trans-1-chloro-2-iodo-1,2,3,4-tetrahydronaphthalene | 128856-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: trans-1-chloro-2-iodo-1,2,3,4-tetrahydronaphthalene
• CAS: 128856-89-3
• 化学式: C₁₀H₁₀ClI
• 分子量: 292.547
• InChiKey: BPSFQXNIPOAVRJ-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  trans-1-chloro-2-iodo-1,2,3,4-tetrahydronaphthalene 在 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 以53%的产率得到
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865
• 作为产物：
  描述：

  1,2-二氢萘 在 (2R,5R)-1-iodo-2,5-dimethyltetrahydrothiophenium hexachloroantimonate 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 生成 trans-1-chloro-2-iodo-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865

文献信息

• Regio- and stereospecific iodochlorination of alkenes and alkynes with polystyrene-[4-vinylpridinium dichloroiodate(I)]
  作者：Boris kˇet、Pavel Zupet、Marko Zupan

  DOI：10.1016/s0040-4020(01)82031-7

  日期：1990.1