hexahelicene-2,15-dicarboxylic acid | 204138-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: hexahelicene-2,15-dicarboxylic acid
• CAS: 204138-48-7
• 化学式: C₂₈H₁₆O₄
• 分子量: 416.433
• InChiKey: VXROOEYOGOFSDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hexahelicene-2,15-dicarboxylic acid 在 氯化亚砜 作用下， 反应 12.0h， 以90%的产率得到Hexahelicene-2,15-dicarbonyl chloride
  参考文献：
  名称：

  Synthesis of Conjugated Helical Acetylene-Bridged Polymers and Cyclophanes

  摘要：

  Pd(0)-catalyzed reactions of 2,15-diethynyl[6]helicene with derivatives of p- and o-diiodobenzene give, respectively, polymers 4 and cyclophanes 5, in which helicenes are linked by diethynylbenzenes. Both are very soluble in many common solvents. The molar rotation of polymer 4 is greater than that of monomeric analogue 12, and peaks in its UV and CD spectra at wavelengths greater than 350 nm are shifted to the red of those in 12. Cyclophane 5a, which contains two helicene rings, could be isolated from the reaction mixture in pure form. Its maxima in the UV and CD spectra are not shifted to the red of those of 12, most likely because the two helicene rings in 5a are twisted with respect to one another.

  DOI：

  10.1021/jo972101u
• 作为产物：
  描述：

  bis(2-methylpropyl) hexahelicene-2,15-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以15%的产率得到hexahelicene-2,15-dicarboxylic acid
  参考文献：
  名称：

  新的功能性六螺旋 - 六螺旋的合成、手性特性、X 射线晶体结构和比较数据库分析

  摘要：

  已经合成了七个含有不同官能团取代基的新六螺旋烯 (3-7, 9, 10)，并在三种情况下 (4, 8, 10) 进行了光学拆分。测量旋光度并报告CD光谱。已经确定了螺旋 1、3、4、8 和 9 的 X 射线晶体结构，其中 4 表示与丙酮的 1:1 包合物。这些显示了填料中 C−H···O、C−H···π 和 π···π 超分子相互作用的协同相互作用，主要产生分子堆叠 (1, 3, 4, 8)。对这些和相关晶体结构中的分子尺寸进行统计分析，以确定与宏观现象相关的潜在参数，包括旋光度。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300084

文献信息

• New Functional Hexahelicenes − Synthesis, Chiroptical Properties, X-ray Crystal Structures, and Comparative Data Bank Analysis of Hexahelicenes
  作者：Claudia Wachsmann、Edwin Weber、Mátyás Czugler、Wilhelm Seichter

  DOI：10.1002/ejoc.200300084

  日期：2003.8

  (3−7, 9, 10) containing different functional group substituents have been synthesized and, in three cases (4, 8, 10), optically resolved. Optical rotations were measured and CD spectra are reported. X-ray crystal structures of the helicenes 1, 3, 4, 8, and 9 have been determined, of which 4 represents a 1:1 clathrate with acetone. These show a concerted interplay of C−H···O, C−H···π, and π···π supramolecular

  已经合成了七个含有不同官能团取代基的新六螺旋烯 (3-7, 9, 10)，并在三种情况下 (4, 8, 10) 进行了光学拆分。测量旋光度并报告CD光谱。已经确定了螺旋 1、3、4、8 和 9 的 X 射线晶体结构，其中 4 表示与丙酮的 1:1 包合物。这些显示了填料中 C−H···O、C−H···π 和 π···π 超分子相互作用的协同相互作用，主要产生分子堆叠 (1, 3, 4, 8)。对这些和相关晶体结构中的分子尺寸进行统计分析，以确定与宏观现象相关的潜在参数，包括旋光度。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis of Conjugated Helical Acetylene-Bridged Polymers and Cyclophanes
  作者：Joseph M. Fox、Daniel Lin、Yasuhiro Itagaki、Tsuyoshi Fujita

  DOI：10.1021/jo972101u

  日期：1998.3.1

  Pd(0)-catalyzed reactions of 2,15-diethynyl[6]helicene with derivatives of p- and o-diiodobenzene give, respectively, polymers 4 and cyclophanes 5, in which helicenes are linked by diethynylbenzenes. Both are very soluble in many common solvents. The molar rotation of polymer 4 is greater than that of monomeric analogue 12, and peaks in its UV and CD spectra at wavelengths greater than 350 nm are shifted to the red of those in 12. Cyclophane 5a, which contains two helicene rings, could be isolated from the reaction mixture in pure form. Its maxima in the UV and CD spectra are not shifted to the red of those of 12, most likely because the two helicene rings in 5a are twisted with respect to one another.