(1S,4R,8S)-4-hydroxy-3-oxo-8-[(4S)-4-phenyloxazolidin-2-one-3-carbonyl]-2-oxabicyclo[2.2.2]oct-5-ene | 203627-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1S,4R,8S)-4-hydroxy-3-oxo-8-[(4S)-4-phenyloxazolidin-2-one-3-carbonyl]-2-oxabicyclo[2.2.2]oct-5-ene
• 英文别名: (4R)-3-[(1R,4S,5R)-4-hydroxy-3-oxo-2-oxabicyclo[2.2.2]oct-7-ene-5-carbonyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 203627-46-7
• 化学式: C₁₇H₁₅NO₆
• 分子量: 329.309
• InChiKey: YGYMTVFPQQFBMR-MRHIQRDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,4R,8S)-4-hydroxy-3-oxo-8-[(4S)-4-phenyloxazolidin-2-one-3-carbonyl]-2-oxabicyclo[2.2.2]oct-5-ene 在 咪唑 、 sodium periodate 、 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.83h， 生成 (3R,4S,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-3-trimethylsilanyloxy-4-trimethylsilanyloxymethyl-cyclohexene
  参考文献：
  名称：

  Asymmetric synthesis of (−)- and (+)-eutipoxide B using a base-catalyzed Diels–Alder reaction

  摘要：

  The asymmetric synthesis of eutipoxide B, a metabolite of the phytopathogenic fungus Eutypa lata, is described. Quick and efficient synthesis of each enantiomer was achieved through base-catalyzed asymmetric Diels-Alder reactions with 3-hydroxy-2-pyrone and chiral acrylates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00032-1
• 作为产物：
  描述：

  3-羟基-2-吡喃酮 、 (R)-3-acryloyl-4-phenyloxazolidin-2-one 在 辛可尼丁 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 以82%的产率得到(1S,4R,8S)-4-hydroxy-3-oxo-8-[(4S)-4-phenyloxazolidin-2-one-3-carbonyl]-2-oxabicyclo[2.2.2]oct-5-ene
  参考文献：
  名称：

  Asymmetric synthesis of (−)- and (+)-eutipoxide B using a base-catalyzed Diels–Alder reaction

  摘要：

  The asymmetric synthesis of eutipoxide B, a metabolite of the phytopathogenic fungus Eutypa lata, is described. Quick and efficient synthesis of each enantiomer was achieved through base-catalyzed asymmetric Diels-Alder reactions with 3-hydroxy-2-pyrone and chiral acrylates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00032-1

文献信息

• Asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral acrylate derivatives
  作者：Hiroaki Okamura、Katsuki Morishige、Tetsuo Iwagawa、Munehiro Nakatani

  DOI：10.1016/s0040-4039(97)10843-7

  日期：1998.3

  In the presence of a cinchona alkaloid as a catalyst, the Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral N-acryloyl oxazolidinone afforded a bicyclolactone adduct with high diastereoselectivities (up to 95%de) in almost quantitative yield.

  在金鸡纳生物碱作为催化剂的存在下，3-羟基-2-吡喃酮与手性N-丙烯酰基恶唑烷酮的狄尔斯-阿尔德反应以几乎定量的产率提供了具有高非对映选择性（高达95％de）的双环内酯加合物。
• Asymmetric synthesis of (−)- and (+)-eutipoxide B using a base-catalyzed Diels–Alder reaction
  作者：Hideki Shimizu、Hiroaki Okamura、Tetsuo Iwagawa、Munehiro Nakatani

  DOI：10.1016/s0040-4020(01)00032-1

  日期：2001.3

  The asymmetric synthesis of eutipoxide B, a metabolite of the phytopathogenic fungus Eutypa lata, is described. Quick and efficient synthesis of each enantiomer was achieved through base-catalyzed asymmetric Diels-Alder reactions with 3-hydroxy-2-pyrone and chiral acrylates. (C) 2001 Elsevier Science Ltd. All rights reserved.