(2-{[2-(羟基甲基)苯基]硫代}苯基)甲醇 | 38059-09-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: (2-{[2-(羟基甲基)苯基]硫代}苯基)甲醇
• 英文名称: 2,2'-thiobis(benzyl alcohol)
• 英文别名: bis(hydroxymethylphenyl)sulfide；Bis-<2-(hydroxymethyl)-phenyl>-sulfid；Bis(2-hydroxymethylphenyl)sulfid；2,2'-sulfanediyl-di-benzyl alcohol；1-(hydroxymethyl)-2-((6-(hydroxymethyl)phenyl)thio)benzene；2.2'-Bis-oxymethyl-diphenylsulfid；2,2'-Sulfandiyl-di-benzylalkohol；Benzenemethanol,2,2'-thiobis-；[2-[2-(hydroxymethyl)phenyl]sulfanylphenyl]methanol
• CAS: 38059-09-5
• 化学式: C₁₄H₁₄O₂S
• 分子量: 246.33
• InChiKey: JTBORKYQQJPTIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (2-{[2-(羟基甲基)苯基]硫代}苯基)甲醇 在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以3.44 g的产率得到bis(2-hydroxymethylphenyl)sulfoxide
  参考文献：
  名称：

  酶促双（2-羟甲基苯基）亚砜的脱对称化反应作为三齿手性催化剂的途径

  摘要：

  前手性双（2-羟甲基苯基）亚砜3的去对称化是通过通常可获得的脂肪酶促进的乙酰化而有效地进行的。两种脂肪酶，即CAL-B和LPL被证明特别有效地以高达98％的收率和高达98％的ee生成2-乙酰氧基甲基苯基2-羟甲基苯基亚砜4。根据X射线分析，将4的绝对构型确定为（+）-（R）。然后将对映体纯的产物4转化为一系列对映体纯的非对映体2-氨基甲基苯基2-羟甲基苯基亚砜8其中氨基源自具有附加的C-立体异构中心的对映体纯的胺。在二乙基锌与苯甲醛的参比反应中，以尽可能高的收率和高达50％的ee值，将化合物8作为三齿手性催化剂作为可能的三齿手性催化剂进行了研究。

  DOI：

  10.1016/j.tetasy.2008.08.017
• 作为产物：
  描述：

  硫代水杨酸 在 copper(l) iodide 、 硼烷四氢呋喃络合物 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 18.0h， 生成 (2-{[2-(羟基甲基)苯基]硫代}苯基)甲醇
  参考文献：
  名称：

  发现苄基异硫脲作为有效的二价金属转运蛋白1（DMT1）抑制剂

  摘要：

  抑制肠刷缘DMT1为预防和治疗铁超负荷疾病提供了一种新颖的治疗方法。从最初的化合物1中发现了一些系列的二芳基和三环苄基异硫脲化合物作为新型和有效的DMT1抑制剂。这些化合物在铁超吸收的急性大鼠模型中表现出对DMT1的体外效力，所需的细胞通透性和铁吸收的剂量依赖性抑制。三环化合物将体外效价提高了16倍。二芳基化合物6b和14a在25和50 mg / kg剂量下均显示出明显的体内铁吸收抑制作用。本报告中描述的二芳基和三环化合物代表了有希望的结构模板，可用于进一步优化。

  DOI：

  10.1016/j.bmcl.2012.05.129

文献信息

• BIARYL AND BIHETEROARYL COMPOUNDS USEFUL IN TREATING IRON DISORDERS
  申请人：Chafeev Mikhail

  公开号：US20080234384A1

  公开（公告）日：2008-09-25

  This invention is directed to compounds of formula (I): wherein m, n, R 1 , R 2 and R 3 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment of iron disorders. This invention is also directed to pharmaceutical compositions comprising the compounds and methods of using the compounds to treat iron disorders.

