4-thioisobutyrylmorpholine | 97856-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-thioisobutyrylmorpholine
• 英文别名: 4-thioisobutyryl-morpholine；Thioisobutyrmorpholid；2-Methyl-1-morpholin-4-ylpropane-1-thione
• CAS: 97856-41-2
• 化学式: C₈H₁₅NOS
• 分子量: 173.279
• InChiKey: KJUXBAKIRGSUAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-thioisobutyrylmorpholine 在 sodium azide 、 copper(l) cyanide 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 25.0h， 生成 2-methyl-N-methylsulfanyl-1-morpholin-4-ylpropan-1-imine
  参考文献：
  名称：

  Stansfield, Frank, Journal of the Chemical Society. Perkin transactions I, 1984, # 12, p. 2933 - 2935

  摘要：

  DOI：
• 作为产物：
  描述：

  吗啉 、 (E)-2-methyl-1-methylthio-1-sulfinylpropane 以 二氯甲烷 为溶剂， 反应 24.0h， 以25%的产率得到4-thioisobutyrylmorpholine
  参考文献：
  名称：

  Carbon versus sulfur addition of nucleophiles to sulfines: The case of amines

  摘要：

  Reaction of dithioester sulfines 4 with amines leads to thioamides 5. Sulfine 7, obtained from (-)-thiocamphor, reacts with primary amines at room temperature to afford chiral imines 8. Carbophilic addition, instead of thiophilic addition, has thus been evidenced.

  DOI：

  10.1016/s0040-4039(00)61689-1

文献信息

• A New Versatile One-Pot Synthesis of Functionalized Thioamides From Grignards, Carbon Disulfide and Amines
  作者：Alan R. Katritzky、Jean-Luc Moutou、Zhijun Yang

  DOI：10.1055/s-1995-4144

  日期：1995.12

  The one-pot successive reactions of Grignard reagents with carbon disulfide and amines mediated by 1-trifluoromethylsulfonylbenzotriazole or triflic anhydride, provide and attractive and general route to thioamides. A wide variety of amines (primary alkyl, arylalkyl, secondary alkyl, cyclic amines, aniline, N-substituted anilines, heterocyclic amidines, amino alcohols, amino ethers, amino acetals, amino ketones, amino esters, amino amides (peptides), aminoalkenes, and diamines) and Grignard (primary alkyl, arylalkyl, aryl, secondary alkyl and tertiary alkyl) can be used, and thioamides are generally formed in good to moderate yields.

  由1-三氟甲磺酰苯并三唑或三氟甲磺酸酐介导的Grignard试剂与二硫化碳和胺的一锅连续反应提供了一条吸引人的、通用的硫酰胺合成途径。广泛种类的胺（一级烷基、芳基烷基、二级烷基、环状胺、苯胺、N-取代苯胺、杂环脒、氨基醇、氨基醚、氨基缩醛、氨基酮、氨基酯、氨基酰胺（肽）、氨基烯烃和二胺）以及Grignard试剂（一级烷基、芳基烷基、芳基、二级烷基和三级烷基）均可使用，并且通常以良好至中等的产率形成硫酰胺。
• PROTECTED MONOMER AND METHOD OF FINAL DEPROTECTION FOR RNA SYNTHESIS
  申请人：Dellinger Douglas J.

  公开号：US20100076183A1

  公开（公告）日：2010-03-25

  A nucleoside monomer that is protected by a thionocarbamate protecting group is provided, as well as a method for making a polynucleotide that uses the same. Also provided is a polynucleotide synthesis method that employs a diamine to deprotect a protected polynucleotide.

  提供了一种由硫代氨基甲酸酯保护基保护的核苷单体，以及使用该核苷单体制备多核苷酸的方法。还提供了一种利用二胺去保护受保护多核苷酸的多核苷酸合成方法。
• Transition‐Metal‐Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
  作者：Hao Jin、Xinzhi Chen、Chao Qian、Xin Ge、Shaodong Zhou

  DOI：10.1002/ejoc.202100588

  日期：2021.6.21

  A general method for one-pot synthesis of thioamides without transition metals or external oxidants is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Both alkyl and aryl thioamides could be obtained in moderate to excellent yields through this protocol. A high tolerance regarding various substituents on chlorohydrocarbon or amide was justified

  通过涉及氯代烃、酰胺和元素硫的三组分反应开发了一种无需过渡金属或外部氧化剂的一锅法合成硫代酰胺的通用方法。通过该协议，可以以中等至极好的收率获得烷基和芳基硫代酰胺。对氯代烃或酰胺上的各种取代基的高耐受性是合理的。值得注意的是，该协议不需要过渡金属或外部氧化剂。此外，还结合控制实验和量子化学计算对反应机制进行了研究。
• General Construction of Thioamides under Mild Conditions: A Stepwise Proton Transfer Process Mediated by EDTA
  作者：Hao Jin、Xin Ge、Shaodong Zhou

  DOI：10.1002/ejoc.202101013

  日期：2021.11.25

  of experiments and quantum chemical calculations. Ester, amide, and elemental sulfur are employed as the starting materials and ethylene diamine tetraacetic acid (EDTA) serves as the catalyst to facilitate the benign reaction. The catalytic role of EDTA is attributed to a stepwise proton transfer process in which EDTA transports a proton from the benzyl carbon to a sulfur atom.

  结合实验和量子化学计算，研究了一种通用、清洁和有效的硫代酰胺一锅合成方案。酯、酰胺和元素硫用作起始原料，乙二胺四乙酸 (EDTA) 作为催化剂以促进良性反应。EDTA 的催化作用归因于逐步质子转移过程，其中 EDTA 将质子从苄基碳转移到硫原子。
• Protected monomer and method of final deprotection for RNA synthesis
  申请人：Agilent Technologies, Inc.

  公开号：US10597421B2

  公开（公告）日：2020-03-24

  A method of deprotecting a solid support bound polynucleotide comprising at least one 2′-protected ribonucleotide in which a step of contacting the polynucleotide with a composition comprising a diamine is performed under conditions sufficient to deprotect and cleave the polynucleotide which remains retained on the solid support.

  一种对包含至少一种 2′-保护的核糖核苷酸的固体支持物结合的多核苷酸进行脱保护的方法，其中将多核苷酸与包含二胺的组合物接触的步骤是在足以对保留在固体支持物上的多核苷酸进行脱保护和裂解的条件下进行的。