S-dodecyl hexanethioate | 1607799-57-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-dodecyl hexanethioate
• CAS: 1607799-57-4
• 化学式: C₁₈H₃₆OS
• 分子量: 300.549
• InChiKey: MPBAGQAASNAELM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-dodecyl hexanethioate 在 1-[(S)-3-benzyl-1-diethylamino-4-phenyl-3-trimethylsiloxybutan-2-yl]-3-(3,5-bistrifluoromethylphenyl)thiourea 、 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 S-dodecyl (E)-2-(tert-butyldimethylsiloxymethylene)hexanethioate
  参考文献：
  名称：

  2-甲酰基（硫）酯对乙烯基酮的有机催化1,4加成反应：有效获得具有季碳立体中心的无环手性结构单元

  摘要：

  2-甲酰基（硫代）酯被用作亲核试剂，以获得难以接近的无环手性结构单元，该单元在季碳原子上带有多功能官能团，可以将乙烯基对映体选择性地进行1,4加成。为了在当前的1,4加成反应中实现高对映选择性，开发了含有庞大手性骨架的硫脲叔胺作为催化剂，并对产物进行了几次衍生化反应以证明产物的合成用途。

  DOI：

  10.1002/chem.201504479
• 作为产物：
  描述：

  正己醛 、 十二硫醇 在 iron(II) bromide 、 叔丁醇 作用下， 以 水 为溶剂， 反应 1.0h， 以63%的产率得到S-dodecyl hexanethioate
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of Thioesters from Thiols and Aldehydes in Water

  摘要：

  The preparation of thioesters through the iron-catalyzed coupling reaction of thiols with aldehydes is described. The reactions were carried out by using tert-butyl hydroperoxide (TBHP) as an oxidant and water as a solvent in most cases. This system is compatible with a variety of functional groups.

  DOI：

  10.1021/jo500574p

文献信息

• Tunable Aryl Imidazolium Recyclable Ionic Liquid with Dual Brønsted–Lewis Acid as Green Catalyst for Friedel–Crafts Acylation and Thioesterification
  作者：Yi-Jyun Lin、Yao-Peng Wu、Mayur Thul、Ming-Wei Hung、Shih-Huan Chou、Wen-Tin Chen、Wesley Lin、Michelle Lin、Daggula Mallikarjuna Reddy、Hsin-Ru Wu、Wen-Yueh Ho、Shun-Yuan Luo

  DOI：10.3390/molecules25020352

  日期：——

  Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel–Crafts acylation and thioesterification in sealed tubes. These reactions can form a C−C bond and a C−S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.

  独特可调节的芳基咪唑离子液体成功地催化了密封管中的Friedel-Crafts酰化和硫酯化反应。这些反应可以以高原子经济性形成C−C键和C−S键。离子液体表现出高活性，催化了必要的反应，产率良好至优良，同时保持其催化活性以进行循环利用。
• [EN] AMINO LIPIDS, THEIR SYNTHESIS AND USES THEREOF<br/>[FR] LIPIDES AMINÉS, LEUR SYNTHÈSE ET LEURS UTILISATIONS
  申请人：KARLSRUHER INST TECHNOLOGIE

  公开号：WO2012167869A1

  公开（公告）日：2012-12-13

  The present invention provides new amino lipids and a convenient method for synthesising these compounds. These (cationic) amino lipids have good properties as transfection agents. The method is an economic versatile two step synthesis allowing the preparation of various amino lipids thus leading to the assembly of a combinatorial library of transfection agents. Moreover, the present invention provides lipid particles (liposomes) containing said amino lipids and their use for delivering bioactive agents into cells. The invention encompasses also the use of lipid particles containing the cationic amino lipids as medicament.

  本发明提供了新的氨基脂质和一种方便的合成这些化合物的方法。这些（阳离子）氨基脂质作为转染剂具有良好的性能。该方法是一种经济多功能的两步合成方法，允许制备各种氨基脂质，从而导致转染剂组合库的组装。此外，本发明提供了含有上述氨基脂质的脂质粒子（脂质体）及其用于将生物活性剂输送到细胞中的用途。该发明还包括含有阳离子氨基脂质的脂质粒子作为药物的用途。
• Iron-Catalyzed Synthesis of Thioesters from Thiols and Aldehydes in Water
  作者：Yu-Ting Huang、Shao-Yi Lu、Chih-Lun Yi、Chin-Fa Lee

  DOI：10.1021/jo500574p

  日期：2014.5.16

  The preparation of thioesters through the iron-catalyzed coupling reaction of thiols with aldehydes is described. The reactions were carried out by using tert-butyl hydroperoxide (TBHP) as an oxidant and water as a solvent in most cases. This system is compatible with a variety of functional groups.
• Organocatalytic 1,4‐Addition Reaction of 2‐Formyl(thio)esters to Vinylketones: An Efficient Access to Acyclic Chiral Building Blocks with a Quaternary Carbon Stereocenter
  作者：Toshifumi Tatsumi、Tomonori Misaki、Takashi Sugimura

  DOI：10.1002/chem.201504479

  日期：2015.12.21

  2‐Formyl(thio)esters were utilized as pronucleophiles to obtain less‐accessible acyclic chiral building blocks bearing versatile functional groups on a quaternary carbon atom for enantioselective 1,4‐addition to vinylketones. To achieve high enantioselectivity in the present 1,4‐addition reaction, thiourea‐tertiary amines containing a bulky chiral backbone were developed as catalysts, and several derivatizations

  2-甲酰基（硫代）酯被用作亲核试剂，以获得难以接近的无环手性结构单元，该单元在季碳原子上带有多功能官能团，可以将乙烯基对映体选择性地进行1,4加成。为了在当前的1,4加成反应中实现高对映选择性，开发了含有庞大手性骨架的硫脲叔胺作为催化剂，并对产物进行了几次衍生化反应以证明产物的合成用途。