-ylacetamide
  参考文献：
  名称：

  Chiral Arrangement of N-Ethyl-N-isopropylphenylglyoxylamide Molecule in Its Own Crystal and in an Inclusion Crystal with a Host Compound and Their Photoreactions in the Solid State That Give Optically Active β-Lactam Derivatives. X-ray Analytical and CD Spectral Studies

  摘要：

  N-Ethyl-N-isopropylphenylglyoxylamide (3c) forms chiral crystal in which its achiral molecules are arranged in a chiral form, and the chirality in the crystal was identified by measurement of the CD spectrum in Nujol mull. Generation of the chirality occurs by twisting of the CO-CO bond of 3c in the crystal. Photoirradiation of the chiral crystal of 3c in the solid state gave optically active beta-lactam derivative (4c) of 80% ee. By X-ray analysis, absolute configurations of the chiral crystal and 4c were elucidated. The achiral molecules of 3c are also arranged in chiral forms in inclusion complexes with chiral hosts such as (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.4]nonane (5a), (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[5.4]decane (5b), and their (S,S)-(+)-enantiomers, 6a and 6b, respectively. The crystal structure of a 1:1 inclusion complex of 3c with 5b (7b) was analyzed. Photoirradiation of 7b in the solid state gave (R)-(+)-4c of 85% ee. Photochemical conversions of some other derivatives of 3c to the corresponding beta-lactams were also studied. Interestingly, however, irradiation of the 1:1 inclusion complex of N,N-dimethylglyoxylamide (3a) with 5a, which had been prepared by mixing both components in the absence of solvent, gave (R)-(+)-beta-lactam (9a) of 45% ee, although the 1:1 complex that had been prepared by recrystallization of the components from toluene gave (S)-(-)-9a of 100% ee. Mixing of powdered chiral (-)-3c crystal with a 2:1 inclusion complex of 5b and MeOH gave a new 1:1 complex of 5b and chiral (+)-3c, The inversion of the chirality of 3c in the solid state was studied by continuous measurements of CD spectra in Nujol mulls.

  DOI：

  10.1021/jo971584z

文献信息

• Achiral Molecules Move and Order Themselves in a Chiral Form in Host-Guest Inclusion Crystals
  作者：Fumio Toda、Hisakazu Miyamoto

  DOI：10.1246/cl.1995.809

  日期：1995.9

  When optically active host compound was mixed with achiral guest compound in the solid state, host-guest inclusion crystals were formed by molecular movement and the achiral molecules became arranged in a chiral form in the inclusion crystals. Mixing of powdered (+)-host crystals with powdered (−)-guest crystals which are formed by a chiral arrangement of achiral guest molecules gave inclusion crystals of the (+)-host and the (+)-guest molecules newly produced through an inversion of the (−)-guest molecules during the complexation in the solid state.

  当光学活性主化合物与非手性客体化合物在固态下混合时，通过分子运动形成了主-客体包晶，非手性分子在包晶中呈手性排列。将粉末状(+)-主晶与粉末状(-)-客晶混合，后者是由非手性客体分子的手性排列形成的，在固态络合过程中，通过(-)-客体分子的反转，产生了新的(+)-主晶和(+)-客体分子的包合物晶体。
• Miyamoto, Hisakazu; Kikuchi, Siro; Oki, Yasuo, Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1996, vol. 276-277, p. 73 - 78
  作者：Miyamoto, Hisakazu、Kikuchi, Siro、Oki, Yasuo、Inoue, Mitsuhiro、Kanemoto, Kazuyuki、Toda, Fumio

  DOI：——

  日期：——
• [DE] HAARBEHANDLUNGSVERFAHREN MIT VERBESSERTER PFLEGELEISTUNG SOWIE VORRICHTUNG UND MITTEL ZUR DURCHFÜHRUNG DES VERFAHRENS<br/>[EN] HAIR TREATMENT METHOD THAT PROVIDES IMPROVED HAIR CARE AND AGENT FOR CARRYING OUT SAID METHOD<br/>[FR] PROCEDE DE TRAITEMENT DES CHEVEUX CARACTERISE PAR UNE EFFICACITE DE SOIN AMELIOREE ET PRODUIT POUR METTRE EN OEUVRE CE PROCEDE
  申请人：HENKEL KGAA

