HMDHP | 20349-16-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: HMDHP
• 英文别名: 1,3,6,8-trans-15,16-hexamethyl-dihydropyren
• CAS: 20349-16-0
• 化学式: C₂₂H₂₄
• 分子量: 288.433
• InChiKey: IOVCATHMUYCWMM-HZCBDIJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  HMDHP 在 lithium aluminium tetrahydride 、 三氯化铝 、 四氯化锡 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 2-Methyl-HMDHP
  参考文献：
  名称：

  Synthesis and chemistry of hexamethyl-trans-15,16-dihydropyrene

  摘要：

  DOI：

  10.1021/jo00985a001
• 作为产物：
  描述：

  1,3,6,8,10b,10c-Hexamethyl-2,7,10b,10c-tetrahydro-pyrene 在 palladium on activated charcoal 作用下， 以 甲苯 为溶剂， 生成 HMDHP
  参考文献：
  名称：

  Synthesis and chemistry of hexamethyl-trans-15,16-dihydropyrene

  摘要：

  DOI：

  10.1021/jo00985a001

文献信息

• Synthesis, Reactions, and Structural and NMR Features of [2.2]Metacyclophane Monoenes and Their Tricarbonylchromium and Cyclopentadienyliron(+) Complexes
  作者：Reginald H. Mitchell、Limin Zhang

  DOI：10.1021/jo990721k

  日期：1999.9.1

  8,16-Dimethyl-, 5,8,13,16-tetramethyl, and 4,6,8,12,14,16-hexamethyl[2,2]metacyclophanene have been synthesized from the corresponding methyl-substituted 3-thia[3.2]metacyclophane precursors via a Wittig rearrangement-Hofmann elimination procedure. Simple addition of bromine or similar electrophiles to the bridge double bond of the cyclophane monoenes did not occur; rather, the methyl-substituted dihydropyrenes were formed. However, mono- and bis-tricarbonylchromium and monocyclopentadienyliron complexes were obtained using ligand-exchange reactions. Addition of bromine to the cyclophane bridge double bond of the iron complex did occur, but unusually slowly. Surprisingly, debromination rather than dehydrobromination occurred when the dibromo addition product was treated with a variety of bases. Photoisomerization of the monoenes and nucleophilic substitution of the metal complexes was also investigated. The geometries of the monoenes and their complexes were compared to the cyclophanes and the cyclophanedienes and to the monothia- and dithiacyclophanes, by comparison of X-ray and calculated structural data and NMR spectroscopic data. Introduction of double bonds into the cyclophane bridges causes the cyclophane step to be less steep but increases distortion of the internal atoms out of the plane of the benzene rings. Making the bridges nonidentical also causes a sideways twist of the step.