  本发明涉及以下式（I）的化合物：其中m、n、R1、R2和R3如本文中所定义，作为立体异构体、对映异构体、互变异构体或其混合物；或其药学上可接受的盐、溶剂化合物或前药，用于治疗铁代谢紊乱。本发明还涉及包含这些化合物的药物组合物以及使用这些化合物治疗铁代谢紊乱的方法。
• Efficient catalysts for asymmetric Mannich reactions
  作者：Michał Rachwalski、Tim Leenders、Sylwia Kaczmarczyk、Piotr Kiełbasiński、Stanisław Leśniak、Floris P. J. T. Rutjes

  DOI：10.1039/c3ob40681d

  日期：——

  Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields and excellent enantio- and diastereoselectivities. The reaction conditions have been optimized by invoking ultrasonication and the influence of some structural moieties of the catalysts on the chemical yield and stereoselectivity of the Mannich products has been evaluated.

  针对酮、醛和胺（对甲氧基苯胺）的直接不对称三组分曼尼希反应开发了高效手性催化剂。获得了相应的 β-氨基羰基化合物（曼尼希加合物），化学收率高，对映和非对映选择性极佳。通过使用超声波对反应条件进行了优化，并评估了催化剂的某些结构分子对曼尼希产物的化学收率和立体选择性的影响。
• Reactions of Sulfoxides Bearing ortho-Sulfur Functional Groups and Thianthrene Monooxide with Grignard Reagents
  作者：Naomichi Furukawa、Satoshi Ogawa、Kazunori Matsumura、Tadao Shibutani、Hisashi Fujihara

  DOI：10.1246/cl.1990.979

  日期：1990.6

  Diaryl sulfoxides bearing ortho-sulfur substituents react readily with Grignard reagents on the sulfur atom to produce the corresponding phenyl Grignard reagents bearing ortho-sulfur functional group. Furthermore, thianthrene monooxide was found to react with alkyl Grignard reagents affording o,o′-bis-Grignard reagent of diphenyl sulfide which was converted easily to Martin’s sulfurane.

  带有邻硫取代基的二芳基亚砜很容易与硫原子上的格氏试剂反应，生成相应的带有邻硫官能团的苯基格氏试剂。此外，发现一氧化噻蒽与烷基格氏试剂反应，得到二苯硫醚的 o,o'-双-格氏试剂，该试剂很容易转化为 Martin's 硫烷。
• Raguse, Burkhard; Ridley, Damon D., Australian Journal of Chemistry, 1988, vol. 41, # 12, p. 1943 - 1952
  作者：Raguse, Burkhard、Ridley, Damon D.

  DOI：——

  日期：——
• Study on the intramolecular transannular chalcogen–tin interactions in dithiastannecine compounds
  作者：Diego Martínez-Otero、José G. Alvarado-Rodríguez、Julián Cruz-Borbolla、Noemí Andrade-López、Thangarasu Pandiyan、Rafael Moreno-Esparza、Marcos Flores-Alamo、Jesús Cantillo-Castillo

  DOI：10.1016/j.poly.2011.11.053

  日期：2012.2

  Dithiastannecine compounds of the type [D(C6H4CH2S)(2)}(SnRR2)-R-1] with different donor atoms D were prepared, where D = O and R-1 = R-2 = Ph (4a); R-1 = Ph, R-2 = Cl (5a); R-1 = n-Bu, R-2 = Cl (6a); D = S and R-1 = R-2 = Ph (4b): R-1 = Ph, R-2 = Cl (5b); R-1 = n-Bu, R-2 = Cl (6b). The molecular structures of the monochloro compounds 5a, 51). 6a, and 6b were established by single-crystal X-ray diffraction and exhibit trigonal bipyramidal geometry at the tin atom with different degrees of distortion being due a D center dot center dot center dot Sn interaction. The Spiro compounds [D(C6H4CH2S)(2)}(2)Sn] with D = O (7a) and D = S (7b) were also synthesized and structurally characterized; the molecular structure of 7a showed the tin atom with a bicapped tetrahedral geometry. The behavior of all tin compounds in solution was investigated by NMR spectroscopy revealing that the D center dot center dot center dot Sn interaction in solution was practically absent on the basis of the NMR chemical shifts values. DFT calculations with ADF package using VWN/QZ4P were carried out for the 6a and 6b compounds and showed that, in the topological analysis, bond critical points are present along the D center dot center dot center dot Sn direction. (C) 2011 Elsevier Ltd. All rights reserved.