7,7-Diethoxy-bicyclo[2.2.1]hept-5-en-2,3-dicarbonsaeureanhydrid | 38680-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,7-Diethoxy-bicyclo[2.2.1]hept-5-en-2,3-dicarbonsaeureanhydrid
• 英文别名: 7,7-Diethoxy-bicyclo<2.2.1>hept-5-en-2,3-dicarbonsaeureanhydrid；7,7-Diaethoxy-5-norbornen-2,3-dicarbonsaeure-anhydrid
• CAS: 38680-03-4
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: UALREHFBNSDLSV-FIRGSJFUSA-N

物化性质

• 沸点：
  379.2±42.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7,7-Diethoxy-bicyclo[2.2.1]hept-5-en-2,3-dicarbonsaeureanhydrid 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 五氯化磷 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 58.0h， 生成 ((1R,2R,3S,4S)-7,7-Dichloro-3-hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol
  参考文献：
  名称：

  Synthesis and structure-activity relationships of a series of insecticidal dioxatricyclododecenes acting as the noncompetitive antagonist of GABAA receptors

  摘要：

  Chlorinated analogues of 5-substituted 2,3:8,7-endo-4,6-dioxatricyclo[7.2.1.0(2,8)]dodec-10-ene (DTD) and 2,3:8,7-endo-4,6-dioxa-5-thiatricyclo[7.1.1.0(2,8)]dodec-10-ene 5-oxide were prepared. With -CH2-, -CH(Me)-, and -S(O)- at the 5 position, the presence of chlorine atoms in the norbornene moiety was important in exerting toxic effects to houseflies, while with -CH(n-Pr)- and -CH(Ph-CN-4)- the introduction of chlorine atoms resulted in a loss of toxic activity. The effect of the presence of chlorine atoms on the potency in inhibiting [S-35]tert-butylbicyclophosphorothionate (TBPS) binding to rat brain membranes was found to be correlated to their insecticidal activity. A good correlation (r=0.807) was obtained between insecticidal activity and the potency in inhibiting [S-35]TBPS binding for 29 compounds, including known noncompetitive antagonists of GABA(A) receptors. The Scatchard analysis indicated that both types of analogues, 1,9,10,11,12,12-hexachloro-DTD and 5-(4-cyanophenyl)-DTD, act competitively at the TBPS binding site in the GABA-gated chloride channel. These two types of analogues, however, appear to interact with slightly different subsites within the TBPS binding site.

  DOI：

  10.1021/jf00035a059

文献信息

• A symmetry-driven approach toward the total synthesis of dodecahedrane
  作者：Jason V. Chari、Luca McDermott、Jacob E. Dander、Bryan J. Simmons、Neil K. Garg

  DOI：10.1016/j.tet.2022.133041

  日期：2022.11

  Herein, we describe our progress toward the total synthesis of dodecahedrane, a complex and highly symmetrical hydrocarbon that bears twelve fused rings arranged in a cage-like architecture. Central to our approach is a late-stage [2+2+2+2+2] polyene cyclization cascade, which is expected to construct five new bonds and ten new rings in a single transformation. Toward this end, we describe efforts

  在此，我们描述了十二面体全合成的进展，十二面体是一种复杂且高度对称的碳氢化合物，具有以笼状结构排列的十二个稠合环。我们方法的核心是后期[2+2+2+2+2]多烯环化级联，预计在一次转化中构建五个新键和十个新环。为此，我们描述了合成关键单体片段的努力，以及使用频哪醇偶联方法成功的二聚化研究。随后的研究包括尝试烯烃复分解重排级联以及成功的分子内光化学[2+2]反应。尽管详细阐述光环加成产物的尝试并未成功，但我们的研究提供了复杂二聚体支架的途径，并有望帮助指导我们未来的全合成研究。
• Absence of Heteroatom Kinetic Effects in p-Route to Carbocations
  作者：Alex Nickon、Stella S. Jones、Billy J. Parkhill

  DOI：10.3987/com-88-s100

  日期：——
• Roth, Wolfgang R.; Scholz, Bernhard P., Chemische Berichte, 1981, vol. 114, # 12, p. 3741 - 3750
  作者：Roth, Wolfgang R.、Scholz, Bernhard P.

  DOI：——

  日期：——