Triptindan-9-one | 134939-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: Triptindan-9-one
• 英文别名: 9-triptindanone；hexacyclo[7.7.7.01,9.02,7.011,16.017,22]tricosa-2,4,6,11,13,15,17,19,21-nonaen-8-one
• CAS: 134939-91-6
• 化学式: C₂₃H₁₆O
• 分子量: 308.379
• InChiKey: AFNAEHUQAYNMDU-UHFFFAOYSA-N

物化性质

• 熔点：
  183 °C(Solv: methanol (67-56-1))
• 沸点：
  471.6±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Triptindan-9-one 在 disodium hydrogenphosphate 、 potassium dihydrogenphosphate 、 水 、 溴 、 silica gel 、 sodium bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 10.5h， 生成 9,10,11-triptindanetrione
  参考文献：
  名称：

  Benzoannulated centropolyquinones. 8. Synthesis and reactions of 9,10,11-triptindantrione and some other functionalized tribenzo[3.3.3]propellanes (9H,10H-4b,9a-([1,2]benzenomethano)indeno[1,2-a]indenes)

  摘要：

  A new and efficient route to the tribenzo[3.3.3]propellane 1 (triptindan) and to some interesting derivatives such as 9-triptindanone (13) and 9,10,11-triptindantrione (3) has been developed. The propellane framework of 13 is accessible from 1,3-indandione in only two steps. Triketone 3, a versatile substrate with formal C3-upsilon molecular symmetry, is obtained from 13 in two further steps. First examples are presented for reactions of 3 leading to more complex benzoannelated centropolyquinanes (centropolyindans).

  DOI：

  10.1021/jo00015a034
• 作为产物：
  描述：

  2,2-dibenzyl-2,3-dihydro-1H-indene-1,3-dione 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 以91%的产率得到Triptindan-9-one
  参考文献：
  名称：

  Benzoannulated centropolyquinones. 8. Synthesis and reactions of 9,10,11-triptindantrione and some other functionalized tribenzo[3.3.3]propellanes (9H,10H-4b,9a-([1,2]benzenomethano)indeno[1,2-a]indenes)

  摘要：

  A new and efficient route to the tribenzo[3.3.3]propellane 1 (triptindan) and to some interesting derivatives such as 9-triptindanone (13) and 9,10,11-triptindantrione (3) has been developed. The propellane framework of 13 is accessible from 1,3-indandione in only two steps. Triketone 3, a versatile substrate with formal C3-upsilon molecular symmetry, is obtained from 13 in two further steps. First examples are presented for reactions of 3 leading to more complex benzoannelated centropolyquinanes (centropolyindans).

  DOI：

  10.1021/jo00015a034

文献信息

• Oxyfunctionalization of Nonnatural Targets by Dioxiranes. Selective Oxidation of Centropolyindans
  作者：Dietmar Kuck、Andreas Schuster、Caterina Fusco、Michele Fiorentino、Ruggero Curci

  DOI：10.1021/ja00085a017

  日期：1994.3

  and selectivity of the dioxiranes with respect to O-insertion into benzhydrylic vs benzylic C-H bonds; for instance in the oxyfunctionalization of the angular centrotriindan 3, the secondary benzylic alcohol 12 and the corresponding ketone 10 are obtained, along with the isomeric tertiary alcohol 11. The potentiality of 1b in effecting multiple oxygen insertion into C-H bonds under quite mild conditions

  四种中心聚茚满（triptindan (2), 1,1'-(o-phenylene)-2,2'-spirobiindan (3), 10-methyltribenzoquinacene (4), and fenestrindan (5)）在苄基和已经使用二甲基二环氧乙烷 1a 和甲基（三氟甲基）二环氧乙烷 1b 实现了刚性多环骨架的 / 或二苯甲基 CH 键。发现后一种试剂比 1a 有效得多，可以使所检查的底物部分和完全氧化官能化。多环骨架的刚性和 2-5 中的空间因子似乎缓和了双环氧乙烷在 O 插入二苯甲基与苄基 CH 键方面的反应性和选择性；例如在有角的中心三茚3的氧官能化中，得到仲苯甲醇12和相应的酮10，与异构叔醇一起 11. 1b 在相当温和的条件下将多个氧插入 CH 键的潜力通过 fenestrindan (5) 在桥头位置的显着高产率 4 倍羟基化得到证明。结果被解释为二氧杂环己烷基本上协调的
• A cyclopenta[<i>hi</i>]acephenanthrylene bearing two benzoannelated [3.3.3]propellane units: extension of triptindane chemistry
  作者：Thorsten Hackfort、Beate Neumann、Hans-Georg Stammler、Dietmar Kuck

  DOI：10.1139/cjc-2016-0498

  日期：2017.4

  apparently static on the NMR timescale. Photocyclodehydrogenation of 5 via 8 in benzene solution afforded the title hydrocarbon 6, a 1,2,9,10-tetrahydrocyclopenta[hi]acephenanthrylene merged with two triptindane units, in 85% yield. X-ray structure analysis of 6 revealed an essentially planar phenanthrene unit but significant steric repulsion between the pairs of opposite methylene groups of the [3.3.3]propellane

  Triptindan-9-one (2) 的 McMurry 反应是一种三重苯甲环烷化的 Cs 对称 [3.3.3]propellane 酮，得到 trans-9,9'-bitriptindanylidene (5)，一种空间拥挤的二苯乙烯烃，带有两个 E取向的曲汀丹部分，收率良好。5 的光异构化在光稳定的 E:Z 混合物 (55:45) 中生成了相应的顺式二苯乙烯 8，它采用了类似拥挤的 C2 对称构象，在 NMR 时间尺度上显然是静态的。5经由8在苯溶液中的光环化脱氢得到标题烃6，1,2,9,10-四氢环戊二烯并苯并有两个曲替丹单元，产率为85%。6 的 X 射线结构分析揭示了一个基本上平面的菲单元，但 [3.3.3] 推进核的相反亚甲基对之间存在显着的空间排斥，产生 C2 对称构象。2 在改进的 McMurry 条件下（DME 代替 THF 作为溶剂）反应得到饱和二聚体，9,9'-b
• PAISDOR, BERND;KUCK, DIETMAR, J. ORG. CHEM., 56,(1991) N5, C. 4753-4759
  作者：PAISDOR, BERND、KUCK, DIETMAR

  DOI：——

  日期：——
• Benzoannulated centropolyquinones. 8. Synthesis and reactions of 9,10,11-triptindantrione and some other functionalized tribenzo[3.3.3]propellanes (9H,10H-4b,9a-([1,2]benzenomethano)indeno[1,2-a]indenes)
  作者：Bernd Paisdor、Dietmar Kuck

  DOI：10.1021/jo00015a034

  日期：1991.7

  A new and efficient route to the tribenzo[3.3.3]propellane 1 (triptindan) and to some interesting derivatives such as 9-triptindanone (13) and 9,10,11-triptindantrione (3) has been developed. The propellane framework of 13 is accessible from 1,3-indandione in only two steps. Triketone 3, a versatile substrate with formal C3-upsilon molecular symmetry, is obtained from 13 in two further steps. First examples are presented for reactions of 3 leading to more complex benzoannelated centropolyquinanes (centropolyindans).