endo-3-chloro-exo-2-phenylselenobicyclo<2.2.1>heptane | 70303-01-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: endo-3-chloro-exo-2-phenylselenobicyclo<2.2.1>heptane
• 英文别名: trans-2-chloro-3-(phenylseleno)bicyclo<2.2.1>heptane；exo-2-phenylseleno-endo-3-chlorobicyclo<2.2.1>heptane；endo-2-chloro-exo-3-phenylselanylbicyclo[2.2.1]heptane；(1S,2S,3S,4R)-2-chloro-3-phenylselanylbicyclo[2.2.1]heptane
• CAS: 70303-01-4
• 化学式: C₁₃H₁₅ClSe
• 分子量: 285.675
• InChiKey: HWLZCFLBNBSXNP-LFSVMHDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  降冰片烯 、 N,N-diethylbenzeneselenamide 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以82%的产率得到endo-3-chloro-exo-2-phenylselenobicyclo<2.2.1>heptane
  参考文献：
  名称：

  Reactions of areneselenenamides with alkenes in the presence of phosphorus(V) and sulfur(IV) oxyhalides. New synthesis of β-haloalkyl selenides

  摘要：

  A new procedure was proposed for activation of areneselenenamides with phosphorus(V) and sulfur(IV) oxyhalides. According to the (1)H, (13)C, and (31)P NMR data, areneselenenamide reacts with phosphorus oxyhalide to form intermediate adduct in which the phosphorus atom is coordinated at the selenium. Areneselenenamides activated by phosphorus(V) oxyhalides react with alkenes (norbornene and norbornadiene) with high trans-stereoselectivity. Their reactions with terminal olefins are regioselective, and they lead to preferential formation of the corresponding Markovnikov adducts.

  DOI：

  10.1134/s1070428009060062

文献信息

• Phenylselenenyl chloride in acetonitrile-water
  作者：Akio Toshimitsu、Toshiaki Aoai、Hiroto Owada、Sakae Uemura、Masaya Okano

  DOI：10.1016/s0040-4020(01)96781-x

  日期：1985.1

  convenient method for hydroxyselenation of olefins so far reported. When the reaction was applied to conjugated dienes, monohydroxyselenated products were obtained in good to excellent yields. From non-conjugated dienes, on the other hand, cyclic ethers containing two phenylseleno groups were produced in good to excellent yields, the first step of this reaction being the hydroxyselenation of one double bond

  苯硒基氯与烯烃在乙腈水溶液中的反应以优异的收率提供了β-羟烷基苯基硒化物，为迄今为止报道的烯烃的羟基硒化提供了最方便的方法。当将反应应用于共轭二烯时，以良好至优异的产率获得了单羟基硒化的产物。另一方面，由非共轭二烯以良好至极佳的产率制备了含有两个苯基硒烯基的环状醚，该反应的第一步是一个双键的羟基硒基化。
• Garratt, Dennis G.; Kabo, Ann, Canadian Journal of Chemistry, 1980, vol. 58, p. 1030 - 1041
  作者：Garratt, Dennis G.、Kabo, Ann

  DOI：——

  日期：——
• Beaulieu, Pierre L.; Morisset, Veronique M.; Garratt, Dennis G., Canadian Journal of Chemistry, 1980, vol. 58, p. 1005 - 1013
  作者：Beaulieu, Pierre L.、Morisset, Veronique M.、Garratt, Dennis G.

  DOI：——

  日期：——