3-isopropyl-4-vinyl-3,6-dihydro-2H-thiopyran | 1374576-64-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 3-isopropyl-4-vinyl-3,6-dihydro-2H-thiopyran
• 英文别名: 4-ethenyl-3-propan-2-yl-3,6-dihydro-2H-thiopyran
• CAS: 1374576-64-3
• 化学式: C₁₀H₁₆S
• 分子量: 168.303
• InChiKey: XNMBFGINGUIXOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-isopropyl-4-vinyl-3,6-dihydro-2H-thiopyran 在 Raney nickel 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 140.5h， 生成 (1R,4aS,10aS)-methyl-7-methoxy-1-methyl-2-((S)-3-methylbutan-2-yl)-1,4,4a,9,10,10a-hexahydrophenanthrene-4a-carboxylate
  参考文献：
  名称：

  使用硫使能的阴离子级联反应高效合成硫吡喃

  摘要：

  第五要素：开发了一种有效的新型合成方法，可在一锅中获得3,6-dihydro-2 H - thiopyrans 1。该方法采用阴离子级联，其通过将乙烯基亲核试剂加到羰基上，然后硫代磷酸酯从S到O的迁移和分子内硫醇盐的置换来触发。该范围适用于各种酮和酯底物。

  DOI：

  10.1002/anie.201108261
• 作为产物：
  描述：

  O,O-diethyl S-(3-hydroxy-2-isopropyl-3-vinylpent-4-en-1-yl) phosphorodithioate 在 potassium tert-butylate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.08h， 生成 3-isopropyl-4-vinyl-3,6-dihydro-2H-thiopyran
  参考文献：
  名称：

  使用硫使能的阴离子级联反应高效合成硫吡喃

  摘要：

  第五要素：开发了一种有效的新型合成方法，可在一锅中获得3,6-dihydro-2 H - thiopyrans 1。该方法采用阴离子级联，其通过将乙烯基亲核试剂加到羰基上，然后硫代磷酸酯从S到O的迁移和分子内硫醇盐的置换来触发。该范围适用于各种酮和酯底物。

  DOI：

  10.1002/anie.201108261

文献信息

• [EN] TRICYCLIC MOSQUITOCIDES AND METHODS OF MAKING AND USING THEREOF<br/>[FR] COMPOSÉS ANTIMOUSTIQUES TRICYCLIQUES ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：ARIZONA BOARD REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA

  公开号：WO2016007913A1

  公开（公告）日：2016-01-14

  Compounds that inhibit digestion in blood-ingesting pests are described herein. In one embodiment, the compounds described herein block entry of blood into the midgut and thereby inhibit digestion and nutrient processing. In another embodiment, the compounds described herein prevent pathogens contained in the blood meal from entering the midgut where they could cross the epithelial cell layer and infect the mosquito. The compounds can be administered to a population of blood-ingesting pests, such as mosquitos, directly or indirectly in an effective amount to prevent mosquitoes from transmitting diseases such as malaria, dengue fever, West Nile virus and lymphatic filariasis. Preferably, the compounds are lethal to blood-ingesting pests. The compounds can be combined with one or more excipients to prepare compositions.

  本文描述了抑制吸血害虫消化的化合物。在一种实施方式中，所述化合物阻止血液进入中肠，从而抑制消化和营养处理。在另一种实施方式中，所述化合物防止血液中含有的病原体进入中肠，病原体可能穿过上皮细胞层并感染蚊子。这些化合物可以直接或间接地以有效剂量施用于吸血害虫群体，如蚊子，以防止蚊子传播疾病，如疟疾、登革热、西尼罗河病毒和淋巴丝虫病。最好，这些化合物对吸血害虫具有致命作用。这些化合物可以与一个或多个赋形剂结合以制备组合物。
• Tricyclic mosquitocides and methods of making and using thereof
  申请人：The Arizona Board of Regents on Behalf of the University of Arizona

  公开号：US10370385B2

  公开（公告）日：2019-08-06

  Compounds that inhibit digestion in blood-ingesting pests are described herein. In one embodiment, the compounds described herein block entry of blood into the midgut and thereby inhibit digestion and nutrient processing. In another embodiment, the compounds described herein prevent pathogens contained in the blood meal from entering the midgut where they could cross the epithelial cell layer and infect the mosquito. The compounds can be administered to a population of blood-ingesting pests, such as mosquitos, directly or indirectly in an effective amount to prevent mosquitoes from transmitting diseases such as malaria, dengue fever, West Nile virus and lymphatic filariasis. Preferably, the compounds are lethal to blood-ingesting pests. The compounds can be combined with one or more excipients to prepare compositions.

  本文描述了抑制噬血害虫消化的化合物。在一个实施方案中，本文所述化合物可阻止血液进入中肠，从而抑制消化和营养加工。在另一个实施方案中，本文所述化合物可防止血餐中的病原体进入中肠，使其穿过上皮细胞层并感染蚊子。可以直接或间接地将有效量的化合物施用于噬血害虫（如蚊子）群体，以防止蚊子传播疾病，如疟疾、登革热、西尼罗河病毒和淋巴丝虫病。最好，这些化合物对嗜血害虫具有杀伤力。化合物可与一种或多种赋形剂结合制备组合物。
• TRICYCLIC MOSQUITOCIDES AND METHODS OF MAKING AND USING THEREOF
  申请人：The Arizona Board of Regents on Behalf of the University of Arizona

  公开号：US20170166580A1

  公开（公告）日：2017-06-15

  Compounds that inhibit digestion in blood-ingesting pests are described herein. In one embodiment, the compounds described herein block entry of blood into the midgut and thereby inhibit digestion and nutrient processing. In another embodiment, the compounds described herein prevent pathogens contained in the blood meal from entering the midgut where they could cross the epithelial cell layer and infect the mosquito. The compounds can be administered to a population of blood-ingesting pests, such as mosquitos, directly or indirectly in an effective amount to prevent mosquitoes from transmitting diseases such as malaria, dengue fever, West Nile virus and lymphatic filariasis. Preferably, the compounds are lethal to blood-ingesting pests. The compounds can be combined with one or more excipients to prepare compositions.
• Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade
  作者：Fang Li、David Calabrese、Matthew Brichacek、Ivy Lin、Jon T. Njardarson

  DOI：10.1002/anie.201108261

  日期：2012.2.20

  The fifth element: An efficient new synthetic method for accessing 3,6‐dihydro‐2H‐thiopyrans 1 in one pot has been developed. This method employs an anionic cascade, which is triggered by the addition of a vinyl nucleophile to a carbonyl group followed by S to O thiophosphate migration and an intramolecular thiolate displacement. The scope is demonstrated for a range of ketone and ester substrates

  第五要素：开发了一种有效的新型合成方法，可在一锅中获得3,6-dihydro-2 H - thiopyrans 1。该方法采用阴离子级联，其通过将乙烯基亲核试剂加到羰基上，然后硫代磷酸酯从S到O的迁移和分子内硫醇盐的置换来触发。该范围适用于各种酮和酯底物。