2-羟基-2,3-二氢-1H-茚-1-基硫氰酸酯 | 379668-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2-羟基-2,3-二氢-1H-茚-1-基硫氰酸酯
• 中文别名: 氰硫基&lt硫代氰酸基&gt酸,2,3-二氢-2-羟基-1H-茚-1-基酯
• 英文名称: 2-hydroxy-1-indanyl thiocyanate
• 英文别名: 2-hydroxy-1-thiocyanatoindan；2-Hydroxy-2,3-dihydro-1H-inden-1-yl thiocyanate；(2-hydroxy-2,3-dihydro-1H-inden-1-yl) thiocyanate
• CAS: 379668-80-1
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: PVOPIBUAJMFTFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫氰酸铵 、 氧化茚 在 zinc ferrite 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以90%的产率得到2-羟基-2,3-二氢-1H-茚-1-基硫氰酸酯
  参考文献：
  名称：

  ZnFe2O4 纳米颗粒：一种绿色且可回收的磁性催化剂，用于在无溶剂条件下使用 NH4SCN 将环氧化物快速区域选择性地转化为邻位羟基硫氰酸酯

  摘要：

  图形摘要 摘要 ZnFe2O4 纳米颗粒被合成并用作可回收磁性催化剂，在室温下用NH4SCN 将不同环氧化物无溶剂转化为邻位羟基硫氰酸酯。反应是通过在研钵中研磨进行的，在短时间内（2-25 分钟）具有完美的区域选择性，并且具有高到极好的收率（75-95%）。使用外部磁铁可以轻松分离纳米催化剂，并连续重复使用四个循环，而没有任何明显的效率或磁性损失。

  DOI：

  10.1080/10426507.2017.1390460

文献信息

• Schiff-Base Metal(II) Complexes as New Catalysts in the Efficient, Mild and Regioselective Conversion of 1,2-Epoxyethanes to 2-Hydroxyethyl Thiocyanates with Ammonium Thiocyanate
  作者：Hashem Sharghi、Mohammad Ali Nasseri

  DOI：10.1246/bcsj.76.137

  日期：2003.1

  A convenient and efficient procedure for the ring-opening of 1,2- epoxyethanes with ammonium thiocyanate in the presence of some Schiff-base complexes of metal(II) is described. The cleavage of the oxirane ring is found to proceed regioselectively under mild reaction conditions. Thus, several 2-hydroxyethyl thiocyanates, useful intermediates toward biological-active molecules, are easily obtained in very good yields.

  本文描述了一种在金属（II）的一些席夫碱配合物的存在下，用硫氰酸铵开环1,2-环氧乙烷的便捷高效方法。研究发现，在温和的反应条件下，环氧乙烷环的断裂是按位点选择性进行的。因此，几种2-羟乙基硫氰酸酯（生物活性分子的重要中间体）可以很容易地以很高的收率获得。
• 2-Phenyl-2-(2-pyridyl)imidazolidine (PPI) as New Catalyst in the Efficient, Mild, and Regioselective Conversion of Epoxides to Thiocyanohydrines with Ammonium Thiocyanate
  作者：Hashem Sharghi、Mohammad Ali Nasseri

  DOI：10.1080/10426500307906

  日期：2003.6

  2-Phenyl-2-(2-pyridyl)imidazolidine (PPI) catalysis the addition of thiocyanate ion to epoxides to afford g -hydroxy thiocyanate in high yields, mild conditions, and regioselectivity. Thus, several 2-hydroxyethyl thiocyanates, which are useful intermediates toward biological active molecules, are obtained easily in very good yields.

  2-苯基-2-(2-吡啶基)咪唑烷 (PPI) 催化硫氰酸根离子与环氧化物的加成，以高产率、温和条件和区域选择性提供 g-羟基硫氰酸盐。因此，可以很容易地以非常好的收率轻松获得几种 2-羟乙基硫氰酸酯，它们是生物活性分子的有用中间体。
• Phenol-Containing Macrocyclic Diamides as New Catalysts in the Highly Regioselective Conversion of Epoxides to β-Hydroxy Thiocyanates
  作者：Hashem Sharghi、Mohammad Ali Nasseri、Khodabakhsh Niknam

  DOI：10.1021/jo0103266

  日期：2001.11.1

  The regioselective ring-opening reactions of some epoxides with ammonium thiocyanate in the presence of a series of new phenol-containing macrocyclic diamides and also dibenzo-18-crown-6-, 18-crown-6-, benzo-15-crown-5-, and pyridine-containing macrocyclic diamide have been studied. The epoxides were subject to cleavage by NH4SCN in the presence of these catalysts under mild reaction conditions in various aprotic solvents. In this study, reagents and conditions have been discovered with which the individual beta -hydroxy thiocyanates can be synthesized in high yield and with more than 90% regioselectivity. The results can be discussed in terms of a four-step mechanism: (1) formation of complex between catalyst and NH4SCN, (2) release of SCN- nucleophile from the complex, (3) reaction of the active nucleophile at the less sterically hindered site in the epoxide, and (4) regeneration of catalyst. The major advantages of this method are as follows: (1) high regioselectivity, (2) simple regeneration of catalyst, (3) its reuse through several cycles without a decrease in activity, and (4) ease of workup of the reaction.
• Selectfluor™: a novel and efficient reagent for the synthesis of β-hydroxy thiocyanates
  作者：J.S. Yadav、B.V.S. Reddy、Ch.Srinivas Reddy

  DOI：10.1016/j.tetlet.2003.11.102

  日期：2004.2

  A variety of epoxides undergo rapid ring opening with ammonium thiocyanate in the presence of 10 mol% Selectfluor(TM) in acetonitrile at room temperature to afford the corresponding beta-hydroxy thiocyanates in excellent yields with high regioselectivity. (C) 2003 Elsevier Ltd. All rights reserved.
• CONVERSION OF EPOXIDES INTO 2-HYDROXYETHYL THIOCYANATES WITH NH₄SCN IN THE PRESENSE OF 2,6-BIS[2-(<i>O</i> -AMINO PHENOXY)METHYL]-4-BROMO-1-METHOXYBENZENE (BABMB) AS CATALYST
  作者：Khodabakhsh Niknam

  DOI：10.1080/10426500490262685

  日期：2004.3.1

  A convenient and efficient procedure for the ring-opening of 1,2-epoxyethanes with ammonium thiocyanate in the presence of 2,6-bis[2(o-aminophenoxy)methyl]-4-bromo-1-methoxybenzene (BABMB) is described. In this study, a reagent and conditions have been discovered with which the individual 2-hydroxyethyl thiocyanates can be synthesized in high yield and with more than 90% regioselectivity. Thus several 2-hydroxyethyl thiocyanates, useful intermediates toward biological-active molecules, are easily obtained in very good yields.