N-(hexanethio)succinimide | 1360548-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(hexanethio)succinimide
• 英文别名: N-(hexylthio)succinimide；1-Hexylsulfanylpyrrolidine-2,5-dione；1-hexylsulfanylpyrrolidine-2,5-dione
• CAS: 1360548-31-7
• 化学式: C₁₀H₁₇NO₂S
• 分子量: 215.316
• InChiKey: BURNLRFPKNWUDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  316.4±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(hexanethio)succinimide 在 重水 、 溶剂黄146 作用下， 以 二氯甲烷-D2 为溶剂， 反应 4.0h， 生成 S-hexyl hexane-1-sulfinothioate
  参考文献：
  名称：

  New Class of Biodegradable Polymers Formed from Reactions of an Inorganic Functional Group

  摘要：

  Although numerous small molecules have been synthesized with sulfenamide bonds (R2N-SR), this is the first report of the synthesis of polysulfenamides. These polymers are readily synthesized at room temperature using secondary diamines and dithiosuccinimides. The dithiosuccinimides were readily synthesized in one step by the reaction of dithiols such as HS(CH2)(6)SH with N-chlorosuccinimide. The resulting dithiosuccinimides were either recrystallized or readily purified by chromatography on silica gel and required no special handling. The conversions of polymerization ranged from 95 to 98%, and the molecular weights of the polymer reached as high as 6300 g mol(-1). The sulfenamide bond was very stable in organic solvents, and no degradation was observed under atmospheric conditions in C6D6 for 30 days. In contrast, the sulfenamide bond readily decomposed in less than 12 h in D2O. Polysulfenamides were fabricated into micrometer-sized particles loaded with dye and endocytosed into JAWSII immature dendritic and HEK293 cells. Polysulfenamides represent a new class of polymers that are readily synthesized, stable in aprotic solvents, and readily degrade in water.

  DOI：

  10.1021/ma300190b
• 作为产物：
  描述：

  N-氯代丁二酰亚胺 、 1-己硫醇 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 N-(hexanethio)succinimide
  参考文献：
  名称：

  艾伦烯的催化亲电硫代碳环化

  摘要：

  公开了一种通过丙二烯的催化亲电硫代碳环化来构建具有优异区域选择性的茚基硫化物的有效方法。反应在低温下通过硒化物催化在 TMSOTf 存在下进行。在这些条件下，不仅亲电的芳硫基试剂而且亲电的烷硫基试剂都能很好地工作。此外，该方法可应用于丙二烯的分子间叠氮硫基化反应。

  DOI：

  10.1021/acs.orglett.1c03270

文献信息

• Enantioselective Construction of Chiral Sulfides via Catalytic Electrophilic Azidothiolation and Oxythiolation of <i>N</i>-Allyl Sulfonamides
  作者：Yaoyu Liang、Xiaodan Zhao

  DOI：10.1021/acscatal.9b01900

  日期：2019.8.2

  An efficient and convenient pathway was developed for enantioselective synthesis of chiral sulfides by chiral bifunctional selenide-catalyzed electrophilic azidothiolation and oxythiolation of N-allyl sulfonamides. By this protocol, a variety of chiral vicinal azidosulfides and oxysulfides were obtained in good yields with high enantioselectivities and diastereoselectivities. In this transformation

  通过手性双官能亚硒酸酯催化的亲电子叠氮基硫代化和N-烯丙基磺酰胺的氧硫代化，开发了一种高效，便捷的手性硫化物的对映选择性合成方法。通过该方案，以高收率获得了具有高对映选择性和非对映选择性的各种手性邻位叠氮基硫化物和氧硫化物。在该转化中，不仅亲电芳基硫醇化试剂而且各种各样的亲电烷基硫醇化试剂都非常有效。通过将产物进一步转化为多样化的化合物，阐明了该方法的实际应用。
• Catalyst-Free Isothiocyanatoalkylthiation of Styrenes with (Alkylthio)pyrrolidine-2,5-diones and Trimethylsilyl Isothiocyanate
  作者：Hua Tian、Jipan Yu、Haijun Yang、Changjin Zhu、Hua Fu

  DOI：10.1002/adsc.201501181

  日期：2016.6.2

  A simple and efficient catalyst‐free method for isothiocyanatoalkylthiation of styrenes has been developed. The protocol uses (alkylthio)pyrrolidine‐2,5‐diones and trimethylsilyl isothiocyanate as the isothiocyanatoalkylthiolating reagents, dimethylformamide (DMF) as the solvent, and the reactions were completed within one hour with tolerance of some functional groups. No catalyst and additive were

  已经开发出一种简单高效的无催化剂的苯乙烯异硫氰酸根合烷基化方法。该方案使用（烷硫基）吡咯烷-2,5-二酮和异硫氰酸三甲基硅烷基酯作为异硫氰酸根合烷基硫醇化试剂，二甲基甲酰胺（DMF）作为溶剂，反应在1小时内完成，且具有一定的官能团耐受性。在反应体系中不需要催化剂和添加剂，避免了目标产物中过渡金属催化剂的任何污染。因此，本方法为通过硫化物和异硫氰酸酯的组合合成化合物提供了方便，有效和实用的策略。
• Biodegradable Polymers with Sulfenamide Bonds for Drug Delivery Applications
  申请人：Bowden Ned B.

  公开号：US20140099506A1

  公开（公告）日：2014-04-10

  The present invention provides polysulfenamides and methods of making same.

  本发明提供了聚硫胺酰胺及其制备方法。
• 一类手性邻氨基硫醚化合物及其制备方法
  申请人：中山大学

  公开号：CN110283108B

  公开（公告）日：2021-07-20

  本发明公开了一类手性邻氨基硫醚化合物及其制备方法。该方法利用不对称催化烯烃双官能化的方法快速高效合成具有高对映选择性、高区域选择性以及高产率的手性邻氨基硫醚化合物。该方法适用于合成烷基硫醚和芳基硫醚，能兼容多种官能团。本发明操作简单，步骤简短等优点为合成各种手性邻氨基硫醚化合物奠定了基础。
• A1 adenosine receptor antagonists
  申请人：Wilson N. Constance

  公开号：US20050187226A1

  公开（公告）日：2005-08-25

  The present invention provides novel adenosine receptor antagonists, more particularly, A 1 adenosine receptor antagonists. Pharmaceutical compositions comprising an A 1 adenosine receptor antagonist disclosed herein and a pharmaceutically acceptable carrier are further provided. Compositions also include diagnostic assay-type probes comprising a novel A 1 adenosine receptor antagonist that is labeled or conjugated with radioactive or non-radioactive material. Methods for treating A 1 adenosine receptor related disorders comprising administering an A 1 adenosine receptor antagonist of the invention are also disclosed. The novel A 1 adenosine receptor antagonist compositions find further use in diagnostic and imaging methods.

  本发明提供了新型腺苷受体拮抗剂，特别是A1腺苷受体拮抗剂。此外，还提供包含本文所披露的A1腺苷受体拮抗剂和药学上可接受的载体的制药组合物。组合物还包括诊断检测型探针，其中包含一种新型A1腺苷受体拮抗剂，该拮抗剂被标记或与放射性或非放射性物质结合。本发明还披露了通过给予本发明的A1腺苷受体拮抗剂来治疗A1腺苷受体相关疾病的方法。新型A1腺苷受体拮抗剂组合物还可用于诊断和成像方法。