4,4-dimethyl-cis-3-oxabicyclo[4.3.0]nonan-2-one | 17351-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 4,4-dimethyl-cis-3-oxabicyclo[4.3.0]nonan-2-one
• 英文别名: 3,3-dimethyloctahydroisobenzofuran-1-one；(3aR,7aS)-3,3-dimethyl-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1-one
• CAS: 17351-10-9；17351-14-3；40066-17-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: UPMLSDVHIQUHDV-JGVFFNPUSA-N

物化性质

• 沸点：
  259.4±8.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  4,4-dimethyl-cis-3-oxabicyclo[4.3.0]nonan-2-one 在 zinc(II) iodide 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 、 丙酮 为溶剂， 反应 15.0h， 生成 2-(tert-Butyl-dimethyl-silanyloxy)-4-((3aS,7aS)-1,1-dimethyl-3-oxo-hexahydro-isobenzofuran-3a-yl)-butyronitrile
  参考文献：
  名称：

  有效的立体控制合成的达米辛ABC亚基

  摘要：

  通过利用内酯羰基阴离子等价物对内酯羰基进行酰化，可以有效地以完全立体控制的方式组装强效昆虫拒食性达明素的ABC网络。

  DOI：

  10.1016/0040-4039(94)88451-x
• 作为产物：
  描述：

  (3aR,7aR)-1,1-Dimethyl-3-oxo-hexahydro-isobenzofuran-3a-carboxylic acid methyl ester 在 aluminum oxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 4,4-dimethyl-cis-3-oxabicyclo[4.3.0]nonan-2-one
  参考文献：
  名称：

  Mn（III）活化酸的分子内酯环化

  摘要：

  乙酸锰（III）将活化羧酸的分子内酯环化到烯烃上，生成双环[3.3.0]和[4.3.O]内酯。

  DOI：

  10.1016/s0040-4039(00)89244-8

文献信息

• Total Synthesis of Dumsin. 1. Retrosynthetic Strategy and the Elaboration of Key Intermediates from (−)-Bornyl Acetate
  作者：Leo A. Paquette、Fang-Tsao Hong

  DOI：10.1021/jo0301346

  日期：2003.9.1

  An intramolecular anionic oxy-Cope rearrangement (44 --> 46) serves as the key step in a synthetic approach to the insect antifeedant dumsin. Initial investigations clarified the manner in which (--)-bornyl acetate may be transformed into the exo-norbornenol 44. Two routes were developed to advance beyond 46. The first involved acetal 51 as a matrix that was expected to allow the elaboration of rings

  分子内阴离子oxy-Cope重排（44-> 46）是昆虫抗饲料dumsin合成方法中的关键步骤。初步研究阐明了乙酸（-）乙酸冰片酯可转化为外降冰片烯醇44的方式。开发了两种方法以超越46。首先涉及乙缩醛51作为基质，预期可精制环D和E。第二个计划将46中的环戊烯环的氧化反应推迟到分子构建的后期。后面的实验构成了协议的基础，该协议导致成功获取以108和114为代表的酮醛。
• Fungistatic Activity of Bicyclo[4.3.0]-γ-lactones
  作者：Teresa Olejniczak、Filip Boratyński、Agata Białońska

  DOI：10.1021/jf105019u

  日期：2011.6.8

  Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC50 values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo-[4.3.0]nonan-2-one (3c), IC50 = 30.1 mu g/mL (0.10 mu M/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one (3b), IC50 = 72.2 mu g/mL (0.47 mu M/mL), toward F. oxysporum AM 13.
• 1-Substitutedvinyl-1-phthalanpropylamines as potential antidepressant agents
  作者：Francis J. McEvoy、Robert F. R. Church、E. N. Greenblatt、George R. Allen

  DOI：10.1021/jm00281a006

  日期：1972.11
• A convenient route to 1,4-monoprotected dialdehydes, 1,4-ketoaldehydes, γ-lactols and γ-lactones through radical alkylation of α,β-unsaturated aldehydes in organic and organic-aqueous media
  作者：Daniele Dondi、Ilaria Caprioli、Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1016/s0040-4020(02)01659-9

  日期：2003.2

  alpha,beta-Unsaturated aldehydes were smoothly alkylated by radicals generated through photosensitised hydrogen abstraction of benzophenone. In this way, and by using 1,3-dioxolane as radical precursor, monoprotected 1,4-dialdehydes were obtained from crotonaldehyde, 2-hexenal, 4-methyl-2-pentenal and cyclohexenearboxyaldehyde in a moderate yield, and in a low yield from beta-aryl-alpha,beta-unsaturated aldehydes. With 2-alkyl-1,3-dioxolanes, monoprotected 1,4-ketoaldehydes were analogously prepared. By using methanol, ethanol and isopropanol as radical precursors gamma-lactols were likewise obtained from the above aliphatic aldehydes. These single-step syntheses compared favorably with multi-step approaches previously proposed for some of these compounds. The lactols were conveniently oxidized to the corresponding gamma-lactones. An alternative to the photosensitisation in organic medium was the use of mixed aqueous-organic solvent and a hydrosoluble photosensitiser (benzophenone disodium disulfonate was prepared for this purpose and successfully used), which allowed a more convenient work up. (C) 2003 Elsevier Science Ltd. All rights reserved.
• ERNST, A. B.;FRISTAD, W. E., TETRAHEDRON LETT., 1985, 26, N 32, 3761-3764
  作者：ERNST, A. B.、FRISTAD, W. E.

  DOI：——

  日期：——