3-methyl-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-2-one | 949158-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: 3-methyl-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-2-one
• 英文别名: 3-Methyl-4,5,7,7a-tetrahydrofuro[2,3-c]pyran-2-one；3-methyl-4,5,7,7a-tetrahydrofuro[2,3-c]pyran-2-one
• CAS: 949158-56-9
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: RIVCCIQLBBZDNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基2H-呋喃并[2,3-c]吡喃-2-酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以55%的产率得到3-methyl-4,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-2-one
  参考文献：
  名称：

  Exploring the molecular mechanism of karrikins and strigolactones

  摘要：

  Karrikins and strigolactones are novel plant growth regulators that contain similar molecular features, but very little is known about how they elicit responses in plants. A tentative molecular mechanism has previously been proposed involving a Michael-type addition for both compounds. Through structure-activity studies with karrikins, we now propose an alternative mechanism for karrikin and strigolactone mode of action that involves hydrolysis of the butenolide ring. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.016

文献信息

• Cu(II)-Catalyzed Acylation by Thiol Esters Under Neutral Conditions: Tandem Acylation-Wittig Reaction Leading to a One-Pot Synthesis of Butenolides
  作者：Kazumasa Matsuo、Mitsuru Shindo

  DOI：10.1021/ol102407k

  日期：2010.11.19

  The first catalytic acylation of alcohols with a thiol ester present in Wittig reagents under neutral conditions catalyzed by the Cu(II) salt through a push−pull mechanism is reported. Furthermore, a new methodology for the one-pot lactonization of acyloins by a copper catalyst is developed. The synthetic utility of this method for the synthesis of natural products is shown.

  据报道，在中性条件下，Cu（II）盐通过推挽机制催化了醇与Wittig试剂中存在的硫醇酯的首次催化酰化作用。此外，开发了一种新的方法，用于通过铜催化剂对酰基辅酶进行单锅内酯化。显示了该方法用于合成天然产物的合成效用。
• Exploring the molecular mechanism of karrikins and strigolactones
  作者：Adrian Scaffidi、Mark T. Waters、Charles S. Bond、Kingsley W. Dixon、Steven M. Smith、Emilio L. Ghisalberti、Gavin R. Flematti

  DOI：10.1016/j.bmcl.2012.04.016

  日期：2012.6

  Karrikins and strigolactones are novel plant growth regulators that contain similar molecular features, but very little is known about how they elicit responses in plants. A tentative molecular mechanism has previously been proposed involving a Michael-type addition for both compounds. Through structure-activity studies with karrikins, we now propose an alternative mechanism for karrikin and strigolactone mode of action that involves hydrolysis of the butenolide ring. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.