(R)-4-benzyl-3-cinnamoyloxazolidin-2-one | 143167-61-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R)-4-benzyl-3-cinnamoyloxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one
• CAS: 143167-61-7
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: JWRBSVRDVDBQOA-QGZVFWFLSA-N

物化性质

• 沸点：
  448.4±38.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-cinnamoyloxazolidin-2-one 在 氯化二乙基铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (4R)-4-benzyl-3-[(9R,10R)-3,3-dimethyl-10-phenyl-1,5-dioxaspiro[5.5]undecane-9-carbonyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Discovery and optimization of orally active cyclohexane-based prolylcarboxypeptidase (PrCP) inhibitors

  摘要：

  The synthesis, SAR, binding affinities and pharmacokinetic profiles are described for a series of cyclohexane- based prolylcarboxypeptidase (PrCP) inhibitors discovered by high throughput screening. Compounds show high levels of ex vivo target engagement in mouse plasma 20 h post oral dose. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.094
• 作为产物：
  描述：

  (R)-4-苄基-2-噁唑烷酮 、 肉桂酸 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-4-benzyl-3-cinnamoyloxazolidin-2-one
  参考文献：
  名称：

  Discovery and optimization of orally active cyclohexane-based prolylcarboxypeptidase (PrCP) inhibitors

  摘要：

  The synthesis, SAR, binding affinities and pharmacokinetic profiles are described for a series of cyclohexane- based prolylcarboxypeptidase (PrCP) inhibitors discovered by high throughput screening. Compounds show high levels of ex vivo target engagement in mouse plasma 20 h post oral dose. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.094

文献信息

• Fluorinated Sulfinates as Source of Alkyl Radicals in the Photo‐Enantiocontrolled β‐Functionalization of Enals
  作者：Ricardo I. Rodríguez、Marina Sicignano、José Alemán

  DOI：10.1002/anie.202112632

  日期：2022.2.21

  use of gem-difluoro sulfinates in visible-light photocatalysis for the construction of new C−C bonds in a chiral fashion is presented. This was tackled by rerouting the chemical pathway of alkyl sulfonyl radicals from traditional sulfonylation to alkylation performance. The efficacy of these sulfinates for assisting SO2 extrusion is shown by allowing the installation of CF2-bearing scaffolds, a modern

  介绍了宝石-二氟亚磺酸盐在可见光光催化中前所未有的用途，用于以手性方式构建新的 C-C 键。这是通过将烷基磺酰基自由基的化学途径从传统的磺酰化重新路由到烷基化性能来解决的。这些亚磺酸盐有助于 SO 2挤出的功效通过允许安装带有 CF 2的支架来显示，这是制药领域的一项现代任务。
• Facile Formation of <i>N</i>-Acyl-oxazolidinone Derivatives Using Acid Fluorides
  作者：Corinna S. Schindler、Patrik M. Forster、Erick M. Carreira

  DOI：10.1021/ol1016977

  日期：2010.9.17

  A mild method is presented for the formation of N-acylated oxazolidinones that employs acid fluorides and mild bases, such as (i)Pr(2)NEt and NEt(3). Optimized reaction conditions for two types of substrates have been developed utilizing either the oxazolidinone itself or the corresponding in situ generated O-silyloxazolidinones resulting in the formation of the desired N-acylated products in high yields of up to 98%.
• (S)-N-(5-Chlorothiophene-2-sulfonyl)-β,β-diethylalaninol a Notch-1-sparing γ-secretase inhibitor
  作者：Derek C. Cole、Joseph R. Stock、Anthony F. Kreft、Madelene Antane、Suzan H. Aschmies、Kevin P. Atchison、David S. Casebier、Thomas A. Comery、George Diamantidis、John W. Ellingboe、Boyd L. Harrison、Yun Hu、Mei Jin、Dennis M. Kubrak、Peimin Lu、Charles W. Mann、Robert L. Martone、William J. Moore、Aram Oganesian、David R. Riddell、June Sonnenberg-Reines、Shaiu-Ching Sun、Erik Wagner、Zheng Wang、Kevin R. Woller、Zheng Xu、Hua Zhou、J. Steven Jacobsen

  DOI：10.1016/j.bmcl.2008.11.116

  日期：2009.2

  Accumulation of beta-amyloid (A beta), produced by the proteolytic cleavage of amyloid precursor protein (APP) by beta- and gamma-secretase, is widely believed to be associated with Alzheimer's disease (AD). Research around the high-throughput screening hit (S)-4-chlorophenylsulfonyl isoleucinol led to the identification of the Notch-1-sparing (9.5-fold) gamma-secretase inhibitor (S)-N-(5-chlorothiophene-2-sulfonyl)-beta,beta-diethylalaninol 7.b.2 (A beta (40/42) EC50 = 28 nM), which is efficacious in reduction of A beta production in vivo. (C) 2008 Elsevier Ltd. All rights reserved.
• Discovery and optimization of orally active cyclohexane-based prolylcarboxypeptidase (PrCP) inhibitors
  作者：John S. Debenham、Thomas H. Graham、Andreas Verras、Yong Zhang、Matthew J. Clements、Jeffrey T. Kuethe、Christina Madsen-Duggan、Wensheng Liu、Urmi R. Bhatt、Dunlu Chen、Qing Chen、Margarita Garcia-Calvo、Wayne M. Geissler、Huaibing He、Xiaohua Li、JeanMarie Lisnock、Zhu Shen、Xinchun Tong、Elaine C. Tung、Judyann Wiltsie、Suoyu Xu、Jeffrey J. Hale、Shirly Pinto、Dong-Ming Shen

  DOI：10.1016/j.bmcl.2013.09.094

  日期：2013.12

  The synthesis, SAR, binding affinities and pharmacokinetic profiles are described for a series of cyclohexane- based prolylcarboxypeptidase (PrCP) inhibitors discovered by high throughput screening. Compounds show high levels of ex vivo target engagement in mouse plasma 20 h post oral dose. (C) 2013 Elsevier Ltd. All rights reserved.