Ethyl 66a-hydroxy-12a,45,55a,60a-tetramethyl-10a,17,40a,47-tetraoxadecacyclo[145.2.2.27,10.213,16.243,46.273,76.281,84.2111,114.2141,144.12,6]hexahexacontahecta-1(49a),2(66a),3,5,7(65a),8,10(64a),11a(12a),13(63a),13a(14a),14,16(62a),41a(42a),43(61a),43a(44a),44,46(60a),47a(48a),50a(51a),52a(53a),54a(55a),56a(57a),58a(76),59a(73),74,81,83-heptacosaen-11,15a(16a),41,45a(46a),71,77,79,85-octayne-4-carboxylate | 499138-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Ethyl 66a-hydroxy-12a,45,55a,60a-tetramethyl-10a,17,40a,47-tetraoxadecacyclo[145.2.2.27,10.213,16.243,46.273,76.281,84.2111,114.2141,144.12,6]hexahexacontahecta-1(49a),2(66a),3,5,7(65a),8,10(64a),11a(12a),13(63a),13a(14a),14,16(62a),41a(42a),43(61a),43a(44a),44,46(60a),47a(48a),50a(51a),52a(53a),54a(55a),56a(57a),58a(76),59a(73),74,81,83-heptacosaen-11,15a(16a),41,45a(46a),71,77,79,85-octayne-4-carboxylate
• CAS: 499138-80-6
• 化学式: C₁₆₉H₂₃₂O₇
• 分子量: 2375.7
• InChiKey: DXEKYTSNSIEZPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  64.3
• 重原子数：
  176
• 可旋转键数：
  115
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  光气 、 Ethyl 66a-hydroxy-12a,45,55a,60a-tetramethyl-10a,17,40a,47-tetraoxadecacyclo[145.2.2.27,10.213,16.243,46.273,76.281,84.2111,114.2141,144.12,6]hexahexacontahecta-1(49a),2(66a),3,5,7(65a),8,10(64a),11a(12a),13(63a),13a(14a),14,16(62a),41a(42a),43(61a),43a(44a),44,46(60a),47a(48a),50a(51a),52a(53a),54a(55a),56a(57a),58a(76),59a(73),74,81,83-heptacosaen-11,15a(16a),41,45a(46a),71,77,79,85-octayne-4-carboxylate 在 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到Ethyl 66a-carbonochloridoyloxy-12a,45,55a,60a-tetramethyl-10a,17,40a,47-tetraoxadecacyclo[145.2.2.27,10.213,16.243,46.273,76.281,84.2111,114.2141,144.12,6]hexahexacontahecta-1(49a),2(66a),3,5,7(65a),8,10(64a),11a(12a),13(63a),13a(14a),14,16(62a),41a(42a),43(61a),43a(44a),44,46(60a),47a(48a),50a(51a),52a(53a),54a(55a),56a(57a),58a(76),59a(73),74,81,83-heptacosaen-11,15a(16a),41,45a(46a),71,77,79,85-octayne-4-carboxylate
  参考文献：
  名称：

  环大小对链烷合成的影响

  摘要：

  具有87元环的[2]邻烷的合成得到改进，并扩展到具有63元和147元环的[2]邻苯二甲。关键特征之一是苯酚之间在2位和6位上具有甲苯取代基的碳酸酯键合，可作为大环和环前体的几何排列的共价模板。螺纹环前体的随后环化产生了以主链烷烃为主要产物，并通过碳酸盐水解将其转化为链烷烃。除环戊烷外，其哑铃状异构体也在环化步骤中形成。根据已知的模板碳酸盐部分的构象以及环烷和哑铃比例对环大小的强烈依赖性，哑铃' 其起源归因于大环的构象柔韧性，而不是归因于碳酸盐部分的几何歧义。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2003）

