5-nonanethiol | 65225-61-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醇
• 英文名称: 5-nonanethiol
• 英文别名: nonane-5-thiol；5-Mercapto-nonan；Nonan-5-thiol
• CAS: 65225-61-8
• 化学式: C₉H₂₀S
• 分子量: 160.324
• InChiKey: JDWOQVKVHAKWNL-UHFFFAOYSA-N

物化性质

• 熔点：
  -44.55°C (estimate)
• 沸点：
  216.27°C (estimate)
• 密度：
  0.8491 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-nonanethiol 在 过氧乙酸 、 溶剂黄146 作用下， 反应 2.0h， 生成 5-nonanesulfonic acid
  参考文献：
  名称：

  Foldamers as Reactive Sieves:  Reactivity as a Probe of Conformational Flexibility

  摘要：

  A series of m-phenyleneethynylene (mPE) oligomers modified with a dimethylaminopyridine (DMAP) unit were treated with methyl sulfonates of varying sizes and shapes, and the relative reactivities were measured by UV spectrophotometry. Using a small-molecule DMAP analogue as a reference, each of the methyl sulfonates was shown to react at nearly identical rate. In great contrast, oligomers that are long enough to fold, and hence capable of binding the methyl sulfonate, experience rate enhancements of 18-1600-fold relative to that of the small-molecule analogue, depending on the type of alkyl chain attached to the guest. Three different oligomer lengths were studied, with the longest oligomers exhibiting the fastest rate and greatest substrate specificity. Even large, bulky guests show slightly enhanced methylation rates compared to that with the reference DMAP, which suggests a dynamic nature to the oligomer's binding cavity. Several mechanistic models to describe this behavior are discussed.

  DOI：

  10.1021/ja067670a
• 作为产物：
  描述：

  5-壬酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 1.5h， 生成 5-nonanethiol
  参考文献：
  名称：

  Foldamers as Reactive Sieves:  Reactivity as a Probe of Conformational Flexibility

  摘要：

  A series of m-phenyleneethynylene (mPE) oligomers modified with a dimethylaminopyridine (DMAP) unit were treated with methyl sulfonates of varying sizes and shapes, and the relative reactivities were measured by UV spectrophotometry. Using a small-molecule DMAP analogue as a reference, each of the methyl sulfonates was shown to react at nearly identical rate. In great contrast, oligomers that are long enough to fold, and hence capable of binding the methyl sulfonate, experience rate enhancements of 18-1600-fold relative to that of the small-molecule analogue, depending on the type of alkyl chain attached to the guest. Three different oligomer lengths were studied, with the longest oligomers exhibiting the fastest rate and greatest substrate specificity. Even large, bulky guests show slightly enhanced methylation rates compared to that with the reference DMAP, which suggests a dynamic nature to the oligomer's binding cavity. Several mechanistic models to describe this behavior are discussed.

  DOI：

  10.1021/ja067670a

文献信息

• 一种硫代甲苯二异(硫)氰酸酯的制备方法
  申请人：西安近代化学研究所

  公开号：CN111848476B

  公开（公告）日：2022-05-24

  本发明公开一种硫代甲苯二异(硫)氰酸酯的制备方法。所公开的方法采用硫醇为亲核试剂，在添加剂作用下将TNT转化为单硫代产物2S‑T1、4S‑T1或二者任意比例混合物；再以氢气为还原剂，在催化氢化条件下得到还原产物2S‑T2、4S‑T2或二者任意比例混合物；进一步经光气化得到目标甲苯二异(硫)氰酸酯2S‑T3、4S‑T3或二者任意比例混合物。本发明的制备方法具有清洁、高效的特点，产品甲苯二异(硫)氰酸酯在聚氨酯、聚碳酸酯等高分子领域具有广泛应用前景；该方法为废旧弹药中TNT的再利用提供技术支持。
• OXONIUM AND SULFONIUM SALTS
  申请人：Ignatyev Nikolai (Mykola)

