1-异硫氰基-2-(2-异硫氰基乙氧基)乙烷 | 103144-36-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 中文名称: 1-异硫氰基-2-(2-异硫氰基乙氧基)乙烷
• 英文名称: 1-isothiocyanato-2-[2-(isothiocyanato)ethoxy]ethane
• 英文别名: 3-oxapentamethylenediisothiocyanate；1,9-dithioxo-5-oxa-2,8-diazanonane；Ethane, 1,1'-oxybis[2-isothiocyanato-；1-isothiocyanato-2-(2-isothiocyanatoethoxy)ethane
• CAS: 103144-36-1
• 化学式: C₆H₈N₂OS₂
• 分子量: 188.274
• InChiKey: BISOMDWMNMKPEL-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 1 Torr)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-异硫氰基-2-(2-异硫氰基乙氧基)乙烷 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 3,9-dimethyl-1,3,9,11-tetraaza-6,14,17,22-tetraozabicyclo<9.8.5>tetracosane-2,10-dione
  参考文献：
  名称：

  Luk'yanenko, N. G.; Kirichenko, T. I.; Shcherbakov, S. V., Journal of Organic Chemistry USSR (English Translation), 1986, p. 1589 - 1593

  摘要：

  DOI：
• 作为产物：
  描述：

  110.0~130.0 ℃ 、4.0 kPa 条件下， 生成 1-异硫氰基-2-(2-异硫氰基乙氧基)乙烷
  参考文献：
  名称：

  Novel cryptands containing thiourea units as a part of the macrocyclic framework

  摘要：

  通过终端卤素取代的N-取代邻苯二甲酰亚胺对二氮-18-冠-6进行烷基化，并随后与水合肼和酸水解反应，得到了相应的N,N′-二取代二氮-18-冠-6化合物，其侧链中含有终端主要氨基。将这些化合物与二硫化碳或适当的双[寡（乙烯氧基）]异硫氰酸酯反应，得到了一系列新型的克里普坦，其中一条桥中含有一个或两个硫脲单位。

  DOI：

  10.1039/b207902j

文献信息

• Design of a Neutral Macrocyclic Ionophore: Synthesis and Binding Properties for Nitrate and Bromide Anions
  作者：Rainer Herges、Anton Dikmans、Umasish Jana、Felix Köhler、Peter G. Jones、Ina Dix、Tom Fricke、Burkhard König

  DOI：10.1002/1099-0690(200209)2002:17<3004::aid-ejoc3004>3.0.co;2-o

  日期：2002.9

  A macrocyclic neutral ionophore 8 (X = O) capable of binding weakly coordinating anions such as nitrate and bromide in DMSO solution has been designed by a stepwise, deductive approach. The optimum geometrical arrangement of the hydrogen bond donor sites in the target ionophore was determined by DFT calculations. From these data, a suitable macrocyclic molecular framework was constructed. The 24-membered

  一种大环中性离子载体 8 (X = O) 能够在 DMSO 溶液中结合弱配位阴离子，如硝酸盐和溴化物，已通过逐步、演绎的方法设计出来。目标离子载体中氢键供体位点的最佳几何排列由 DFT 计算确定。根据这些数据，构建了合适的大环分子框架。24 元大环离子载体是通过标准的大环化方法合成的。NMR 滴定显示，在 DMSO 中，8 (X = O) 与硝酸盐、硫酸氢盐、醋酸盐、氰化物、碘化物和溴化物离子形成了具有定义的 1:1 化学计量的分子复合物，而磷酸二氢盐、硫酸盐和氯离子则产生了更高化学计量的聚集体。对于在纯 DMSO 溶液中具有确定结合位点的中性离子载体，硝酸盐结合常数为 8 (X = O) 是重要的。具有相似离子半径的溴离子以更高的亲和力结合。氯化物显然太小，碘太大，无法形成 1:1 的配合物。将 8 (X = O) 的结合基序与类似结构的相关分子，如 8 (X = S) 和 19 进行比较。
• POLYMERIZABLE COMPOSITION FOR POLYTHIOURETHANE OPTICAL MATERIAL
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1988109A1

  公开（公告）日：2008-11-05

  A polymerizable composition for polythiourethane optical materials comprising a compound represented by the general formula (1),         M(L)n     (1) wherein, in the formula, M is Al, Fe, Cu, Zn, Zr or Bi; L is a dithiocarbamic acid group, a sulfonic acid group, a mono- or di-alkyl phosphoric acid ester group, a substituted acetylacetonato group or a halogen; and n is an integer of 1 to 5, one or two or more isocyanates selected from the group consisting of isocyanate compounds and isothiocyanate compounds, and one or two or more active hydrogen compounds each having a mercapto group. The compounds represented by the general formula (1) exhibit catalytic activity equal to or superior to that of organotin catalysts having been employed as catalysts for the production of polythiourethane optical materials from the past, and have high safety. Further, the thus obtained polythiourethane resins satisfactorily meet the property requirements for optical materials, in particular, excelling in weather resistance. Therefore, the proposed catalysts are available as novel catalysts replacing the organotin catalysts.

