1-羟基-2,3-二氢-1H-茚-2-基硫氰酸酯 | 379668-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 1-羟基-2,3-二氢-1H-茚-2-基硫氰酸酯
• 中文别名: 氰硫基&lt硫代氰酸基&gt酸,2,3-二氢-1-羟基-1H-茚-2-基酯
• 英文名称: 2-thiocyanato-2,3-dihydro-1H-inden-1-ol
• 英文别名: (1-hydroxy-2,3-dihydro-1H-inden-2-yl) thiocyanate
• CAS: 379668-79-8
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: FPKWSZJQQMIGAP-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 2-phenyl-2-(2-pyridyl)imidazolidine 作用下， 以 乙腈 为溶剂， 反应 1.33h， 生成 1-羟基-2,3-二氢-1H-茚-2-基硫氰酸酯 、 2-羟基-2,3-二氢-1H-茚-1-基硫氰酸酯
  参考文献：
  名称：

  2-Phenyl-2-(2-pyridyl)imidazolidine (PPI) 作为新催化剂在环氧化物与硫氰酸铵的高效、温和和区域选择性转化中

  摘要：

  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。

  DOI：

  10.1080/10426500307906

文献信息

• One-pot anodic thiocyanation and isothiocyanation of alkenes
  作者：Avishai Levy、James Y. Becker

  DOI：10.1016/j.electacta.2015.07.127

  日期：2015.10

  The one-pot anodic thiocyanation and isothiocyanation of alkenes in both acidic two-phase (water-dichloromethane) and homogeneous one-phase (water-acetonitrile) media has been studied. Optimisation experiments on tetramethylethylene as a model alkene involved the use of different acids, anodes, current densities, charge consumption and electrolysis methods. In the two-phase medium mainly two addition

  研究了酸性两相（水-二氯甲烷）和均相一相（水-乙腈）介质中烯烃的一锅阳极硫氰化和异硫氰化反应。以四甲基乙烯为模型烯烃的优化实验涉及使用不同的酸，阳极，电流密度，电荷消耗和电解方法。在两相培养基中，主要形成了两个加成产物（中等产量）的SCN / NCS（主要）和两个SCN / SCN组。其他烷基取代的烯烃也产生类似的加成产物，但是涉及两个SCN基团的那些成为主要的。此外，还观察到烯丙基硫氰酸根和异硫氰酸根取代产物，但收率较低。活化的烯烃（例如苯乙烯，茚和丁基乙烯基醚）未生成加成产物，而1， 在均相一相乙腈水溶液中，包括苯乙烯和茚的所有情况下，SCN / OH加合物的形成都变得突出。他们还提供了相应的SCN / SCN和SCN / NCS加成产品。然而，1，1-二苯基乙烯给出了唯一的乙烯基取代产物，而2，3-二甲基呋喃没有反应。
• 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。
• 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.