(R)-3-[(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one | 1260083-80-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-3-[(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one
• 英文别名: (4R)-3-[(3R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1260083-80-4
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: XSCHZYUSGHUWBS-KDOFPFPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-[(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one 在 lithium hydroxide monohydrate 、 双氧水 作用下， 以 水 为溶剂， 以97%的产率得到(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid
  参考文献：
  名称：

  （+）-heliannuol D的高效全合成

  摘要：

  通过采用非对映选择性共轭加成反应生成叔苄基立体异构中心并通过有效的一锅简单地组装官能化的环氧庚烷骨架，可在14个步骤中以14％的总产率完成（+）-helnunuol D的有效全合成改造程序为关键步骤。

  DOI：

  10.1016/j.tetasy.2010.08.018
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基-4-甲基苯 、 (R)-3-acryloyl-4-phenyloxazolidin-2-one 在 copper(I) bromide dimethylsulfide complex 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 (R)-3-[(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Enantioselective total synthesis of heliespirone B

  摘要：

  The first enantiocontrolled total synthesis of heliespirone B has been accomplished employing a biomimetic intramolecular oxy-Michael reaction followed by the regio- and diastereoselective reduction of the carbonyl function as key steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.115

文献信息

• Enantioselective syntheses of the assigned structures of the helibisabonols A and B
  作者：Akari Miyawaki、Mayu Osaka、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tet.2011.03.064

  日期：2011.9

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.
• An efficient total synthesis of (+)-heliannuol D
  作者：Mayu Osaka、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetasy.2010.08.018

  日期：2010.10

  An efficient total synthesis of (+)-heliannuol D was accomplished in 14 steps and in 12% overall yield by employing a diastereoselective conjugate addition reaction to create a tertiary benzylic stereogenic center and simple assembly of the functionalized oxepane framework by an efficient one-pot transformation procedure as the key steps.

  通过采用非对映选择性共轭加成反应生成叔苄基立体异构中心并通过有效的一锅简单地组装官能化的环氧庚烷骨架，可在14个步骤中以14％的总产率完成（+）-helnunuol D的有效全合成改造程序为关键步骤。
• Enantioselective total synthesis of heliespirone B
  作者：Akari Miyawaki、Yuki Manabe、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetlet.2011.12.115

  日期：2012.3

  The first enantiocontrolled total synthesis of heliespirone B has been accomplished employing a biomimetic intramolecular oxy-Michael reaction followed by the regio- and diastereoselective reduction of the carbonyl function as key steps. (C) 2012 Elsevier Ltd. All rights reserved.