Benzaldehyde, 3,3'-(2-methylene-1,3-propanediyl)bis[2-hydroxy- | 324541-89-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Benzaldehyde, 3,3'-(2-methylene-1,3-propanediyl)bis[2-hydroxy-
• 英文别名: 3-[2-[(3-formyl-2-hydroxyphenyl)methyl]prop-2-enyl]-2-hydroxybenzaldehyde
• CAS: 324541-89-1
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: YOEPKJJOBXAWMV-UHFFFAOYSA-N

物化性质

• 沸点：
  437.5±45.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  Benzaldehyde, 3,3'-(2-methylene-1,3-propanediyl)bis[2-hydroxy- 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 30.0h， 生成 18,41-Dimethylidene-3,10,26,33-tetrazaheptacyclo[41.3.1.112,16.120,24.135,39.04,9.027,32]pentaconta-1(46),4,6,8,12,14,16(50),20(49),21,23,27,29,31,35,37,39(48),43(47),44-octadecaene-47,48,49,50-tetrol
  参考文献：
  名称：

  Highly selective formation of 2∶2 macrocycles from a novel hydroxybenzaldehyde derivative and diamines

  摘要：

  具有异丁烯基连接的羟基苯甲醛衍生物与多种二胺发生反应，可有效生成 2â¶2大环化合物。

  DOI：

  10.1039/b005536k
• 作为产物：
  描述：

  2,2′-[(2-methylenepropane-1,3-diyl)bis(oxy)]dibenzaldehyde 反应 10.0h， 以79%的产率得到Benzaldehyde, 3,3'-(2-methylene-1,3-propanediyl)bis[2-hydroxy-
  参考文献：
  名称：

  Highly selective formation of 2∶2 macrocycles from a novel hydroxybenzaldehyde derivative and diamines

  摘要：

  具有异丁烯基连接的羟基苯甲醛衍生物与多种二胺发生反应，可有效生成 2â¶2大环化合物。

  DOI：

  10.1039/b005536k

文献信息

• Conformational Study of Isobutenylene Chains in Tandem Claisen Rearrangement Products. Insights from X-ray Crystallography and¹H NMR for Salicylideneaniline Derivatives
  作者：Hirohiko Houjou、Seiji Tsuzuki、Yoshinobu Nagawa、Kazuhisa Hiratani

  DOI：10.1246/bcsj.75.831

  日期：2002.4

  A new variety of salicylideneaniline derivatives were prepared from a substituted aniline and a bis(hydroxybenzaldehyde) which has been synthesized through a tandem Claisen rearrangement reaction. X-ray crystal structures were obtained for many of the products. With respect to the conformation of their isobutenylene chain, the crystal structures can be classified into three groups: i.e., skew–skew

  以取代苯胺和双（羟基苯甲醛）为原料，通过串联克莱森重排反应合成了一系列新的水杨基苯胺衍生物。获得了许多产品的 X 射线晶体结构。就其异丁烯链的构象而言，晶体结构可分为三组：即偏斜(I)、顺-偏(II)和顺-顺(III)构象异构体。这些化合物的 1H NMR 谱有显着差异，尤其是异丁烯部分。外亚甲基 (Ha) 和苄基亚甲基 (Hb) 的一组化学位移 (δ (Ha), δ (Hb)) 是对 NMR 光谱进行分类的良好指标，这些值也反映了在晶体状态下发现的异丁烯链。即，I、II、和 III 分别对应于 (5.10, 3.43)、(4.86, 3.43) 和 (4.74, 3.56) 附近的 (δ (Ha), δ (Hb)) 值 (ppm)。络合研究证实了这一结果......
• Spontaneous helical folding of bis(Ni-salphen) complexes in solution and in the solid state: spectroscopic tracking of the unfolding process induced by Na+ ions
  作者：Hiroto Achira、Muneyuki Ito、Toshiki Mutai、Isao Yoshikawa、Koji Araki、Hirohiko Houjou

  DOI：10.1039/c3dt53397b

  日期：——

  Four kinds of bis(Ni-salphen) complexes containing a 2-methylenepropane-1,3-diyl linker were synthesised and characterised. Crystal structural analysis revealed that one of the complexes folded into a helical structure, in which two Ni atoms were at a distance of 3.2 Å from each other. NMR measurements suggested that a similar folded state was maintained in solution, and the energy barrier for refolding