  DOI：

  10.1002/ejoc.200300232
• 作为产物：
  描述：

  ethyl 3,5-bis-{4-[25-(3,5-dimethyl-4-(25-(4-ethynylphenyl)pentacos-24-yn-1-yloxy)phenyl)pentacos-24-yn-1-yloxy]phenyl}-4-hydroxybenzoate 在 copper(l) chloride 、 copper dichloride 作用下， 以 吡啶 、 邻二氯苯 为溶剂， 反应 72.0h， 以80%的产率得到Ethyl 66a-hydroxy-12a,45,55a,60a-tetramethyl-10a,17,40a,47-tetraoxadecacyclo[145.2.2.27,10.213,16.243,46.273,76.281,84.2111,114.2141,144.12,6]hexahexacontahecta-1(49a),2(66a),3,5,7(65a),8,10(64a),11a(12a),13(63a),13a(14a),14,16(62a),41a(42a),43(61a),43a(44a),44,46(60a),47a(48a),50a(51a),52a(53a),54a(55a),56a(57a),58a(76),59a(73),74,81,83-heptacosaen-11,15a(16a),41,45a(46a),71,77,79,85-octayne-4-carboxylate
  参考文献：
  名称：

  An Efficient Synthesis of Liquid Crystalline Gigantocycles Combining Banana-Shaped and Rod-Like Mesogenic Units

  摘要：

  The synthesis of monodisperse gigantocycles with 63, 87, and 147 ring atoms on the gram scale is described. These molecules were assembled from terphenylene derivatives and long, flexible chains which were mainly aliphatic, with I terminal alkyne groups. The latter allowed for ring formation through oxidative alkyne dimerization in high yield (80-87%). The combination of a rod-like and a banana-shaped mesogen connected by flexible chains within the backbone of a ring gives rise to nematic and smectic mesophases.

  DOI：

  10.1002/1521-3765(20021115)8:22<5094::aid-chem5094>3.0.co;2-6

文献信息

• An Efficient Synthesis of Liquid Crystalline Gigantocycles Combining Banana-Shaped and Rod-Like Mesogenic Units
  作者：Adelheid Godt、Stefan Duda、Ömer Ünsal、Jürgen Thiel、Alice Härter、Mark Roos、Carsten Tschierske、Siegmar Diele

  DOI：10.1002/1521-3765(20021115)8:22<5094::aid-chem5094>3.0.co;2-6

  日期：2002.11.15

  The synthesis of monodisperse gigantocycles with 63, 87, and 147 ring atoms on the gram scale is described. These molecules were assembled from terphenylene derivatives and long, flexible chains which were mainly aliphatic, with I terminal alkyne groups. The latter allowed for ring formation through oxidative alkyne dimerization in high yield (80-87%). The combination of a rod-like and a banana-shaped mesogen connected by flexible chains within the backbone of a ring gives rise to nematic and smectic mesophases.
• The Effect of Ring Size on Catenane Synthesis
  作者：Stefan Duda、Adelheid Godt

  DOI：10.1002/ejoc.200300232

  日期：2003.9

  The synthesis of a [2]catenane with 87-membered rings was improved and extended to [2]catenanes with 63- and 147-membered rings. One of the key features is the carbonate linkage between phenols with tolane substituents in the 2- and 6-positions, which serves as a covalent template for the geometrical arrangement of a macrocycle and a ring precursor. Subsequent cyclization of the threaded ring precursor

  具有87元环的[2]邻烷的合成得到改进，并扩展到具有63元和147元环的[2]邻苯二甲。关键特征之一是苯酚之间在2位和6位上具有甲苯取代基的碳酸酯键合，可作为大环和环前体的几何排列的共价模板。螺纹环前体的随后环化产生了以主链烷烃为主要产物，并通过碳酸盐水解将其转化为链烷烃。除环戊烷外，其哑铃状异构体也在环化步骤中形成。根据已知的模板碳酸盐部分的构象以及环烷和哑铃比例对环大小的强烈依赖性，哑铃' 其起源归因于大环的构象柔韧性，而不是归因于碳酸盐部分的几何歧义。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2003）