(Z)-3-iodo-1,2,3-triphenyl-2-propen-1-ol | 163355-73-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-3-iodo-1,2,3-triphenyl-2-propen-1-ol
• 英文别名: (Z)-3-iodo-1,2,3-triphenylprop-2-en-1-ol
• CAS: 163355-73-5
• 化学式: C₂₁H₁₇IO
• 分子量: 412.27
• InChiKey: IJMCNIYFWORRIP-VXPUYCOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-iodo-1,2,3-triphenyl-2-propen-1-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到3-iodo-1,2-diphenyl-1H-indene
  参考文献：
  名称：

  Efficient Synthesis of 3-Iodoindenes via Lewis-Acid Catalyzed Friedel−Crafts Cyclization of Iodinated Allylic Alcohols

  摘要：

  A convenient BF3 center dot Et2O-catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols is reported. The present reaction provides an efficient protocol to 3-iodo-1H-indene derivatives in good to high yields under mild conditions. Further, the iodoindene derivatives are valuable synthetic building blocks for elaboration of molecular complexity, such as in the construction of multiaryl substituted indenes by Suzuki coupling reaction.

  DOI：

  10.1021/jo800232p
• 作为产物：
  描述：

  苯甲醛 、 二苯基乙炔 在 二氯二茂锆 、 乙基溴化镁 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (Z)-3-iodo-1,2,3-triphenyl-2-propen-1-ol
  参考文献：
  名称：

  Efficient Synthesis of 3-Iodoindenes via Lewis-Acid Catalyzed Friedel−Crafts Cyclization of Iodinated Allylic Alcohols

  摘要：

  A convenient BF3 center dot Et2O-catalyzed Friedel-Crafts cyclization of iodinated allylic alcohols is reported. The present reaction provides an efficient protocol to 3-iodo-1H-indene derivatives in good to high yields under mild conditions. Further, the iodoindene derivatives are valuable synthetic building blocks for elaboration of molecular complexity, such as in the construction of multiaryl substituted indenes by Suzuki coupling reaction.

  DOI：

  10.1021/jo800232p

文献信息

• Acylpalladation of Internal Alkynes and Palladium-Catalyzed Carbonylation of (Z)-.beta.-Iodoenones and Related Derivatives Producing .gamma.-Lactones and .gamma.-Lactams
  作者：Christophe Coperet、Takumichi Sugihara、Guangzhong Wu、Izumi Shimoyama、Ei-ichi Negishi

  DOI：10.1021/ja00117a011

  日期：1995.3

  The reaction of either an internal alkyne-organic halide mixture or (Z)-beta-iodoenones with CO in the presence of a Pd-phosphine catalyst, e.g., Cl2Pd(PPh(3))2, can give one of the three discrete types of compounds as the major products depending on the substrate structure and the reaction conditions. Those substrates which are convertible to (Z)-gamma-oxo-alpha,beta-unsaturated acylpalladium derivatives lacking delta-H atoms are converted to the corresponding 2-butenolides (13) in the presence of water, which serves as a H donor. Carbon monoxide most likely is the source of two electrons. Either in the absence of water (or any other suitable H source) or in the presence of some factors disfavoring the butenolide formation, the same reaction gives the corresponding dimeric product (16). Even in cases where there is an alpha-H atom in the alpha-substitutent, 1,4-elimination products (11), reported to be the major products in a related Pd-catalyzed reaction of terminal alkyne-aryl iodide mixtures with CO, were not detected. In sharp contrast, those substrates which can give rise to (Z)-gamma-oxo-alpha, beta-unsaturated acylpalladium derivatives containing delta-H atoms give, under comparable reaction conditions, enol lactones (12), i.e., (Z)-3-alkylidene-2-butenolides, contaminated with only very minor amounts of 22 even in cases where an excess (4 equiv) of water was present. The required (Z)-beta-iodoenones can be readily prepared in one pot via ZrCp(2)-promoted cyclization of alkynes with nitriles. The ready availability of the starting compounds and the high Z stereoselectivity make the overall sequence an attractive synthetic route to 12. The courses of the Pd-catalyzed carbonylation reactions of (Z)-beta-iodo-alpha,beta-unsaturated imines 23 closely parallel the reactions of enones and produce the corresponding lactams, i.e., 24 and 25.