2-((benzylthio)methyl)oxirane | 20256-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((benzylthio)methyl)oxirane
• 英文别名: 2-(benzylsulfanylmethyl)oxirane；benzylsulfanylmethyl-oxirane；2-[(Benzylsulfanyl)methyl]oxirane
• CAS: 20256-77-3
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: CRQGYWVOLVTOKD-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 0.5 Torr)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((benzylthio)methyl)oxirane 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 1-(benzylthio)-3-((1S,5R)-8-oxo-1,5,6,8-tetrahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocin-3(4H)-yl)propan-2-yl 4-nitrobenzoate
  参考文献：
  名称：

  基于结构的筛选和优化作为半胱氨酸-MLL相互作用抑制剂的半胱氨酸衍生物

  摘要：

  通过计算机筛选，将天然产物样化合物1鉴定为menin-MLL相互作用的直接抑制剂。基于结构的优化提供了类似物1a，其效能远高于...

  DOI：

  10.1039/c6cc01079b
• 作为产物：
  描述：

  1-benzylsulfanyl-3-chloro-propan-2-ol 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以81.8%的产率得到2-((benzylthio)methyl)oxirane
  参考文献：
  名称：

  Stereochemistry and regiochemistry of heteroatom directed reactions. 5. The first practical method of selective heteroatom-directed chlorohydroxylation

  摘要：

  A new Pd(II)-catalyzed nucleophilic chlorohydroxylation reaction of allylic amines and sulfides was achieved, and the regioselective reaction gives high yields of the chlorohydrin products, which can be transformed into epoxy compounds or aziridine compounds by simple manipulations.

  DOI：

  10.1021/jo00077a003

文献信息

• METHOD FOR PRODUCING SULFUR-CONTAINING EPOXY COMPOUND
  申请人：MITSUBISHI GAS CHEMICAL COMPANY, INC.

  公开号：US20140371475A1

  公开（公告）日：2014-12-18

  An object of the present invention is to provide a method for producing a sulfur-containing epoxy compound producing no scum-like insoluble matter. According to the present invention, a sulfur-containing halohydrin compound is dripped into and reacted with a mixed solvent containing an organic solvent and a basic compound to provide the method for producing the sulfur-containing epoxy compound. According to aspects of the present invention, the organic solvent is at least one type of compound selected from toluene and benzene, the basic compound is at least one type of compound selected from sodium hydroxide, potassium hydroxide and calcium hydroxide, and the reaction temperature is between −5° C. and 30° C.

  本发明的目的是提供一种生产含硫环氧化合物且不产生类似沉渣般不溶物的方法。根据本发明，将含硫卤代醇化合物滴入并与含有有机溶剂和碱性化合物的混合溶剂反应，以提供生产含硫环氧化合物的方法。根据本发明的方面，有机溶剂至少是从甲苯和苯中选择的一种化合物，碱性化合物至少是从氢氧化钠、氢氧化钾和氢氧化钙中选择的一种化合物，反应温度在-5℃和30℃之间。
• Zur Reaktion von monosubstituierten Epoxypropanen mit Benzylamin. 1. Mitteilung über Ringöffnungsreaktionen kleiner Ringe
  作者：Ueli Sulser、Jürg Widmer、Heinz Goeth

  DOI：10.1002/hlca.19770600523

  日期：1977.7.13

  Reaction of monosubstituted epoxypropanes with benzylamine

  单取代环氧丙烷与苄胺的反应
• Verfahren zur Herstellung von Glycidythioethern
  申请人：CIBA-GEIGY AG

  公开号：EP0166695A2

  公开（公告）日：1986-01-02

  Verfahren zur Herstellung von Glycidylthioethern der Formel dadurch gekennzeichnet, dass Epichlorhydrin mit einem Mercaptan der Formel II worin R einen Rest sein kann, worin R1, R2 und R3 unabhängig voneinander C,-C18 Alkyl sind und zusammen nicht mehr als 22 C-Atome besitzen und R2 und R3 ausserdem Wasserstoff sind oder worin R C5-C6 Cycloalkyl, unsubstituiertes oder durch C1-C4 Alkyl substituiertes Phenyl oder Naphthyl, Benzyl, Furfuryl ist, oder worin R C2-C8 Alkylen bedeutet, das durch -SH substituiert ist und gegebenenfalls durch 1 oder 2 Ether-O-Atome unterbrochen sein kann, in aequimolarer Menge ohne organisches Lösungsmittel in Gegenwart einer Base nach dem Phasentransferkatalyseverfahren, wobei ein Phasentransferkatalysator eingesetzt wird, bei einer Temperatur von -30°C bis +20°C umgesetzt wird. Die so hergestellten Glycidylthioether sind Verbindungen, die in der Synthese von organischen Schwefelverbindungen eine wichtige Rolle spielen, die beispielsweise als Schmiermitteladditive Verwendung finden.

  一种制备式 1 的缩水甘油硫醚的工艺 其特征在于环氧氯丙烷与式 II 的硫醇反应，其中 R 可以是自由基 其中 R1、R2 和 R3 相互独立地为 C,-C18烷基，且合在一起不超过 22 个碳原子，R2 和 R3 也是氢，或其中 R 为 C5-C6 环烷基、未取代的或 C1-C4 烷基取代的苯基或萘基、苄基、糠基，或其中 R 为 C2-C8 亚烷基、的缩水甘油硫醚，在不使用有机溶剂的情况下，按照相转移催化工艺（其中使用了相转移催化剂），在-30°C 至 +20°C的温度下，在碱存在下以等摩尔量进行反应。以这种方法生产的缩水甘油硫醚是一种在合成有机硫化合物（例如用作润滑油添加剂）过程中起重要作用的化合物。
• Regiochemical and stereochemical studies on halocyclization reactions of unsaturated sulfides
  作者：Xiao-Feng Ren、Edward Turos、Charles H. Lake、Melvyn Rowen Churchill

  DOI：10.1021/jo00125a038

  日期：1995.10

  The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent. Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts. The endo- versus exo-regioselectivity of these alkenyl sulfide ring closures most likely reflects the difference in thermodynamic stabilities of the beta-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate. The efficiency of the cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers. Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides. Conversely the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length. Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring, The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control. The methodology has been applied to the synthesis of unusual bicyclic beta-lactams related to the penicillin family of antibiotics.
• Al(OTf)₃-Mediated Epoxide Ring-Opening Reactions: Toward Piperazine-Derived Physiologically Active Products
  作者：D. Bradley G. Williams、Adam Cullen

  DOI：10.1021/jo9020437

  日期：2009.12.18

  Al(OTf)(3) is a good catalyst for the ring opening of epoxides, forming beta-amino alcohols bearing the piperazine motif. Two different strategies were examined, where the glycidyl ether resided on one-half of the molecule or the other, allowing insight into a best-case approach for the ring-opening step. Each half of the molecule contained an heteroatom that could be used either to attach the glycidyl moiety or as the nucleophile in the ring-opening reaction, for the same set of reagents, allowing this approach.