N-((R)-3-oxo-1,3-diphenylpropyl)benzamide | 91875-49-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-((R)-3-oxo-1,3-diphenylpropyl)benzamide
• 英文别名: (R)-N-(3-oxo-1,3-diphenylpropyl)benzamide；(R)-3-benzoylamino-1,3-diphenyl-propan-1-one；(R)-3-Benzoylamino-1,3-diphenyl-propan-1-on；N-[(1R)-3-oxo-1,3-diphenylpropyl]benzamide
• CAS: 91875-49-9
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: QTBKOGLJPINUKJ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((R)-3-oxo-1,3-diphenylpropyl)benzamide 在 sodium dihydrogenphosphate 、 硫酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 26.0h， 生成 (R)-3-benzamido-3-phenylpropanoic acid methyl ester
  参考文献：
  名称：

  手性布朗斯台德酸的高底物/催化剂有机催化作用，用于对映选择性氮杂-烯型反应。

  摘要：

  DOI：

  10.1002/anie.200503477
• 作为产物：
  描述：

  N-[甲氧基(苯基)甲基]苯甲酰胺 在 (R)-[3-(9-anthryl)-2-hydroxynaphth-1-yl]2 cyclic phosphate 、 potassium carbonate 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 N-((R)-3-oxo-1,3-diphenylpropyl)benzamide
  参考文献：
  名称：

  手性布朗斯台德酸的高底物/催化剂有机催化作用，用于对映选择性氮杂-烯型反应。

  摘要：

  DOI：

  10.1002/anie.200503477

文献信息

• BIS-PHOSPHATE COMPOUND AND ASYMMETRIC REACTION USING THE SAME
  申请人：Terada Masahiro

  公开号：US20120330038A1

  公开（公告）日：2012-12-27

  A novel bis-phosphate compound is provided which can be applied to a wide range of reactive substrates and reactions as an asymmetric reaction catalyst and can realize an asymmetric reaction affording a high yield and a high enantiomeric excess. The bis-phosphate compound has a tetraaryl skeleton represented by General Formula (1). In an asymmetric reaction, an amidodiene and an unsaturated aldehyde compound are reacted with each other in the presence of the optically active bis-phosphate compound to give an optically active amidoaldehyde. The invention allows a reaction such as an asymmetric Diels-Alder reaction to proceed efficiently, which has been difficult with conventional mono-phosphate compounds. Thus, the invention enables an industrially feasible method for the production of optically active amidoaldehydes, optically active β-amino acid derivatives, optically active diamine compounds, optically active pyrrolidine derivatives and optically active dihydropyran derivatives which are useful as products such as medicines, agricultural chemicals and chemical products as well as synthesis intermediates for such products.

  提供了一种新型的双磷酸盐化合物，可应用于广泛的反应底物和反应作为不对称反应催化剂，并且可以实现产率高和对映体过量高的不对称反应。该双磷酸盐化合物具有由通用式（1）表示的四芳基骨架。在不对称反应中，存在光学活性的双磷酸盐化合物的情况下，通过使酰胺二烯和不饱和醛化合物相互反应，得到光学活性的酰胺醛。该发明使得像不对称Diels-Alder反应这样的反应能够高效进行，而传统的单磷酸盐化合物很难实现。因此，该发明实现了一种工业上可行的方法，用于生产用作药品、农药和化工产品以及用于这些产品的合成中间体的光学活性酰胺醛、光学活性β-氨基酸衍生物、光学活性二胺化合物、光学活性吡咯烷衍生物和光学活性二氢吡喃衍生物。
• Asymmetric synthesis of 4H-1,3-oxazines: enantioselective reductive cyclization of N-acylated β-amino enones with trichlorosilane catalyzed by chiral Lewis bases
  作者：Masaharu Sugiura、Mako Kumahara、Makoto Nakajima

  DOI：10.1039/b905102c

  日期：——

  N-Acylated beta-amino enones reductively cyclize by treatment with trichlorosilane and a chiral Lewis base catalyst to afford optically active 4H-1,3-oxazines, which can be transformed to other chiral compounds without racemization.

