1,3-bis(propylsulfinyl)propane | 34757-36-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: 1,3-bis(propylsulfinyl)propane
• 英文别名: meso-1,3-bis(n-propylsulfinyl)propane；1,3-bis(n-propylsulfinyl)propane
• CAS: 34757-36-3
• 化学式: C₉H₂₀O₂S₂
• 分子量: 224.389
• InChiKey: SZEIOZHUFSVVJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 1,3-bis(propylsulfinyl)propane 以 乙醇 为溶剂， 以45%的产率得到copper(1,3-bis(n-propylsulfinyl)propane) perchlorate
  参考文献：
  名称：

  Bridging properties of disulfoxide ligands: crystal structure of copper(1,3-bis(n-propylsulfinyl)propane) perchlorate

  摘要：

  The first crystal structure of a copper(II) complex containing a disulfoxide is reported. The 1,3-bis(n-propylsulfinyl)propane ligand acts as a bis(monodentate) ligand bridging the metal ions through its oxygen atoms to form layers of distorted square planar CuO4 groups (Cu-O, 1.942(3) Angstrom) connected by (PrS)-Pr-n(CH2)(3)(SPr)-Pr-n bridges (S-O, 1.533(5) Angstrom), with homochiral sulfur atoms. Each copper atom achieves a square pyramidal coordination, interacting with the oxygen atom of one perchlorate ion (Cu-O, 2.36(2) Angstrom). Crystals consist of a racemic mixture of layers of opposite chirality, held together essentially by van der Waals forces. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(99)00179-6
• 作为产物：
  描述：

  4,8-dithiaundecane 在 盐酸 、 二甲基亚砜 作用下， 以 水 为溶剂， 以77%的产率得到1,3-bis(propylsulfinyl)propane
  参考文献：
  名称：

  新型二亚砜及其钌配合物的合成与表征

  摘要：

  摘要报道了通过氧化相应的十种新的二亚砜和四种已知的RS（O）–CH2）n-（O）SR（n = 2或3，R =烷基）形成的合成方法二硫醚，RS（CH2）nSR，使用DMSO或H2O2的酸性溶液作为氧化剂。然后将二氧化硫与市售的RuCl3·H2O，K3（RuCl6）或所谓的Ru'Blue'或'Red'溶液在水溶液或醇（MeOH，EtOH）溶液中反应，从中可以形成各种S键合的亚磺酰基络合物分离出顺式或反式RuIICl2（二亚砜）2型的[RuIICl2（二亚砜）（H2O）] 2（μ-Cl）2和[Ru2II / IIICl（二亚砜）] 2（μ-Cl）3；包括X射线数据在内的所有这三种类型都具有良好的特征。还合成了一种具有桥联二亚砜1,2-双（苯基亚磺酰基）乙烷的RuCl3（BPhSE）] 2（μ-BPhSE）的RuIII配合物，但表征较差。

  DOI：

  10.1016/j.ica.2019.119217

文献信息

• Stereochemical features of the disulfoxides 1,3-bis(n-propylsulfinyl)propane (BPSP) and 1,2-bis(methylsulfinyl)ethane (BMSE), and their copper(II) complexes. Crystal and molecular structure of meso-BPSP, [trans-Cu(meso-BPSP)2(H2O)2](ClO4)2, trans-Cu(meso-BMSE)2(ClO4)2, and trans-Cu(rac-BMSE)2(ClO4)2
  作者：Mario Calligaris、Andrea Melchior、Silvano Geremia

  DOI：10.1016/s0020-1693(01)00597-7

  日期：2001.10

  Diastereomeric meso and rac forms of 1,3-bis(n-propylsulfinyl)propane (BPSP) and 1,2-bis(methylsulfinyl)ethane (BMSE) have been separated and treated with CU(ClO4)(2) to obtain [trans-Cu(meso-BPSP)(2)(H2O)(2)](ClO4)(2) (2) trans-Cu(meso-BMSE)(2)(ClO4)(2) (3) and trans-Cu(rac-BMSE)(2)(ClO4)(2) (4). The configurational assignment to BPSP has been performed by single crystal X-ray analysis, showing that the alpha (m.p. 139.0-139.9 degreesC) and beta (m.p. 107.0-107.6 degreesC) forms correspond to the meso and rac isomers. respectively. Enthalpies of fusion, determined by differential scanning calorimetry techniques, are 34.3 (meso-BMSE), 22.2 (rac-BMSE), 40.6 (meso-BPSP), and 35.1 kJ mol(-1) (rac-BPSP). Single crystals, acceptable for X-ray diffraction studies, were grown by the hanging-drop method of vapor diffusion and micro-seeding techniques. The crystal structure of meso-BPSP.(1) is characterized by an anti conformation of the propane bridge. The two sulfinyl bonds (av. S-O bond distance, 1.487(4) Angstrom) are nearly parallel. In fact, the S --> O vectors form an angle of 2.3 degrees and the pseudo-torsion angle O-S . . .S-O is of 2.2 degrees. Crystals belong to the C2/c space group, with a = 32.285(11), b = 5.315(5), c = 15.232(7) Angstrom, beta = 109.98(3)degrees. The structure was refined to R = 0.092. Crystal data for the copper complexes are space group P2/n, a = 13.914(7), b = 7.834(4), c = 14.805(11) Angstrom, beta = 96.61(5)degrees for 2; space group P2(1)/c, a = 7.348(7), b = 17.892(4), c = 8.620(2) Angstrom, beta = 113.06(2)degrees for 3; space group P2(1)/a, a = 8.343(3), b = 12.337(6), c = 9.390(3) Angstrom, beta = 97.35(3)degrees for 4. The structures were refined to R = 0.066, 0.062, and 0.097 for 2, 3, and 4, respectively. The crystal structures of the meso Cu(II) complexes 2 and 3 are characterized by linear chains of copper atoms, bridged by two disulfoxide molecules acting as bis-monodentate O-ligands. In the rac complex 4, BMSE acts again as a mu (2)-O,O ligand, but forms layers with a net structure containing four copper atoms per mesh, and each layer contains sulfur atoms with both R and S chirality. In the copper complexes the mean S-O bond length is of 1.520(3) Angstrom, confirming the already observed increase in comparison to free sulfoxides. (C) 2001 Elsevier Science BN. All rights reserved.