(4R)-4-苄基-3-[(2R)-2-苯基丙酰基]恶唑烷-2-酮 | 214492-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4R)-4-苄基-3-[(2R)-2-苯基丙酰基]恶唑烷-2-酮
• 英文名称: (4R)-4-benzyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2R)-2-phenylpropanoyl]-1,3-oxazolidin-2-one
• CAS: 214492-00-9
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: BXUPGDHRJVQFMQ-RHSMWYFYSA-N

物化性质

• 沸点：
  487.7±24.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  (4R)-4-苄基-3-[(2R)-2-苯基丙酰基]恶唑烷-2-酮 在 lithium aluminium tetrahydride 、 四溴化碳 、 magnesium 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Potent Kv1.3 inhibitors from correolide—modification of the C18 position

  摘要：

  Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.058
• 作为产物：
  描述：

  2,2-dimethylpropanoicphenylacetic anhydride 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (4R)-4-苄基-3-[(2R)-2-苯基丙酰基]恶唑烷-2-酮
  参考文献：
  名称：

  Potent Kv1.3 inhibitors from correolide—modification of the C18 position

  摘要：

  Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.058

文献信息

• A new, economical, practical and racemization-free method for the reductive removal of 2-oxazolidinones from N-acyloxazolidinones with sodium borohydride
  作者：Mahavir Prashad、Denis Har、Hong-Yong Kim、Oljan Repic

  DOI：10.1016/s0040-4039(98)01521-4

  日期：1998.9

  A new, economical, practical and racemization-free method for the reductive removal of 2-oxazolidinones by a reduction of N-acyloxazolidinones with sodium borohydride in THF and water is described.

  描述了一种新的，经济的，实用的和无消旋的方法，该方法通过在THF和水中用硼氢化钠还原N-酰基恶唑烷酮来还原去除2-恶唑烷酮。
• Parallel kinetic resolution of racemic oxazolidinones using quasi-enantiomeric active esters
  作者：Ewan Boyd、Elliot Coulbeck、Gregory S. Coumbarides、Sameer Chavda、Marco Dingjan、Jason Eames、Anthony Flinn、Majid Motevalli、Julian Northen、Yonas Yohannes

  DOI：10.1016/j.tetasy.2007.10.009

  日期：2007.10

  Racemic Evans' oxazolidinones were efficiently resolved using a combination of quasi-enantiomeric profens. The levels of stereocontrol were high, leading to products with predictable configurations. (c) 2007 Elsevier Ltd. All rights reserved.