  公开号：WO2007048472A1

  公开（公告）日：2007-05-03

  [EN] The invention relates to a method for treating keratin fibres, in particular human hair. According to said method, a hair treatment agent is applied to the hair and the hair thus treated is subsequently irradiated with UV radiation in the wavelength range of 200 to 600 nm for 1 to 60 minutes. Said method improves the hair care characteristics of the treated hair.
  [FR] L'invention concerne des procédés de traitement de fibres kératiniques, en particulier de traitement des cheveux, ces procédés consistant à appliquer sur les cheveux un produit de traitement des cheveux, puis à exposer les cheveux traités après application du produit à un rayonnement ultraviolet dans une gamme de longueurs d'onde comprise entre 200 et 600 nm pendant 1 à 60 minutes. Ces procédés permettent d'améliorer les propriétés de soin des cheveux ainsi traités.
  [DE] Verfahren zur Behandlung keratinischer Fasern, insbesondere menschlicher Haare, bei denen ein Haarbehandlungsmittel auf die Haare aufgebracht und das behandelte Haar im Anschluß an das Aufbringen des Mittels 1 bis 60 Minuten lang mit UV-Strahlung im Wellenlängenbereich 200 bis 600 nm bestrahlt wird, führen zu verbesserten Pflegeeigenschaften der so behandelten Haare.
• Chiral Arrangement of <i>N</i>-Ethyl-<i>N</i>-isopropylphenylglyoxylamide Molecule in Its Own Crystal and in an Inclusion Crystal with a Host Compound and Their Photoreactions in the Solid State That Give Optically Active β-Lactam Derivatives. X-ray Analytical and CD Spectral Studies
  作者：Fumio Toda、Hisakazu Miyamoto、Hideko Koshima、Zofia Urbanczyk-Lipkowska

  DOI：10.1021/jo971584z

  日期：1997.12.1

  N-Ethyl-N-isopropylphenylglyoxylamide (3c) forms chiral crystal in which its achiral molecules are arranged in a chiral form, and the chirality in the crystal was identified by measurement of the CD spectrum in Nujol mull. Generation of the chirality occurs by twisting of the CO-CO bond of 3c in the crystal. Photoirradiation of the chiral crystal of 3c in the solid state gave optically active beta-lactam derivative (4c) of 80% ee. By X-ray analysis, absolute configurations of the chiral crystal and 4c were elucidated. The achiral molecules of 3c are also arranged in chiral forms in inclusion complexes with chiral hosts such as (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.4]nonane (5a), (R,R)-(-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[5.4]decane (5b), and their (S,S)-(+)-enantiomers, 6a and 6b, respectively. The crystal structure of a 1:1 inclusion complex of 3c with 5b (7b) was analyzed. Photoirradiation of 7b in the solid state gave (R)-(+)-4c of 85% ee. Photochemical conversions of some other derivatives of 3c to the corresponding beta-lactams were also studied. Interestingly, however, irradiation of the 1:1 inclusion complex of N,N-dimethylglyoxylamide (3a) with 5a, which had been prepared by mixing both components in the absence of solvent, gave (R)-(+)-beta-lactam (9a) of 45% ee, although the 1:1 complex that had been prepared by recrystallization of the components from toluene gave (S)-(-)-9a of 100% ee. Mixing of powdered chiral (-)-3c crystal with a 2:1 inclusion complex of 5b and MeOH gave a new 1:1 complex of 5b and chiral (+)-3c, The inversion of the chirality of 3c in the solid state was studied by continuous measurements of CD spectra in Nujol mulls.
• Designs of host/guest molecular and crystal structures
  作者：Fumio Toda

  DOI：10.1016/0022-2860(95)09090-8

  日期：1996.1

  Abstract When an optically active host compound was mixed with an achiral guest compound in the solid state, host-guest inclusion crystals were formed by molecular movement and the achiral molecules became arranged in a chiral form in the inclusion crystals.

  摘要 当光学活性主体化合物与固态非手性客体化合物混合时，通过分子运动形成主客体包合物，非手性分子在包合物中以手性形式排列。