3-(benzylthio)propylamine | 23909-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(benzylthio)propylamine
• 英文别名: 3-benzylmercaptopropylamine；3-(Benzylthio)-1-propanamine；3-benzylsulfanylpropan-1-amine
• CAS: 23909-16-2
• 化学式: C₁₀H₁₅NS
• mdl: MFCD09936479
• 分子量: 181.302
• InChiKey: BPPMAWGRHJLFQK-UHFFFAOYSA-N

物化性质

• 沸点：
  98 °C(Press: 0.05 Torr)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  3-(benzylthio)propylamine 生成 4-nitro-benzoic acid-(3-benzylsulfanyl-propylamide)
  参考文献：
  名称：

  Studies on Thioesters Related to Coenzyme A. A Kinetic Study of Aminolysis and Hydrolysis of β-(N-Methylacetamino)-ethyl Thioacetate, N,S-Diacetylaletheine and γ-Acetaminopropyl Thioacetate¹

  摘要：

  DOI：

  10.1021/ja01593a023
• 作为产物：
  描述：

  3-苄基硫代丙腈 在 lithium aluminium tetrahydride 作用下， 生成 3-(benzylthio)propylamine
  参考文献：
  名称：

  The Synthesis of 5'-Deoxy-5'-S-(3-methylthiopropylamine)sulfoniumadenosine (“Decarboxylated S-Adenosylmethionine”)

  摘要：

  DOI：

  10.1021/jo01044a061

文献信息

• Building units for N-backbone cyclic peptides. Part 4.1 Synthesis of protected Nα-functionalized alkyl amino acids by reductive alkylation of natural amino acids
  作者：Gal Bitan、Dan Muller、Ron Kasher、Evgenia V. Gluhov、Chaim Gilon

  DOI：10.1039/a608389g

  日期：——

  A new method for the synthesis of protected Nα-(ω-Y-alkyl) amino acids (Y is a thio, amino or carboxy group) and related compounds by reductive alkylation of natural amino acids is reported. These new amino acids serve as building units for the synthesis of backbone-cyclic peptides. They are orthogonally protected at the α-amino position by butoxycarbonyl (Boc) or 9-fluorenylmethoxycarbonyl (Fmoc), using trimethylsilyl temporary protection, to allow for their incorporation into peptides by solid phase peptide synthesis.

  报道了一种通过天然氨基酸的还原烷基化合成保护的Nα-(γ-Y-烷基)氨基酸(Y为硫、氨基或羧基基团)及相关化合物的新方法。这些新型氨基酸作为合成骨架环肽的构建单元，在α-氨基位置通过叔丁氧羰基(Boc)或9-芴甲氧羰基(Fmoc)进行正交保护，并使用三甲基硅烷临时保护，以便通过固相肽合成法将其并入肽链中。
• Synthesis and biochemical properties of chemically stable product analogs of the reaction catalyzed by S-adenosyl-L-methionine decarboxylase
  作者：Michael Kolb、Charles Danzin、Jacqueline Barth、Nicole Claverie

  DOI：10.1021/jm00347a014

  日期：1982.5

  Structural analogues of decarboxylated S-adenosyl-L-methionine (dc-SAM), product of the reaction catalyzed by S-adenosyl-L-methionine decarboxylase (SAM-DC), with modifications in the side-chain portion of the molecule have been synthesized, and their ability to inhibit SAM-DC has been investigated. Mainly, compounds with a nitrogen atom in place of the sulfur were investigated. The data from these

  脱羧化S-腺苷-L-蛋氨酸（dc-SAM）的结构类似物，它是由S-腺苷-L-蛋氨酸脱羧酶（SAM-DC）催化的反应产物，在分子的侧链部分有修饰合成，并研究了其抑制SAM-DC的能力。主要研究了用氮原子代替硫的化合物。这些抑制研究的数据导致了对结合到SAM-DC上所需的结构特征的描绘。结论是，末端伯氨基，末端羧基和the官能度对于在SAM-DC上结合不是必需的。还发现dc-SAM的类似物仍能与该酶形成偶氮甲碱，其中用氮代替硫是唯一的修饰。
• Enantioselective Synthesis of <i>N</i> ,<i>S</i> -Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis
  作者：Souvagya Biswas、Koji Kubota、Manuel Orlandi、Mathias Turberg、Dillon H. Miles、Matthew S. Sigman、F. Dean Toste

  DOI：10.1002/anie.201711277

  日期：2018.1.8

  Deuterium‐labelling experiments were performed to identify the stereodiscrimination step of this process. Further analysis of the reaction transition states, by means of multidimensional correlations and DFT calculations, highlight the existence of a set of weak noncovalent interactions between the catalyst and substrate that govern the enantioselectivity of the reaction.

  据报道，这是首次使用相转移催化的对映体选择性氧化氧化Pummerer型转化，以提供对映体富集的含硫杂环。该反应包括将硫化物直接氧化成硫鎓中间体，然后进行不对称分子内亲核加成反应，形成具有中等至高对映体选择性的手性环状N，S-缩醛。进行氘标记实验以鉴定该过程的立体鉴别步骤。通过多维相关和DFT计算对反应过渡态进行进一步分析，突出了催化剂与底物之间存在一组弱的非共价相互作用，这些相互作用决定了反应的对映选择性。
• Dimethyl tyrosyl amide sulfides, sulfoxides and sulfones
  申请人：G.D. Searle & Co.

  公开号：EP0361482A1

  公开（公告）日：1990-04-04

  Dimethyl tyrosyl amide sulfides, sulfoxides and sulfones that are useful as opioid analgesics.

  可用作阿片类镇痛剂的二甲基酪氨酰硫化物、硫醚和砜。
• Copper(I) complexes of N-centered aliphatic tripodal trithioether ligands – Adjustment of complex geometry by variation of spacer lengths
  作者：Marc Blomenkemper、Henning Schröder、Tania Pape、F. Ekkehardt Hahn

  DOI：10.1016/j.ica.2010.10.008

  日期：2011.1

  A series of novel aliphatic tripodal trithioether ligands 4-6 differing in the lengths of the alkyl chains between central nitrogen atom and sulfur donor function has been synthesized. The neutral ligands 4-6 react with copper(I) under formation of the mononuclear complexes 7-9 featuring exclusive coordination of the metal center by the tertiary amine and the three thioether donor functions of the tripodal ligand. Molecular structures of 7 and 9 show a direct influence of the spacer lengths between central and terminal donor functions on the geometry of the tetracoordinated complex cations. Substitution of one ethylene by a propylene spacer leads to a larger bite angle between the amine and thioether donor functions and effects a tetrahedral distortion for the complex cation in 7. For the copper(I) compound 9 with a ligand possessing exclusively propylene spacers this effect is increased leading to a tetrahedral geometry of the complex cation. (C) 2010 Elsevier B.V. All rights reserved.