1-iodo-4-phenylcubane | 124225-33-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-iodo-4-phenylcubane
• 英文别名: 4-phenylcubyl iodide；4-phenyliodocubane
• CAS: 124225-33-8
• 化学式: C₁₄H₁₁I
• 分子量: 306.146
• InChiKey: GJTUWJUJDGKSOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-iodo-4-phenylcubane 在 甲醇 、 叔丁基锂 作用下， 生成 phenylcubane
  参考文献：
  名称：

  Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)¹

  摘要：

  On treatment with an organolithium 1,4-diiodocubane generates cubane-1,4-diyl, a highly reactive species, shown here to be a versatile precursor to numerous aryl substituted cubanes, available now for the first time in high yield. The diyl is demonstrated to provide a good route to bicubyl and its derivatives. A kind of "living polymerization" of the diyl is developed to give the p-[n]cubyls. These oligomers are rigid rods made up of cubanes linked together at the 1 and 4 positions, each cubane adding similar to 4.15 Angstrom to the length. The properties of these rods, some more than 15 Angstrom long, are discussed, as are methods for modifying their solubility. X-ray crystallographic analyses of some of these compounds an presented, with emphasis on packing parameters.

  DOI：

  10.1021/ja983441f
• 作为产物：
  描述：

  4-phenylcubanecarboxylic acid chloride 在 4-二甲氨基吡啶 、 2-碘-1,1,1-三氟乙烷 、 2-mercaptopyridine-1-oxide sodium salt 作用下， 以 苯 为溶剂， 反应 0.67h， 以76%的产率得到1-iodo-4-phenylcubane
  参考文献：
  名称：

  古巴的均裂反应。cubyl 和 cubylcarbinyl 自由基的生成和表征

  摘要：

  通过从 1-bromo-4-取代的立方烷中提取溴原子，产生了一系列 4-取代的立方自由基。EPR 观察表明，cubyl 自由基从三乙基硅烷的乙基中提取二级氢原子，主要通过二级组合反应衰变。在-90 o C 时，叔丁氧基从立方烷中提取氢原子的速度至少比环丙烷快26 倍。立方烷上的吸电子取代基大大降低了这一速度。叔丁氧基自由基选择性地从甲基立方烷中提取笼氢而不是伯甲基氢

  DOI：

  10.1021/ja00053a008

文献信息

• Cubanes in Medicinal Chemistry: Synthesis of Functionalized Building Blocks
  作者：Joanna Wlochal、Robert D. M. Davies、Jonathan Burton

  DOI：10.1021/ol501750k

  日期：2014.8.15

  cubane-1,4-dimethylester. A range of synthetic methods have been applied to prepare these cubane building blocks with one or two functional handles to allow easy incorporation into existing medicinal chemistry programs.

  从可商购的古巴-1,4-二甲基酯制备了一系列新的，药学上相关的含古巴分子。已经应用了多种合成方法来制备具有一个或两个功能手柄的这些古巴构建基块，以使其易于并入现有的药物化学程序中。
• 4-Substituted Cubylcarbinylamines:  A New Class of Mechanism-Based Monoamine Oxidase B Inactivators
  作者：Joseph J. P. Zhou、Jianchang Li、Suhbash Upadhyaya、Philip E. Eaton、Richard B. Silverman

  DOI：10.1021/jm9606249

  日期：1997.3.1

  time-dependent, irreversible inactivators of monoamine oxidase B (MAO B). Substrate protects the enzyme from inactivation, but beta-mercaptoethanol does not, suggesting that these compounds are mechanism-based inactivators. All three compounds were also substrates for MAO B with partition ratios ranging from 152 to 536. The 4-substituted analogues were more potent inactivators than the unsubstituted analogue

  合成了苄基羰基胺（1a），（4-环丙基cubyl）羰基胺（1b）和（4-苯基cubyl）羰基胺（1c），它们是时间依赖性的单胺氧化酶B（MAO B）不可逆的灭活剂。底物可保护酶免于灭活，但β-巯基乙醇则不能，表明这些化合物是基于机理的灭活剂。所有这三种化合物也是MAO B的底物，分配比范围为152至536。4-取代的类似物比未取代的类似物更有效的灭活剂，表明在这类灭活剂中有利于4-取代。
• The reactions of 1,4-dihalocubanes with organolithiums. The case for 1,4-cubadiyl
  作者：Philip E. Eaton、John Tsanaktsidis

  DOI：10.1021/ja00158a063

  日期：1990.1

  La lithiation suivie par une carbomethoxylation de dihalogeno-1,4 cubane fournit des derives de cubanecarboxylate-1, cubanedicarboxylate-1,4, de dicubyle-1,4' carboxylate-1, dicubyle-1,4' dicarboxylate-1,4 de methyle ou dimethyle

  La lithiation suvie par une carbomethoxylation de dihalogeno-1,4 cubane Fournit des甲基或二甲基
• Synthesis of alkynylcyclooctatetraenes and alkynylcubanes
  作者：Philip E. Eaton、Daniel Stossel

  DOI：10.1021/jo00017a028

  日期：1991.8

  The couplings of a variety of iodocubanes with terminal acetylenes in refluxing NEt3 in the presence of Cu(I) and Pd(0) were examined. The products, isolated in about 50% yield, were not alkynylcubanes but were instead the first examples of alkynyl-1,3,5,7-cyclooctatetraenes. The first examples of alkynylcubanes (cubylacetylenes) were themselves synthesized in modest yield by Negishi's procedure from alkyl cubyl ketones. Cubylacetylenes were shown to be stable under Heck-like coupling conditions and potentially useful thereby for the introduction of the cubylacetylene moiety into complex systems.
• Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, <i>p</i>-[<i>n</i>]Cubyls, and Cubane-Separated Bis(arenes)¹
  作者：Philip E. Eaton、Kakumanu Pramod、Todd Emrick、Richard Gilardi

  DOI：10.1021/ja983441f

  日期：1999.5.1

  On treatment with an organolithium 1,4-diiodocubane generates cubane-1,4-diyl, a highly reactive species, shown here to be a versatile precursor to numerous aryl substituted cubanes, available now for the first time in high yield. The diyl is demonstrated to provide a good route to bicubyl and its derivatives. A kind of "living polymerization" of the diyl is developed to give the p-[n]cubyls. These oligomers are rigid rods made up of cubanes linked together at the 1 and 4 positions, each cubane adding similar to 4.15 Angstrom to the length. The properties of these rods, some more than 15 Angstrom long, are discussed, as are methods for modifying their solubility. X-ray crystallographic analyses of some of these compounds an presented, with emphasis on packing parameters.