  通过用三氯硅烷和手性路易斯碱催化剂处理，N-酰化的β-氨基烯酮还原环化，得到旋光的4H-1,3-恶嗪，可以将其转化为其他手性化合物而无需外消旋化。
• Metal-Free Chiral Phosphoric Acid or Chiral Metal Phosphate as Active Catalyst in the Activation of N-Acyl Aldimines
  作者：Masahiro Terada、Kyohei Kanomata

  DOI：10.1055/s-0030-1260545

  日期：2011.6

  Whether metal-free chiral phosphoric acid or chiral metal phosphate functions as an active catalyst was confirmed in three reactions. In the aza-Friedel-Crafts and aza-ene-type reactions, a metal-free chiral phosphoric acid, namely, a chiral Brønsted acid, was verified to be the active catalyst. In contrast, the substitution ­reaction of α-diazoacetate with aldimine was accelerated by a salt-containing chiral phosphoric acid and hence chiral metal phosphate presumably functioned as an active catalyst.

  在三种反应中确认了无金属手性磷酸或手性金属磷酸作为活性催化剂的作用。在 aza-Friedel-Crafts 和 aza-ene 型反应中，无金属手性磷酸（即手性 Brønsted 酸）被验证为活性催化剂。相反，α-二氮乙酸与醛亚胺的取代反应则是由含盐的手性磷酸加速的，因此手性金属磷酸很可能作为活性催化剂发挥作用。
• Asymmetric Amplification in Phosphoric Acid Catalyzed Reactions
  作者：Nan Li、Xiao-Hua Chen、Shi-Ming Zhou、Shi-Wei Luo、Jin Song、Lei Ren、Liu-Zhu Gong

  DOI：10.1002/anie.201001723

  日期：2010.8.23

  reactions catalyzed by phosphoric acids arose from the formation of less soluble supramolecular structures (see scheme; O red, P yellow, C gray, H white) of the racemic phosphoric acids that participate in hydrogen bonds with the crystalline water molecules. The finding shows that highly enantioselective reactions can be observed by using non‐optically pure phosphoric acids.

  一个 EE 安培：不对称扩增在由磷酸类催化反应从较少溶解的超分子结构的形成产生（参见方案; O型红，P黄色，C灰色，H白）的参与氢键与结晶外消旋磷酸水分子。该发现表明，使用非光学纯的磷酸可以观察到高度对映选择性的反应。
• Pulmonary cryptococcosis and Capillaria aerophila infection in an FIV-positive cat
  作者：VR BARRS、P. MARTIN、RG NICOLL、JA BEATTY、R. MALIK

  DOI：10.1111/j.1751-0813.2000.tb10581.x

  日期：2000.3

  A 12‐year‐old, FIV‐positive, domestic longhair cat was presented with a history of sneezing and coughing during the previous seven months. On thoracic radiographs, a prominent bronchial pattern and three focal, opacified nodules were seen. Cytology of bronchoalveolar lavage fluid demonstrated spherical, capsulate, narrow‐necked, budding yeasts within macrophages. Culture of the fluid yielded a heavy growth of Cryptococcus neoformans var neoformans. The serum latex cryptococcal antigen agglutination test titre was 158. The cat was treated with itraconazole and the cough resolved over a 5‐month period but then recurred. Repeat thoracic radiographs showed resolution of the pulmonary nodules but a persistent bronchial pattern. Adult nematodes and ova with morphology characteristic of Capillaria aerophila were seen in bronchoalveolar lavage fluid and no yeasts were cultured from the fluid. The cryptococcal titre was zero. The lungworm infection was treated successfully with abamectin and the cough resolved. Immunosuppression related to FIV infection may have predisposed this cat to sequential respiratory tract infections.