5-butyl-2,2-bis(methoxymethyl)indan

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-butyl-2,2-bis(methoxymethyl)indan
• 英文别名: 5-Butyl-2,2-bis(methoxymethyl)-1,3-dihydroindene
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: OMDKNTIYXAMIBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-己炔 、 4,4-bis(methoxymethyl)hepta-1,6-diyne 在 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以81%的产率得到5-butyl-2,2-bis(methoxymethyl)indan
  参考文献：
  名称：

  水中空气中铑（I）/阳离子2,2'-联吡啶催化的α，ω-二炔与炔烃的[2 + 2 + 2]环加成反应

  摘要：

  在空气中于水中完成了[Rh（cod）Cl] 2 /阳离子2,2'-联吡啶基系统催化的[2 + 2 + 2]环化α，ω-二炔与末端和内部炔烃的加成反应的简单方法在60°C下。在20 mol％KOH的存在下，反应在1个当量的α，ω-二炔和3个当量的炔烃下平稳进行1 h或9 h，从而以中等至高收率形成了三取代和四取代的苯衍生物。通过萃取分离出有机产物后，残留的水溶液可再用于进一步的反应，直到其催化活性完全降解。

  DOI：

  10.1016/j.tet.2010.06.088

文献信息

• Iridium Complex-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Monoynes and Monoenes
  作者：Satoko Kezuka、Shigeru Tanaka、Toshihito Ohe、Yoshihiko Nakaya、Ryo Takeuchi

  DOI：10.1021/jo051874c

  日期：2006.1.1

  [Ir(cod)Cl](2)/DPPE was found to be a new catalyst for the cycloaddition of alpha,omega-diynes with monoynes to give polysubstituted benzene derivatives in high yields. Internal monoynes as well as terminal monoynes could be used. The reaction tolerates a broad range of functional groups such as alcohol, amine, alkene, ether, halogen, and nitrile. The reaction of 1,6-octadiyne derivatives with 1-alkynes gives ortho products and meta products. The regioselectivity could be controlled by the choice of ligand. The reaction with DPPE was meta selective, with meta selectivity of up to 82%. The reaction with DPPF was ortho selective, with ortho selectivity of up to 88%. We propose a mechanism to account for this regioselective cycloaddition. [Ir(cod)Cl-2]2/DPPE also catalyzed the cycloaddition of alpha-omega-diynes with 2,5-dihydrofuran to give bicyclic cyclohexadiene derivatives. The reaction with 2,3-dihydrofuran and n-butyl vinyl ether gave benzene derivatives instead of cyclohexadiene derivatives. We also propose a mechanism to account for this novel aromatization that includes cleavage of the C-O bond.
• Rhodium(I)/cationic 2,2′-bipyridyl-catalyzed [2+2+2] cycloaddition of α,ω-diynes with alkynes in water under air
  作者：Yun-Hua Wang、Shao-Hsien Huang、Tze-Chiao Lin、Fu-Yu Tsai

  DOI：10.1016/j.tet.2010.06.088

  日期：2010.8

  simply performed procedure for the [Rh(cod)Cl]2/cationic 2,2′-bipyridyl system-catalyzed [2+2+2] cycloaddition of α,ω-diynes with terminal and internal alkynes was achieved in water under air at 60 °C. The reaction proceeded smoothly with 1 equiv α,ω-diynes and 3 equiv alkynes in the presence of 20 mol % KOH for 1 h or 9 h, resulting in the formation of tri- and tetra-substituted benzene derivatives in

  在空气中于水中完成了[Rh（cod）Cl] 2 /阳离子2,2'-联吡啶基系统催化的[2 + 2 + 2]环化α，ω-二炔与末端和内部炔烃的加成反应的简单方法在60°C下。在20 mol％KOH的存在下，反应在1个当量的α，ω-二炔和3个当量的炔烃下平稳进行1 h或9 h，从而以中等至高收率形成了三取代和四取代的苯衍生物。通过萃取分离出有机产物后，残留的水溶液可再用于进一步的反应，直到其催化活性完全降解。