2-(氯甲基)-1,3-二噻戊环 | 86147-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 中文名称: 2-(氯甲基)-1,3-二噻戊环
• 英文名称: 2-(Chloromethyl)-1,3-dithiolane
• 英文别名: 2-chloromethyl-1,3-dithiolane
• CAS: 86147-22-0
• 化学式: C₄H₇ClS₂
• mdl: MFCD19233875
• 分子量: 154.685
• InChiKey: HZXIGTCQJZOQFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  245.2±15.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(氯甲基)-1,3-二噻戊环 在 盐酸 作用下， 73.0~79.0 ℃ 、700.01 Pa 条件下， 以57%的产率得到2,3-dihydro-1,4-dithiin
  参考文献：
  名称：

  杂环融合环烷倍半萜的立体选择性和模块化组装方法

  摘要：

  据报道，对于常见的环烷和异环烷倍半萜天然产物中发现的分子骨架，采用立体选择性合成方法。合成方法构成了对复杂的天然产物支架的可扩展，模块化以及不对称的通道，其中可以通过选择不同的起始原料来简单地调节取代模式和立体化学。该方法允许快速引入各种杂环亚结构，例如（苯并呋喃），（苯并）噻吩，二硫辛，噻唑和吲哚，它们实际上也促进并指导了关键的分子内环化步骤。

  DOI：

  10.1002/chem.201803248
• 作为产物：
  描述：

  2-氯乙醛缩二甲醇 、 1,2-乙二硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-(氯甲基)-1,3-二噻戊环
  参考文献：
  名称：

  未受保护的吲哚的脱环 (3 + 2) 环加成

  摘要：

  各种吲哚与二硫代烯丙基阳离子的 (3 + 2) 环加成反应提供了脱芳构化的环戊烷基加合物，具有完全控制区域选择性和优异的化学和非对映选择性。反应的成功关键依赖于使用过量的非常强的布朗斯台德酸，这自相矛盾地防止了碳正离子的副反应。该反应耐受敏感的官能团，如碱性胺或游离羟基，我们证明了它在高度官能化、未保护的吲哚的后期衍生化中的用途。

  DOI：

  10.1021/acs.orglett.2c01214

文献信息

• METHODS FOR PREPARATION OF (4,6-DIHALO-PYRIMIDIN-5-YL)-ACETALDEHYDES
  申请人：SUZHOU JONATHAN NEW MATERIAL TECHNOLOGY CO., LTD.

  公开号：US20150368206A1

  公开（公告）日：2015-12-24

  This invention relates to the synthesis of chemical compounds and particularly to methods for the preparation of (4,6-dihalo-pyrimidin-5-yl)-acetaldehydes. The methods involve preparing a compound of the following general formula V from a compound of the following general formula IV through hydrolysis under the action of mercury dichloride and calcium carbonate, according to the following equation: wherein X is Cl or Br. The methods offer the benefits of use of highly available materials, high step yields, moderate reaction conditions, simply post-processing and purification, and suitability to industrialized production.

  这项发明涉及化学化合物的合成，特别是关于制备（4,6-二卤嘧啶-5-基）-乙醛的方法。该方法涉及通过在汞二氯化物和碳酸钙的作用下，通过水解将以下一般式IV的化合物制备成以下一般式V的化合物，如下方程所示：其中X为Cl或Br。该方法具有使用易得材料、高步骤产率、适度的反应条件、简单的后处理和纯化，以及适合工业化生产等优点。
• Synthesis of 1,3-dithiolane-containing nitromethene compounds and their biological activity as insecticides
  作者：Dongmei Li、Zhongzhen Tian、Zhiping Xu、Gaolei Wang

  DOI：10.1007/s11164-012-0737-0

  日期：2013.5

  1,3-Dithiolane-containing nitromethylene derivatives, as candidates for screening as neonicotinoid insecticides, were synthesized by reaction of compound (4) with 1,2-ethanedithiol. Compounds 7a–g were obtained via Mannich reaction of (E)-1-((1,3-dithiolan-2-yl)methyl)-2-(nitromethylene)imidazolidine (6), primary amines and formaldehyde. The synthesized compounds were identified by 1H NMR, IR spectroscopy and elemental analysis. Preliminary bioassays indicated that most of the compounds had moderate insecticidal activity against Aphis craccivora. The relationship between molecular structure and biological activity is discussed.

  通过化合物(4)与1,2-乙二硫醇反应合成了含1,3-二硫戊环的硝基亚甲基衍生物，作为筛选新烟碱类杀虫剂的候选物。化合物7a–g是通过(E)-1-((1,3-二硫杂环戊烷-2-基)甲基)-2-(硝基亚甲基)咪唑烷(6)、伯胺和甲醛的曼尼希反应获得的。合成的化合物通过1H NMR、IR光谱和元素分析进行​​鉴定。初步生物测定表明，大多数化合物对蚜虫具有中等的杀虫活性。讨论了分子结构与生物活性之间的关系。
• A short and efficient synthesis of ketene O,O- and S,S-acetals under focused microwave irradiation and solvent-free conditions
  作者：Angel Díaz-Ortiz、Pilar Prieto、André Loupy、David Abenhaïm

  DOI：10.1016/0040-4039(96)00110-4

  日期：1996.3

  A new methodology leading to ketene O,O- and S,S-acetals is reported. The title compounds were prepared from the corresponding halogenated precursors under microwave irradiation in the absence of solvent within 5–25 minutes with excellent yields. Yields obtained under microwaves are by far the best when compared to those obtained by ultrasound or classical heating in the same conditions of time and

  报道了导致烯酮O，O-和S，S-乙缩醛的新方法。标题化合物是由相应的卤代前体在无溶剂下于5-25分钟内在微波辐射下制备的，具有优异的收率。与在相同的时间和温度条件下通过超声或经典加热获得的产率相比，在微波下获得的产率迄今为止是最好的。
• Exploratory Synthetic Studies Involving the Tricyclo[9.3.0.02,8]tetradecane Ring System Peculiar to the Cyathins
  作者：Karl R. Dahnke、Leo A. Paquette

  DOI：10.1021/jo00083a034

  日期：1994.2

  Following an improved preparation of 2-methylene-1,3-dithiolane, this ketene acetal was shown to undergo inverse-electron-demand Diels-Alder cycloaddition to tropone. Regiocontrolled copper hydride reduction and resolution via sulfoximine adducts was readily achieved to give (-)-9. Addition to 9 of the chiral nonracemic vinyl bromides 21 and 22 proceeded with endo capture of the nucleophilic vinyllithium to give carbinols that underwent anionic oxy-Cope rearrangement at somewhat elevated temperatures. The [3,3] sigmatropic event delivered cis,syn,cis-tricyclo[9.3.0.0(2,8)]tetradecnones possessing structural frameworks related to the cyathins. Once 31 was in hand, it proved an easy matter to introduce added unsaturation and oxygen substituents. The tendency of certain derivatives for transannular cyclization was made quite apparent. Attempts to introduce a C(6)-alpha-methyl substituent was not achieved, chiefly as the result of the overall molecular concavity of this class of intermediates. A variety of reactions aimed at enhancing the level of functionality in rings B and C was explored and processes conducive to the attainment of these goals were developed.
• 2-METHYLENE-1,3-DITHIOLANE
  作者：Dahnke, Karl R.、Paquette, Leo A.

  DOI：10.15227/orgsyn.071.0175

  日期：——