4-bromo-2,2-dimethyl-2H-thiochromene | 154324-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 4-bromo-2,2-dimethyl-2H-thiochromene
• 英文别名: 4-Bromo-2,2-dimethylthiochromene
• CAS: 154324-94-4
• 化学式: C₁₁H₁₁BrS
• 分子量: 255.178
• InChiKey: RNPIOQHWUXYCNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-2,2-dimethyl-2H-thiochromene 在 正丁基锂 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 0.47h， 生成 (+/-)-8,9-dimethoxy-6,6-dimethyl-6,6a-dihydroindeno[1,2-c]thiochromene
  参考文献：
  名称：

  Application of Nazarov type electrocyclization to access [6,5,6] and [6,5,5] core embedded new polycycles: an easy entry to tetrahydrofluorene scaffolds related to Taiwaniaquinoids and C-nor-D homosteroids

  摘要：

  在相对温和和催化的纳扎罗夫型电环化条件下，已经实现了一种简单、高效且简洁的方法，用于合成嵌入新多环的四氢氟烯[6,5,6]ABC三环核心，使用2 mol% Sc(OTf)3在无水DCM（氯仿）中于室温反应，获得了高产率。通过合成嵌入稀有异三环[6,5,5]ABC骨架的多样化多环，展示了该反应的普遍性。

  DOI：

  10.1039/c0ob00892c
• 作为产物：
  描述：

  2,2-二甲基-2,3-二氢-1-苯并噻喃-4-酮 在 三溴化磷 作用下， 反应 0.67h， 以71%的产率得到4-bromo-2,2-dimethyl-2H-thiochromene
  参考文献：
  名称：

  合成和反应性一些4-溴-2- ħ -chromenes和2 ħ -thiochromenes

  摘要：

  描述了由相应的酮和PBr 3容易地合成4-溴-2 H-色烯和2 H-硫代色烯以及1-溴-3,4-二氢萘。在某些情况下，分离出大量的膦酸（3）。溴化合物向硫代衍生物的转化提供了广泛的新颖的4-取代的2 H-色烯和2 H-硫代色烯的途径。

  DOI：

  10.1016/s0040-4020(01)86967-2

文献信息

• Application of Nazarov cyclization to access [6-5-6] and [6-5-5]tricyclic core embedded new heterocycles: an easy entry to structures related to Taiwaniaquinoids
  作者：Ritesh Singh、Maloy Kumar Parai、Gautam Panda

  DOI：10.1039/b901632e

  日期：——

  A concise and general route to synthesize a new class of [6-5-6] tricyclic core embedded polyheterocycles has been accomplished using diastereoselective Nazarov cyclization with an overall yield of 35–40%. Versatility of this synthetic route has also been demonstrated by accessing a variety of [6-5-5] tricyclic core incorporated polycycles. It was observed that the efficiency of cyclization depends

  使用非对映选择性纳扎罗夫环化法合成了一种新型的[6-5-6]三环核嵌入多杂环化合物的简洁而通用的方法，其总收率为35-40％。通过使用各种[6-5-5]三环掺入核心的多环化合物也证明了这种合成途径的多功能性。观察到环化效率取决于极化对反应体系的影响。在筛选用于环化的各种路易斯酸和布朗斯台德酸中，三氟甲磺酸 被发现是最有效的催化剂。
• Synthesis and reactivity of some 4-bromo- 2H-chromenes and 2H-thiochromenes
  作者：Christopher D Gabbutt、David J Hartley、John D Hepworth、B.Mark Heron、Magan Kanjia、M.Moshfiqur Rahman

  DOI：10.1016/s0040-4020(01)86967-2

  日期：1994.2

  synthesis of 4-bromo- 2H-chromenes and 2H-thiochromenes and of 1-bromo-3,4-dihydronaphthalene from the corresponding ketones and PBr3 is described. In some instances, significant quantities of the phosphonic acids (3) are isolated. Conversion of the bromo compounds to the lithio derivatives provides access to a wide range of novel 4-substituted 2H-chromenes and 2H-thiochromenes.

  描述了由相应的酮和PBr 3容易地合成4-溴-2 H-色烯和2 H-硫代色烯以及1-溴-3,4-二氢萘。在某些情况下，分离出大量的膦酸（3）。溴化合物向硫代衍生物的转化提供了广泛的新颖的4-取代的2 H-色烯和2 H-硫代色烯的途径。
• Reactions of some 2H-Chromenes and 2H-Thiochromenes with triazolinediones
  作者：Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/0040-4020(95)00874-8

  日期：1995.11

  Simple 2H-chromenes and 2H-thiochromenes form the [2+2]-adducts, tetrahydro[1]benzo(thio)pyrano[3,4-c] [1,2]diazeto[1,2-a][1,2,4]triazoles, with triazolinediones, whereas their 3- and 4-bromo and the corresponding cycloalkylamino derivatives undergo an overall etectrophilic substitution sequence.

  简单的2 ħ -chromenes和2个ħ -thiochromenes形成[2 + 2] -adducts，四氢[1]苯并（硫）吡喃并[3,4- c ^ ] [1,2] diazeto [ 1，2-一个] [ 1,2，4 ]三唑，与triazolinediones，而他们的3-和4 -溴和相应的环烷基的衍生物经历的整体etectrophilic替代序列。
• Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 653 - 658
  作者：Gabbutt, Christopher D.、Hepworth, John D.、Heron, B. Mark

  DOI：——

  日期：——
• An unexpected reaction of phosphorous tribromide on chromanone, thiochromanone, 3,4-dihydro-2H-benzo[b]thiepin-5-one, 3,4-dihydro-2H-benzo[b]oxepin-5-one and tetralone derived allylic alcohols: a case study
  作者：Maloy K. Parai、Shagufta、Ajay K. Srivastava、Matthias Kassack、Gautam Panda

  DOI：10.1016/j.tet.2008.07.106

  日期：2008.10

  Treatment of chromanone, thiochromanone, tetralone and benzo[b]thiepinone derived allylic alcohols with phosphorous tribromide furnished unexpected products instead of desired bromo derivatives. Reaction of 7-methoxy-2,2-dimethylchromenyl-aryl-methanols and 7-methoxy-2,2-dimethylthio-chromenyl-aryl-methanols with PBr3 gave saturated carbonyls and exocyclic olefins depending on the substituents at R-4, whereas allylic alcohols without 7-methoxy substituent furnished rearranged products. Several related analogs varying in ring size, heteroatom in the ring and substituents at various positions were synthesized and studied. Reactions of other phosphorous-based reagents like PPh3, PPh3/I-2 and PPh3Br2 on allylic alcohols were also attempted. A case study is presented here. (C) 2008 Elsevier Ltd. All rights reserved.