1,1-dimethyl-7,8,9,10-tetrachloro-1,2,6,10b-tetrahydro-6,10b-o-benzenoaceanthrylene | 127393-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,1-dimethyl-7,8,9,10-tetrachloro-1,2,6,10b-tetrahydro-6,10b-o-benzenoaceanthrylene
• 英文别名: 7,8,9,10-tetrachloro-1,1-dimethyl-1,2,6,10b-tetrahydro-6,10b-o-benzenoaceanthrylene；11,12,13,14-Tetrachloro-2,2-dimethylhexacyclo[7.6.6.11,4.010,15.016,21.08,22]docosa-4(22),5,7,10(15),11,13,16,18,20-nonaene
• CAS: 127393-72-0
• 化学式: C₂₄H₁₆Cl₄
• 分子量: 446.203
• InChiKey: KMVAKXLAMVUBTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  在 盐酸 、 氢氧化钾 、 溶剂黄146 、 叔丁醇 、 亚硝酸异戊酯 作用下， 以 苯 为溶剂， 生成 1,1-dimethyl-7,8,9,10-tetrachloro-1,2,6,10b-tetrahydro-6,10b-o-benzenoaceanthrylene
  参考文献：
  名称：

  Tanaka, Yasuhiro; Yamamoto, Gaku; Oki, Michinori, Chemistry Letters, 1989, p. 2019 - 2022

  摘要：

  DOI：

文献信息

• Syntheses and Structures of 1,1-Dimethyl-1,2,6,10b-tetrahydro-6,10b-<i>o</i>-benzenoaceanthrylenes: Sterically Congested Triptycenes Carrying Five-Membered Ring
  作者：Shinji Toyota、Masahiko Endo、Mitsuru Teruhi、Yoshiyuki Noda、Michinori Oki、Mikio Yamasaki、Takashi Shibahara

  DOI：10.1246/bcsj.66.2088

  日期：1993.7

  compounds which carry a five-membered ring condensed to the triptycene skeleton were synthesized by the Diels-Alder reaction of 1,1-dimethyl-1,2-dihydroaceanthrylene with a benzyne. The structures of three compounds were determined by X-ray crystallography. The molecules have several abnormal bond lengths and angles in addition to significant deformation of the benzene rings as well as the triptycene

  通过 1,1-二甲基-1,2-二氢乙酰蒽与苄的 Diels-Alder 反应合成了带有稠合到三苯乙烯骨架的五元环的空间压缩的标题化合物。三种化合物的结构通过 X 射线晶体学确定。除了苯环和三苯乙烯骨架的显着变形外，分子还有几个异常的键长和角度，以避免关于 C(1)–C(10b) 和 C(1)–C(2) 键的重叠构象. 7-10 位取代基的影响相当小，但在比较 C(10a)-C(10)-取代基键角时发现了一个有趣的键角变形。对二甲氧基化合物进行分子力学计算，以将计算结构与 X 射线结构进行比较。
• Reactivities of Stable Rotamers. XXXIX. Thermal Decomposition of<b><i>t</i></b>-Butyl 3-Methyl-3-(substituted 9-triptycyl)peroxybutanoate Rotamers
  作者：Michinori Oki、Ichiro Fujino、Daisuke Kawaguchi、Kazumasa Chuda、Yoko Moritaka、Yasunori Yamamoto、Shingo Tsuda、Tadashi Akinaga、Michihiko Aki、Hiroharu Kojima、Nobuhiro Morita、Makoto Sakurai、Shinji Toyota、Yasuhiro Tanaka、Toshihiro Tanuma、Gaku Yamamto

  DOI：10.1246/bcsj.70.457

  日期：1997.2

  The ap and sc rotamers of the title compound, where substituents are 1,4-dimethyl, 1,4-dimethoxy, 1,2,3,4-tetrafluoro, and 1,2,3,4-tetrachloro, were thermolyzed in toluene solutions to examine the effects of interactions between the radical center and the substituent. The rates of thermolyses were affected neither by the substituent nor by the rotameric positions, but the product distributions showed dependence on the substituent. In the ap-forms, the effectively bulkier the substituent at the 1-position, the higher the yields of the 5-membered ring compound. This was attributed to the degree of the tilting of the 9-substituent, which forces the radical center to be pushed into the triptycene skeleton. For the sc-forms, the chloro and the methyl substituents exhibited special effects, the former affording a colligation product between benzyl and 2-(1,2,3,4-tetrachloro-9-triptycyl)-2-methylpropyl radicals and the latter showing a tendency of radical migration to the benzylic position. Comparison of the results of thermolyses of the 1,4-dimethyl peroxyester with those of 2(1H)-thioxo-1-pyridyl 3-(1,4-dimethyl-9-triptycyl)-3-methylbutanoate indicates that, although it is believed that these precursors afford the same 2-(1,4-dimethyl-9-triptycyl)-2-methylpropyl radicals, the product distributions were significantly different from each other. These results were attributed to the stabilizing effects of the sulfur compound on the radical in the solvent cage in the latter.

