1-(iodomethyl)indane | 107657-96-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-(iodomethyl)indane
• 英文别名: 1-iodomethylindan；1-(iodomethyl)-2,3-dihydro-1H-indene
• CAS: 107657-96-5
• 化学式: C₁₀H₁₁I
• 分子量: 258.102
• InChiKey: WBIGTACZROALII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-(丁-3-烯-1-基)苯胺 在 盐酸 、 hexafluorophosphoric acid 、 sodium iodide 、 sodium nitrite 作用下， 以 丙酮 为溶剂， 反应 0.25h， 生成 1-(iodomethyl)indane
  参考文献：
  名称：

  Iododediazoniation of arenediazonium salts accompanied by aryl radical ring closure

  摘要：

  DOI：

  10.1021/jo00386a007

文献信息

• Catalytic Cycloisomerization of Unsaturated Organoiodides
  作者：William F. Bailey、Matthew W. Carson

  DOI：10.1021/jo981991q

  日期：1998.12.1

  Catalytic quantities of phenyllithium (PhLi) have been found to initiate novel 5-exo cycloisomerization of a variety of structurally diverse unsaturated organoiodides. The isomerization reaction appears to be a process of broad synthetic utility for the preparation of iodomethyl-substituted five-membered rings. Primary, secondary, tertiary, or aryl iodides tethered to a suitably positioned carbon-carbon pi-bond are converted cleanly to their cyclic isomers in good to excellent yield (i.e., 70-90%) by simply allowing a hydrocarbon-MTBE solution of the iodide to stand in the presence of a small quantity of PhLi at an appropriate temperature. The mechanism of the cycloisomerization was found to be substrate dependent: unsaturated aryl and primary alkyl iodides undergo isomerization via a three-step cascade (eqs 1-3) mediated by two reversible lithium-iodine exchange reactions bracketing an irreversible 5-exo cyclization of an unsaturated organolithium; unsaturated secondary and tertiary alkyl iodides apparently isomerize via a radical-mediated atom transfer process initiated by homolytic fragmentation of the ate-complex generated upon attack of PhLi on the iodine atom of the substrate.
• BECKWITH A. L. J.; MEIJS G. F., J. ORG. CHEM., 52,(1987) N 10, 1922-1930
  作者：BECKWITH A. L. J.、 MEIJS G. F.

  DOI：——

  日期：——
• Iododediazoniation of arenediazonium salts accompanied by aryl radical ring closure
  作者：Athelstan L. J. Beckwith、Gordon F. Meijs

  DOI：10.1021/jo00386a007

  日期：1987.5