endo-2-(bicyclo<2.2.1>hept-5-en-2-yl)dioxolane | 43111-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: endo-2-(bicyclo<2.2.1>hept-5-en-2-yl)dioxolane
• 英文别名: 2-(2-Bicyclo[2.2.1]hept-5-enyl)-1,3-dioxolane
• CAS: 43111-72-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: BHNFGALCFATBNA-UHFFFAOYSA-N

物化性质

• 沸点：
  56-57 °C(Press: 1 Torr)
• 密度：
  1.0837 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  endo-2-(bicyclo<2.2.1>hept-5-en-2-yl)dioxolane 在 过氧乙酸 作用下， 以 氯仿 为溶剂， 以56%的产率得到cis-2-(5,6-epoxynorbornan-2-yl)-1,3-dioxolane
  参考文献：
  名称：

  Chemistry of Dioxacyclanes: XI. Synthesis and Properties of Unsaturated Derivatives of 1,3-Dioxolanes

  摘要：

  1,3-Dioxolanes were synthesized by reactions of 3-cyclohexenecarboxaldehyde and 5-norbornene2-endo-carboxaldehyde with 1,2-ethanedithiol and 3-(2-propenyloxy)- and 3-propoxy-1,2-propanediols, as well as of propionaldehyde, benzaldehyde, and trichloroacetaldehyde with the latter two thiols. Dichlorocarbene addition, bromination, and epoxidation of the ring C=C were accomplished, and activity of the resulting products as dienophiles in Dield-Alder reactions was assessed.

  DOI：

  10.1023/b:rugc.0000025512.21009.9e
• 作为产物：
  描述：

  2-乙烯基-1,3-二氧戊环 、 环戊二烯 在 四丁基高氯酸铵 、 lithium perchlorate 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到endo-2-(bicyclo<2.2.1>hept-5-en-2-yl)dioxolane
  参考文献：
  名称：

  An endo-selective ionic Diels-Alder reaction of .alpha.,.beta.-enone and .alpha.,.beta.-enal acetals catalyzed by electrogenerated acid

  摘要：

  DOI：

  10.1021/jo00299a050

文献信息

• Chiral Brønsted acid-catalyzed enantioselective ionic [2+4] cycloadditions
  作者：Alina Borovika、Pavel Nagorny

  DOI：10.1016/j.tet.2013.03.086

  日期：2013.7

  The first asymmetric chiral N-triflylphosphoramide-catalyzed ionic [2+4] cycloaddition reaction of unsaturated acetals is described. This reaction proceeds through the intermediacy of a vinyl oxocarbenium/chiral anion pair, and the chiral N-triflylphosphoramide anion controls the stereoselectivity of the cycloaddition step. Moderate enantioselectivities (up to 80:20 e.r.) have been obtained when α

  描述了不饱和缩醛的第一次不对称手性N-三氟磷酰胺催化的离子[2 + 4]环加成反应。该反应通过乙烯基氧碳鎓/手性阴离子对的中间体进行，并且手性N-三氟磷酰胺阴离子控制环加成步骤的立体选择性。当α，β-不饱和二氧戊环用作二亲物时，已获得中等对映选择性（高达80:20 er）。这些反应证明了对反离子配位特性和溶剂极性的强烈依赖性，而氧极性是氧碳鎓离子的行为特征。
• Kostikov, R. R.; Menchikov, L. G., Doklady Chemistry, 1984, vol. 276, p. 161 - 163
  作者：Kostikov, R. R.、Menchikov, L. G.

  DOI：——

  日期：——
• INOKUCHI, TSUTOMU;TANIGAWA, SIN-ICHI;TORII, SIGERU, J. ORG. CHEM., 55,(1990) N2, C. 3958-3961
  作者：INOKUCHI, TSUTOMU、TANIGAWA, SIN-ICHI、TORII, SIGERU

  DOI：——

  日期：——
• Chemistry of Dioxacyclanes: XI. Synthesis and Properties of Unsaturated Derivatives of 1,3-Dioxolanes
  作者：A. Kh. Kerimov

  DOI：10.1023/b:rugc.0000025512.21009.9e

  日期：2004.2

  1,3-Dioxolanes were synthesized by reactions of 3-cyclohexenecarboxaldehyde and 5-norbornene2-endo-carboxaldehyde with 1,2-ethanedithiol and 3-(2-propenyloxy)- and 3-propoxy-1,2-propanediols, as well as of propionaldehyde, benzaldehyde, and trichloroacetaldehyde with the latter two thiols. Dichlorocarbene addition, bromination, and epoxidation of the ring C=C were accomplished, and activity of the resulting products as dienophiles in Dield-Alder reactions was assessed.
• An endo-selective ionic Diels-Alder reaction of .alpha.,.beta.-enone and .alpha.,.beta.-enal acetals catalyzed by electrogenerated acid
  作者：Tsutomu Inokuchi、Sinichi Tanigawa、Sigeru Torii

  DOI：10.1021/jo00299a050

  日期：1990.6