  一种用于聚硫乙烷光学材料的可聚合组合物，由通式 (1) 所代表的化合物组成、 M(L)n (1) 式中，M 是 Al、Fe、Cu、Zn、Zr 或 Bi；L 是二硫代氨基甲酸基团、磺酸基团、单烷基或二烷基磷酸酯基团、取代的乙酰丙酮基团或卤素；n 是 1 至 5 的整数、 一种或两种或多种异氰酸酯，选自异氰酸酯化合物和异硫氰酸酯化合物组成的组，以及 一种或两种或多种活性氢化合物，每种活性氢化合物都带有一个巯基。通式（1）所代表的化合物的催化活性等同于或优于过去用作生产聚硫乙烷光学材料催化剂的有机锡催化剂，而且安全性高。此外，由此获得的聚硫乙烷树脂还能满足光学材料的性能要求，特别是在耐候性方面表现出色。因此，所提出的催化剂可作为新型催化剂替代有机锡催化剂。
• POLYMERIZATION CATALYST FOR POLYTHIOURETHANE OPTICAL MATERIAL, POLYMERIZABLE COMPOSITION CONTAINING THE CATALYST, POLYTHIOURETHANE RESIN OBTAINED FROM THE COMPOSITION, AND METHOD FOR PRODUCING THE RESIN
  申请人：Mitsui Chemicals, Inc.

  公开号：EP2065414A1

  公开（公告）日：2009-06-03

  By using an amine hydrochloride represented by the formula (1) as a catalyst, a polythiourethane resin which is suitably used for a transparent resin for optical use, can be obtained without using an organotin compound which has been conventionally used as a catalyst for polythiourethane resins and without being affected by the acidity of an additive: wherein R1, R2 and R3 independently represent a monovalent or higher valent linear aliphatic, branched aliphatic, cyclic aliphatic or aromatic organic residue which may have a hydroxyl group or an amino group; and R1, R2 and R3 may be arbitrarily bonded to each other to form a ring.

  使用由式（1）表示的胺盐酸盐作为催化剂，可以获得一种适合用于光学用透明树脂 的聚硫氨酸树脂，而无需使用传统上用作聚硫氨酸树脂催化剂的有机锡化合物，也不会 受到添加剂酸性的影响： 其中 R1、R2 和 R3 独立地代表一价或更高价的线性脂肪族、支链脂肪族、环状脂肪族或芳香族有机残基，可带有羟基或氨基；R1、R2 和 R3 可任意地相互键合以形成环。
• POLYMERIZATION CATALYST FOR POLYTHIOURETHANE OPTICAL MATERIAL, POLYMERIZABLE COMPOSITION CONTAINING THE CATALYST, OPTICAL MATERIAL OBTAINED FROM THE COMPOSITION, AND METHOD FOR PRODUCING THE OPTICAL MATERIAL
  申请人：Mitsui Chemicals, Inc.

  公开号：EP2116558A1

  公开（公告）日：2009-11-11

  The polymerization catalyst for a polythiourethane-based optical material of the present invention includes a sulfonate represented by the following general formula (1). Furthermore, in the formula, R1, R2, R3 and R4 each independently represent an alkyl group having 1 to 18 carbon atoms, R1, R2, R3 and R4 may be bonded to each other to form a ring. R5 represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and X represents a nitrogen atom or a phosphorus atom.

  本发明聚硫乙烷基光学材料的聚合催化剂包括由以下通式（1）表示的磺酸盐。此外，在该式中，R1、R2、R3 和 R4 各自独立地代表具有 1 至 18 个碳原子的烷基，R1、R2、R3 和 R4 可相互键合形成环。R5 代表氢原子或具有 1 至 18 个碳原子的烷基，X 代表氮原子或磷原子。
• Polymerizable composition for polythiourethane optical material, polythiourethane optical material obtained from the polymerizable composition, and polymerization catalyst for polythiourethane optical material
  申请人：Mitsui Chemicals, Inc.

  公开号：EP2407498A2

  公开（公告）日：2012-01-18

  The polymerizable composition for a polythiourethane optical material of the present invention includes (A) a polymerization catalyst for a polythiourethane optical material, (B) at least one compound selected from an isocyanate compound and an isothiocyanate compound, and (C) a compound containing one or more mercapto groups, wherein said polymerization catalyst for a polythiourethane optical material (A) includes (a1) a zinc compound, and (a4)a compound represented by the following general formula (4).

  本发明的聚硫乙烷光学材料可聚合组合物包括 (A) 聚硫乙烷光学材料聚合催化剂，(B) 至少一种选自异氰酸酯化合物和异硫氰酸酯化合物的化合物，以及 (C) 含有一个或多个巯基的化合物，其中所述聚硫乙烷光学材料聚合催化剂 (A) 包括 (a1) 一种锌化合物，以及 (a4) 一种由下式通式 (4) 表示的化合物。