  在甲苯溶液中对取代基为 1,4-二甲基、1,4-二甲氧基、1,2,3,4-四氟和 1,2,3,4-四氯的标题化合物的 ap 和 sc 转聚体进行热解，以考察自由基中心与取代基之间相互作用的影响。热解速率既不受取代基的影响，也不受转子位置的影响，但产物分布却与取代基有关。在 ap 型化合物中，1 位上的取代基越大，5 元环化合物的产量就越高。这是因为 9-取代基的倾斜程度迫使自由基中心挤入三庚烯骨架。对于 sc 形式，氯和甲基取代基显示出特殊效果，前者在苄基和 2-（1,2,3,4-四氯-9-三辛基）-2-甲基丙基自由基之间产生碰撞产物，后者则显示出自由基向苄基位置迁移的趋势。将 1,4-二甲基过氧化酯的热解结果与 2(1H)-硫酮-1-吡啶基 3-(1,4-二甲基-9-三甲苯基)-3-甲基丁酸酯的热解结果进行比较后发现，虽然认为这些前体产生的 2-(1,4-二甲基-9-三甲苯基)-2-甲基丙基自由基相同，但产物分布却明显不同。这些结果归因于硫化合物对后者溶剂笼中自由基的稳定作用。
• How Do Ethane-Type Molecules Avoid Eclipsing When Forced as Such? The Case of 7,8,9,10-Tetrachloro-1,1-dimethyl-1,2,6,10b-tetrahydro-6,10b-<i>o</i>-benzenoaceanthrylene
  作者：Michinori Oki、Masahiko Endo、Yoshiyuki Noda、Shinji Toyota、Mikio Yamasaki、Takashi Shibahara

  DOI：10.1246/cl.1992.273

  日期：1992.2

  The molecular structure of the title compound was determined by X-ray crystallography. To avoid the eclipsing interactions between the two methyl groups at the 1-position and the triptycene skeleton, the molecule exhibited several unusual bond lengths and bond angles. The benzene rings in the molecule were also deformed from planarity.

  标题化合物的分子结构是通过 X 射线晶体学确定的。为了避免 1 位上的两个甲基与三庚烯骨架之间的黯然作用，分子呈现出几种不同寻常的键长和键角。分子中的苯环也发生了平面变形。
• Reactivities of Stable Rotamers. XLIII. Diazotization of 2-Methyl-2-(1,2,3,4-tetrachloro- and 1,4-dimethoxy-9-triptycyl)propylamine Rotamers
  作者：Michinori Oki、Satoshi Yoshida、Yasushi Taguchi、Ichiro Minato、Koji Nobuoka、Norihiro Fukada、Shinji Toyota、Toshimasa Tanaka、Yasuhiro Tanaka、Gaku Yamamoto

  DOI：10.1246/bcsj.73.2563

  日期：2000.11

  derived by the attack of the carbocation on an unsubstituted benzeno bridge and esters derived from the acid which was used for diazotization. These two compounds are the products from the cation prior to the rearrangement. The sc-tetrachloro compound afforded the esters of the organic acids as almost an exclusive product and the sc-dimethoxy compound afforded a cyclized compound which is derived from

  标题胺是由相应的羧酸旋转异构体通过叠氮化物和异氰酸酯制备的。这些胺与亚硝酸异戊酯和有机酸的重氮化通常得到烯烃，这些烯烃源自介入阳离子的 Wagner-Meerwein 型重排，然后去质子化。其他产品包括通过碳正离子攻击未取代的苯桥而衍生的环状化合物和衍生自用于重氮化的酸的酯。这两种化合物是重排前阳离子的产物。sc-四氯化合物提供有机酸的酯作为几乎唯一的产物，sc-二甲氧基化合物提供环化化合物，其衍生自 1-甲氧基与阳离子的亲核反应，然后对所得氧鎓离子进行去甲基化。这些特征归因于 1-取代基与中间碳正离子的强相互作用。同意...
• TANAKA, YASUHIRO;YAMAMOTO, GAKU;OKI, MICHINORI, CHEM. LETT.,(1989) N1, C. 2019-2022
  作者：TANAKA, YASUHIRO、YAMAMOTO, GAKU、OKI, MICHINORI

  DOI：——

  日期：——