Heptacyclo[37.3.1.14,8.111,15.118,22.125,29.132,36]octatetraconta-1(43),4(48),5,7,11(47),12,14,18(46),19,21,25,27,29(45),32,34,36(44),39,41-octadecaen-2,9,16,23,30,37-hexayne-6,13,20,27,34,41-hexol | 152266-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Heptacyclo[37.3.1.14,8.111,15.118,22.125,29.132,36]octatetraconta-1(43),4(48),5,7,11(47),12,14,18(46),19,21,25,27,29(45),32,34,36(44),39,41-octadecaen-2,9,16,23,30,37-hexayne-6,13,20,27,34,41-hexol
• 英文别名: heptacyclo[37.3.1.14,8.111,15.118,22.125,29.132,36]octatetraconta-1(43),4(48),5,7,11(47),12,14,18(46),19,21,25,27,29(45),32,34,36(44),39,41-octadecaen-2,9,16,23,30,37-hexayne-6,13,20,27,34,41-hexol
• CAS: 152266-41-6
• 化学式: C₄₈H₂₄O₆
• 分子量: 696.715
• InChiKey: RBSUNNDVNWECOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  54
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  壬酸 、 Heptacyclo[37.3.1.14,8.111,15.118,22.125,29.132,36]octatetraconta-1(43),4(48),5,7,11(47),12,14,18(46),19,21,25,27,29(45),32,34,36(44),39,41-octadecaen-2,9,16,23,30,37-hexayne-6,13,20,27,34,41-hexol 在 N,N'-二环己基碳二亚胺 、 DPTS 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Geometrically-Controlled and Site-Specifically-Functionalized Phenylacetylene Macrocycles

  摘要：

  A convergent, stepwise synthesis of linear phenylacetylene sequences (PASs) is described. The methodology allows for complete control over chain length, sequence order of monomers, and functional group placement. Chain growth follows geometric progression thus allowing sequences of length 2(n), where n is the number of repetitive cycles, to be assembled in a total of just 3.n steps (two deprotections and one coupling for each cycle). Sequences of length other than 2(n) as well as sequences having a particular arrangement of co-monomer units, can also be realized by merging parallel repetitive cycles. Upon deprotection of the termini, these PASs can be cyclized to phenylacetylene macrocycles (PAMs) in high yield. Control over the ring structure of PAMs is determined by the chemistry of precursor PASs; the size of the macrocycle is related to the sequence length, while the geometry of the macrocycle and the position of the pendant functional groups on the macrocycle is governed by co-monomer sequence order. PAMs with four, five, six, seven, and twelve phenylacetylene monomer units, as well as a variety of site-specifically-functionalized PAMs, have been synthesized with this method. Finally, functional group transformations have been performed on some of the PAMs which lead to PAMs with new functionality. The versatile and efficient approach to this family of geometrically well-defined macrocycles offers potential for producing st set of modular building blocks to rationally assemble molecular crystals and liquid crystals. For this reason, the solid-state characteristics of the hydrocarbon skeletons are of interest. In spite of their solubility in common solvents, hydrocarbon PAMs are shown to yield crystals with remarkable thermal stability and high melting points. Three PAM hydrocarbons are shown not to exhibit melting transitions up to ca 400 degrees C, at which point an abrupt thermal irreversible reaction occurs, apparently involving a solid-state polymerization of the acetylene units.

  DOI：

  10.1021/ja00089a012
• 作为产物：
  描述：

  在 copper(l) iodide 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲醇 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 13.0h， 生成 Heptacyclo[37.3.1.14,8.111,15.118,22.125,29.132,36]octatetraconta-1(43),4(48),5,7,11(47),12,14,18(46),19,21,25,27,29(45),32,34,36(44),39,41-octadecaen-2,9,16,23,30,37-hexayne-6,13,20,27,34,41-hexol
  参考文献：
  名称：

  Geometrically-Controlled and Site-Specifically-Functionalized Phenylacetylene Macrocycles

  摘要：

  A convergent, stepwise synthesis of linear phenylacetylene sequences (PASs) is described. The methodology allows for complete control over chain length, sequence order of monomers, and functional group placement. Chain growth follows geometric progression thus allowing sequences of length 2(n), where n is the number of repetitive cycles, to be assembled in a total of just 3.n steps (two deprotections and one coupling for each cycle). Sequences of length other than 2(n) as well as sequences having a particular arrangement of co-monomer units, can also be realized by merging parallel repetitive cycles. Upon deprotection of the termini, these PASs can be cyclized to phenylacetylene macrocycles (PAMs) in high yield. Control over the ring structure of PAMs is determined by the chemistry of precursor PASs; the size of the macrocycle is related to the sequence length, while the geometry of the macrocycle and the position of the pendant functional groups on the macrocycle is governed by co-monomer sequence order. PAMs with four, five, six, seven, and twelve phenylacetylene monomer units, as well as a variety of site-specifically-functionalized PAMs, have been synthesized with this method. Finally, functional group transformations have been performed on some of the PAMs which lead to PAMs with new functionality. The versatile and efficient approach to this family of geometrically well-defined macrocycles offers potential for producing st set of modular building blocks to rationally assemble molecular crystals and liquid crystals. For this reason, the solid-state characteristics of the hydrocarbon skeletons are of interest. In spite of their solubility in common solvents, hydrocarbon PAMs are shown to yield crystals with remarkable thermal stability and high melting points. Three PAM hydrocarbons are shown not to exhibit melting transitions up to ca 400 degrees C, at which point an abrupt thermal irreversible reaction occurs, apparently involving a solid-state polymerization of the acetylene units.

  DOI：

  10.1021/ja00089a012

文献信息

• Geometrically-Controlled and Site-Specifically-Functionalized Phenylacetylene Macrocycles
  作者：Jinshan Zhang、Douglas J. Pesak、James L. Ludwick、Jeffrey S. Moore

  DOI：10.1021/ja00089a012

  日期：1994.5

  A convergent, stepwise synthesis of linear phenylacetylene sequences (PASs) is described. The methodology allows for complete control over chain length, sequence order of monomers, and functional group placement. Chain growth follows geometric progression thus allowing sequences of length 2(n), where n is the number of repetitive cycles, to be assembled in a total of just 3.n steps (two deprotections and one coupling for each cycle). Sequences of length other than 2(n) as well as sequences having a particular arrangement of co-monomer units, can also be realized by merging parallel repetitive cycles. Upon deprotection of the termini, these PASs can be cyclized to phenylacetylene macrocycles (PAMs) in high yield. Control over the ring structure of PAMs is determined by the chemistry of precursor PASs; the size of the macrocycle is related to the sequence length, while the geometry of the macrocycle and the position of the pendant functional groups on the macrocycle is governed by co-monomer sequence order. PAMs with four, five, six, seven, and twelve phenylacetylene monomer units, as well as a variety of site-specifically-functionalized PAMs, have been synthesized with this method. Finally, functional group transformations have been performed on some of the PAMs which lead to PAMs with new functionality. The versatile and efficient approach to this family of geometrically well-defined macrocycles offers potential for producing st set of modular building blocks to rationally assemble molecular crystals and liquid crystals. For this reason, the solid-state characteristics of the hydrocarbon skeletons are of interest. In spite of their solubility in common solvents, hydrocarbon PAMs are shown to yield crystals with remarkable thermal stability and high melting points. Three PAM hydrocarbons are shown not to exhibit melting transitions up to ca 400 degrees C, at which point an abrupt thermal irreversible reaction occurs, apparently involving a solid-state polymerization of the acetylene units.