  公开号：US20090036628A1

  公开（公告）日：2009-02-05

  The present invention relates to oxonium salts having [(R o ) 3 O] + cations and sulfonium salts having [(R o ) 3 S] + cations, where R o denotes straight-chain or branched alkyl groups having 1-8 C atoms or phenyl which is unsubstituted or substituted by R o , OR o , N(R o ) 2 , CN or halogen, and anions selected from the group of [PF x (C y F 2y+1−z H z ) 6−x ] − anions, where 2≦x≦5, 1≦y≦8 and 0≦z≦2y+1, or anions selected from the group of [BF n (CN) 4−n ] − anions, where n=0, 1 , 2 or 3, or anions selected from the group of [(R f1 SO 2 ) 2 N] − anions or anions selected from the group of [BF w R f2 4−w ] − anions, to processes for the preparation thereof, and to the use thereof, in particular for the preparation of ionic liquids.

  本发明涉及具有[(Ro)3O]+阳离子和[(Ro)3S]+阳离子的氧化铵盐和磺化铵盐，其中Ro表示直链或支链烷基基团，含有1-8个碳原子，或者未被Ro，ORo，N(Ro)2，CN或卤素取代的苯基，并且阴离子选自[PFx(CyF2y+1−zHz)6−x]−阴离子组，其中2≦x≦5，1≦y≦8，0≦z≦2y+1，或者选自[BFn(CN)4−n]−阴离子组，其中n=0, 1, 2或3，或者选自[(Rf1SO2)2N]−阴离子组或选自[BFwRf24−w]−阴离子组，以及其制备方法和用途，特别是用于制备离子液体。
• A high yielding, one-pot synthesis of S,S-dialkyl dithiocarbonates through the corresponding thiols using Mitsunobu’s reagent
  作者：A. K. Chaturvedi、D. Chaturvedi、N. Mishra、V. Mishra

  DOI：10.1007/bf03246060

  日期：2010.9

  A novel Mitsunobu-based technique has been developed for the synthesis of a variety of symmetrical and unsymmetrical S,S-dialkyl dithiocarbonates from various corresponding primary, secondary and tertiary thiols using gaseous carbon dioxide, in good to excellent yields.

  已经开发出一种新颖的基于Mitsunobu的技术，该技术使用气态二氧化碳从各种相应的伯，仲和叔硫醇合成多种对称和不对称的S，S-二烷基二硫代碳酸酯，产率高至优异。
• An efficient, one-pot synthesis of trithiocarbonates from the corresponding thiols using the Mitsunobu reagent
  作者：Devdutt Chaturvedi、Amit K. Chaturvedi、Nisha Mishra、Virendra Mishra

  DOI：10.1016/j.tetlet.2008.06.001

  日期：2008.8

  A novel Mitsunobu-based protocol has been developed for the synthesis of a variety of symmetrical and unsymmetrical trithiocarbonates from primary, secondary and tertiary thiols using carbon disulfide, in good to excellent yields. This protocol is mild and efficient compared to other reported methods.

  已经开发了一种新颖的基于Mitsunobu的方案，该方案可使用二硫化碳从伯，仲和叔硫醇合成多种对称和不对称的三硫代碳酸酯，收率良好。与其他报告的方法相比，该协议是温和有效的。
• An Efficient, One-Pot Synthesis of <i>S</i>-Alkyl Thiocarbamates from the Corresponding Thiols Using the Mitsunobu Reagent
  作者：Devdutt Chaturvedi、Nisha Mishra、Virendra Mishra

  DOI：10.1055/s-2008-1032025

  日期：2008.2

  A novel Mitsunobu-based protocol has been developed for the synthesis of variety of S-alkyl thiocarbamates from the corresponding thiols and amines using gaseous carbon dioxide, in good to excellent yields. This protocol is mild and efficient compared to other reported methods.

  一种新的基于Mitsunobu反应的协议已被开发，用于从相应的硫醇和胺合成多种S-烷基硫 carbamate，使用气态二氧化碳，产率良好至优异。与其他报告的方法相比，该协议温和且高效。