  合成并表征了四种含有2-亚甲基丙烷-1,3-二基连接基的双（Ni-Salphen）配合物。晶体结构分析表明，其中一个配合物折叠成螺旋结构，其中两个Ni原子彼此之间的距离为3.2。NMR测量表明在溶液中维持相似的折叠状态，并且通过展开状态重新折叠的能垒为47kJ mol -1。折叠的复合物在其UV-Vis吸收结构中也表现出显着的红移。钠离子的添加​​导致络合物的展开，并且相应的光谱归因于实际上是孤立的状态。DFT计算很好地再现了能垒和折叠引起的红移。
• Factors Affecting the Conformational Preference and Magnetic Shielding of Isobutenylene Chains in Macrocyclic Salicylideneaniline Derivatives
  作者：Hirohiko Houjou、Seiji Tsuzuki、Yoshinobu Nagawa、Masatoshi Kanesato、Kazuhisa Hiratani

  DOI：10.1246/bcsj.76.2405

  日期：2003.12

  The 1H NMR chemical shifts and X-ray crystal structures of various salicylideneaniline derivatives containing an isobutenylene (2-methylenepropane-1,3-diyl) chain were analyzed in detail. In solution, these compounds were present to some extent as syn–syn conformers with respect to the isobutenylene chain; the actual syn–syn population depended on the molecular structure, especially on the size of the macrocycle. Small substituents on the phenyl ring hardly affected the stability of the syn–syn form at all, whereas replacement of the phenyl group with a naphthalene moiety considerably destabilized the syn–syn form relative to the syn–skew form. The conformation–chemical shift relationship was validly maintained irrespective of the substituent, provided the conformational preference was correctly taken into account.

  我们详细分析了含有异丁烯（2-亚甲基丙烷-1,3-二基）链的各种水杨酰苯胺衍生物的 1H NMR 化学位移和 X 射线晶体结构。在溶液中，这些化合物在一定程度上以异丁烯链的同步构象存在；实际的同步构象群取决于分子结构，特别是大环的大小。苯基环上的小取代基几乎不会影响同步构象的稳定性，而用萘基取代苯基则会大大降低同步构象相对于同步斜构象的稳定性。只要正确考虑了构象偏好，无论取代基如何，构象-化学位移关系都能得到有效保持。
• The architecture of dinuclear Ni and Cu complexes: twisted and parallel forms controlled by the self-assembly of Schiff base ligands
  作者：Hirohiko Houjou、Atsushi Iwasaki、Tamako Ogihara、Masatoshi Kanesato、Sadatoshi Akabori、Kazuhisa Hiratani

  DOI：10.1039/b212285p

  日期：2003.4.29

  Novel dinuclear complexes were synthesized through the self-assembly of macrocyclic Schiff base ligands and either nickel(II) or copper(II) ions. X-Ray structural analysis revealed that the complexes had either a double helix (twisted) structure in which each atom had a distorted square-planar coordination or a non-helical (parallel) structure in which the metals had octahedral coordination. The helical

  通过大环的自组装合成新型双核配合物 希夫碱 配体并且或者镍（II）或铜（II）离子。X射线结构分析表明，该配合物具有双螺旋（扭曲）结构（其中每个原子具有扭曲的方平面配位）或非螺旋（平行）结构（其中金属具有八面体配位）。螺旋复合物非常不寻常，因为它们的螺旋结构不是起源于协调中心，而是主要起源于螺旋结构中的连接基部分。配体。讨论了影响螺旋结构形成的几个因素。
• Self-assembly of double stranded dinuclear titanium(iv)–Schiff base complexes and formation of intramolecular µ-oxo bridges
  作者：Maddali L.N. Rao、Hirohiko Houjou、Kazuhisa Hiratani

  DOI：10.1039/b106447a

  日期：——

  The reaction of titanium isopropoxide with a Schiff base ligand containing an isobutenyl linker leads to double stranded dinuclear titanium(IV)-Schiff base complexes through self-assembly with concomitant formation of intramolecular mu-oxo bridges upon hydrolysis.

  异丙氧基钛与包含异丁烯基接头的席夫碱配体的反应通过自组装形成双链双核钛（IV）-席夫碱配合物，并在水解时伴随形成分子内的mu-氧代桥。