3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one
• 英文别名: (3aS,7aS)-3a,4,7,7a-tetrahydro-3H-1-benzofuran-2-one
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: PPASVOQVTFYTSL-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (3aS,7aS)-hexahydrobenzofuran-2(3H)-one
  参考文献：
  名称：

  Kosugi, Hiroshi; Tagami, Katsuya; Takahashi, Akira, Journal of the Chemical Society. Perkin transactions I, 1989, p. 935 - 943

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,7aR)-7a-(4-methylphenyl)sulfanyl-3,3a,4,7-tetrahydro-1-benzofuran-2-one 生成 3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one
  参考文献：
  名称：

  KOSUGI, HIROSHI;TAGAMI, KATSUYA;TAKAHASHI, AKIRA;KANNA, HIROSHI;UDA, HISA+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 935-943

  摘要：

  DOI：

文献信息

• Oxidative Cyclizations in a Nonpolar Solvent Using Molecular Oxygen and Studies on the Stereochemistry of Oxypalladation
  作者：Raissa M. Trend、Yeeman K. Ramtohul、Brian M. Stoltz

  DOI：10.1021/ja055534k

  日期：2005.12.1

  illustrates the range of reactivity available from various Pd(II) salts under differing conditions. Alcohols can form both fused and spirocyclic ring systems, depending on the position of the olefin relative to the tethered alcohol; the same is true of the acid derivatives. The racemic conditions served as a platform for the development of an enantioselective reaction. Experiments with stereospecifically

  在非极性溶剂（甲苯）中，在分子氧作为唯一化学计量氧化剂的存在下，钯 (II) 和吡啶催化各种杂原子亲核试剂氧化环化到未活化的烯烃上。许多 N-连接的钯配合物的反应性研究表明螯合配体减慢反应。几乎相同的条件适用于五种不同类型的亲核试剂：酚类、伯醇、羧酸、乙烯酸和酰胺。富电子酚类是极好的底物，并且可以容忍多种烯烃取代模式。伯醇会发生氧化环化反应而没有明显氧化成醛，这一事实说明了在不同条件下可从各种 Pd(II) 盐获得的反应性范围。醇可以形成稠环和螺环系统，这取决于烯烃相对于束缚醇的位置；酸衍生物也是如此。外消旋条件作为发展对映选择性反应的平台。立体定向氘代伯醇底物的实验排除了涉及抗氧化钯的“Wacker 型”机制，并表明该反应通过单齿和双齿配体的同步氧化钯进行。相比之下，氘标记的羧酸底物的环化会发生抗氧化钯。立体定向氘代伯醇底物的实验排除了涉及抗氧化钯的“Wacker 型”机制，并表明该反应
• 10.1002/(sici)1099-0690(199801)1998:1<57::aid-ejoc57<3.0.co;2-w
  作者：Audran, Gerard、Mori, Kenji

  DOI：10.1002/(sici)1099-0690(199801)1998:1<57::aid-ejoc57<3.0.co;2-w

  日期：——
• Synthesis and absolute configuration of phyllanthurinolactone, the leaf-closing factor of a nyctinastic plant, Phyllanthus urinaria L.
  作者：Kenji Mori、Gérard Audran、Yoshiaki Nakahara、Masahiko Bando、Masaru Kido

  DOI：10.1016/s0040-4039(96)02375-1

  日期：1997.1

  Phyllanthurinolactone (1) and its diastereoisomer 19 were synthesized, only the former of which was bioactive as the leaf-closing factor of Phyllanthus urinaria L. X-ray analysis of the tetraacetylglucoside 18 was executed, and the absolute configuration of 1 was determined as 6S, 7aR. (C) 1997, Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of deoxycarbaheptopyranose derivatives: 5a-carba-6-deoxy-α-dl-galacto-heptopyranose and 5a-carba-6-deoxy-α-dl-gulo-heptopyranose
  作者：Nurhan Horasan Kishali、Dilem Doğan、Ertan Şahin、Aslihan Gunel、Yunus Kara、Metin Balci

  DOI：10.1016/j.tet.2010.11.102

  日期：2011.2

  Two new deoxycarbaheptopyranoses, 5a-carba-6-deoxy-alpha-DL-galacto-heptopyranose and 5a-carba-6-deoxy-alpha-DL-gulo-heptopyranose were prepared starting from cyclohexa-1,4-diene. The addition of dichloroketene to cyclohexa-1,4-diene followed by the subsequent reductive elimination and Baeyer-Villiger oxidation in turn led to the formation of a bicyclic lactone. Reduction of the lactone moiety followed by acetylation gave a diacetate with cis-configuration. The introduction of additional acetate functionality into the molecule was achieved by singlet oxygen ene-reaction. The formed hydroperoxide was reduced and then acetylated. The triacetate was further functionalized either by direct cis-hydroxylation using OsO4 or by epoxidation followed by a ring-opening reaction to give the title heptopyranose derivatives. One of the synthesized molecules, galacto-heptopyranose exhibited enzyme specific inhibition against alpha-glycosidase. On the other hand, they did not show any inhibition for alpha-amylase. However, both compounds, gulo-heptopyranose and galacto-heptopyranose increased the activity of alpha-amylase. (C) 2010 Elsevier Ltd. All rights reserved.
• Unusual Facial Selectivity in the Cycloaddition of Singlet Oxygen to a Simple Cyclic Diene¹
  作者：Kelly M. Davis、Barry K. Carpenter

  DOI：10.1021/jo9604292

  日期：1996.1.1

  Syntheses of 5-isopropyl-1,3-cyclohexadiene and syn-5-isopropyl-2,3-dioxabicyclo[2.2.2]octane, by routes that would allow completely diastereoselective introduction of deuterium labels, are described. The reaction of the isopropyl cyclohexadiene with singlet oxygen is shown to give an endoperoxide that is derived by preferential attack on the more sterically hindered face of the diene, A possible mechanistic explanation of this result is that the attack from the less hindered face leads to ''ene'' reaction rather than endoperoxide formation, However, this mechanism would require that the ''ene'' reaction and cycloaddition proceed via a common intermediate-presumably a perepoxide.