(3Z,3aS,6aS)-3-(羟基亚甲基)-3,3A,4,6A-四氢-2H-环戊二烯并[b]呋喃-2-酮 | 194468-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (3Z,3aS,6aS)-3-(羟基亚甲基)-3,3A,4,6A-四氢-2H-环戊二烯并[b]呋喃-2-酮
• 英文名称: (3Z,3aS,6aS)-3-(hydroxymethylidene)-4,6a-dihydro-3aH-cyclopenta[b]furan-2-one
• CAS: 194468-85-4
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: QLKSEXJFLVWAOY-MBZKLQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3Z,3aS,6aS)-3-(羟基亚甲基)-3,3A,4,6A-四氢-2H-环戊二烯并[b]呋喃-2-酮 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， -30.0~500.0 ℃ 、1.33 Pa 条件下， 反应 17.75h， 生成 (3E,3aS,6aS)-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,6a-dihydro-3aH-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Use of Winterfeldt's template to control the C-2′ configuration in the synthesis of strigol-type compounds

  摘要：

  A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00077-5
• 作为产物：
  描述：

  (3aS,6R,6aR)-6-iodohexahydro-2H-cyclopenta[b]furan-2-one 在 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 生成 (3Z,3aS,6aS)-3-(羟基亚甲基)-3,3A,4,6A-四氢-2H-环戊二烯并[b]呋喃-2-酮
  参考文献：
  名称：

  Use of Winterfeldt's template to control the C-2′ configuration in the synthesis of strigol-type compounds

  摘要：

  A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00077-5

文献信息

• Attempted stereocontrol at C-2′ of strigol-type compounds by a Michael reaction/elimination approach
  作者：Susanne Röhrig、Lothar Hennig、Matthias Findeisen、Peter Welzel、Katja Frischmuth、Andreas Marx、Tanja Petrowitsch、Peter Koll、Dietrich Müller、Heike Mayer-Figge、William S. Sheldrick

  DOI：10.1016/s0040-4020(98)00076-3

  日期：1998.4

  By a Michael addition / nucleophilic substitution / elimination sequence the stereocontrol at C-2′ in strigol-typed compounds is in principle possible. However, the method is unsuitable for practical application since it has been shown that a stereolabile intermediate is involved.

  通过迈克尔加成/亲核取代/消除序列，在strigol型化合物中C-2'的立体控制原则上是可能的。然而，该方法不适用于实际应用，因为已经表明涉及立体不稳定的中间体。
• Strigol and sorgolactone synthetic studies use of Winterfeldt's template to control the C-2′ configuration
  作者：Susanne Röhrig、Lothar Hennig、Matthias Findeisen、Peter Welzel、Dietrich Müller

  DOI：10.1016/s0040-4039(97)01228-8

  日期：1997.8

  A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues. (C) 1997 Elsevier Science Ltd.
• Strigol synthetic studies the first synthetic approach that allows control of C-2′ configuration
  作者：Katja Frischmuth、Andreas Marx、Tanja Petrowitsch、Ulrich Wagner、Klaus Koerner、Silke Zimmermann、Heike Meuer、William S. Sheldrick、Peter Welzel

  DOI：10.1016/s0040-4039(00)73296-5

  日期：1994.7

  A phenylthio group has been used to control stereoselective bond formation at C-2'.