2-[(4-甲基苄基)硫基]苯胺 | 136620-24-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-[(4-甲基苄基)硫基]苯胺
• 英文名称: 2-(p-tolylmethylsulfanyl)aniline
• 英文别名: 2-(4-methylbenzyl)thioaniline；2-(4-methylbenzyl)thioaniline(Man-4-MBzl)；2-[(4-Methylbenzyl)sulfanyl]aniline；2-[(4-methylphenyl)methylsulfanyl]aniline
• CAS: 136620-24-1
• 化学式: C₁₄H₁₅NS
• mdl: MFCD02152603
• 分子量: 229.346
• InChiKey: MVJABYMVHVSANO-UHFFFAOYSA-N

物化性质

• 沸点：
  371.3±30.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(4-甲基苄基)硫基]苯胺 在 溴 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 45.0h， 生成 1-isothiocyanato-2-[(4-methylphenyl)methylsulfanyl]benzene
  参考文献：
  名称：

  Synthesis of 2-Substituted 2,3-Dihydro-1,4-benzothiazine-3-thiones via Iminophosphoranes

  摘要：

  2-(Substituted methylsulfanyl)anilines (5) were treated with triphenylphosphine dibromide to yield iminophosphoranes (6), whose aza-Wittig reaction with carbon disulfide gave 2-(substituted methylsulfanyl)phenyl isothiocyanates(8). Cyclization of 8 by strong bases afforded 2-substituted 2,3-dihydro-1,4-benzothiazine-3-thiones (10).

  DOI：

  10.3987/com-95-7171
• 作为产物：
  描述：

  邻硝基苯硫酚 在 sodium ethanolate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.0h， 生成 2-[(4-甲基苄基)硫基]苯胺
  参考文献：
  名称：

  A New Synthetic Route to 1,5-Benzothiazepines. Synthesis of Derivatives of Diltiazem.

  摘要：

  通过硫稳定苄基阴离子和酯羰基的碳-碳环闭合，然后立体选择性还原 1，5-苯并硫氮杂卓二酮的 C3-羰基，从草酸盐（6）合成了多种地尔硫卓衍生物（9a-c）（7）。

  DOI：

  10.1248/cpb.40.1986

文献信息

• Cyclic anti-aggregatory peptides
  申请人：SmithKline Beecham Corporation

  公开号：US05643872A1

  公开（公告）日：1997-07-01

  This invention relates to compounds of the formula: ##STR1## wherein: A' is absent, Asn, Gln, Ala or Abu; A is absent or a D- or L-amino acid chosen from Arg, HArg, (Me.sub.2)Arg, (Et.sub.2)Arg, Abu, Ala, Gly, His, Lys, or an .alpha.-R' substituted derivative thereof, Dtc, Tpr and Pro; B is a D- or L-amino acid chosen from Arg, HArg, NArg, (Me.sub.2)Arg, (Et.sub.2)Arg and Lys or an .alpha.-R' substituted derivative thereof; Q is absent or a D or L amino acid chosen from Tyr, (Alk)Tyr, Phe, (4'W)Phe, HPhe, Phg, Pro, Trp, His, Ser, (Alk)Ser, Thr, (Alk)Thr, (Alk)Cys, (Alk)Pen, Ala, Val, Nva, Met, Leu, Ile, Nle and Nal, or an .alpha.-R' substituted derivative thereof; M is absent or Gly or a D- or L-amino acid chosen from Glu, Phe, Pro, Lys and Ser or, provided n is 1, B-Gly-Glu-Q; W is halogen or Alk; R' is Alk or PhCH.sub.2 ; ##STR2## wherein Z.sub.1 and Z.sub.2 are linked via a covalent bond between L.sup.1 and L.sup.2 ; or Z.sub.1 and Z.sub.2 are, taken together, a covalent bond between the amino terminal residue and the carboxy terminal residue; L.sup.1 and L.sup.2 are --S-- or --(CH.sub.2).sub.p --; X is R.sub.4 R.sub.5 N or H; Y is H, CONR.sub.1 R.sub.2 or CO.sub.2 R.sub.2 ; R.sub.1 and R.sub.2 are H, Alk or (CH.sub.2).sub.p Ar; R.sub.3 and R.sub.3' are H, Alk, (CH.sub.2).sub.p Ar or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.4 is H or Alk; R.sub.5 is R.sub.11, R.sub.11 CO, R.sub.11 OCO, R.sub.11 OCH(R.sub.11')CO, R.sub.11 NHCH(R.sub.11')CO, R.sub.11 SCH(R.sub.11')CO, R.sub.11 SO.sub.2 or R.sub.11 SO; R.sub.6 is Alk, OAlk, halogen or X; R.sub.7 is H, Alk, OAlk, halogen or Y; R.sub.8 and R.sub.8' are H, Alk, (CH.sub.2).sub.p Ph, (CH.sub.2).sub.p Nph or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.9 is H, Alk or Y; R.sub.10 is H or Alk; R.sub.11 and R.sub.11' are H, C.sub.1-5 alkyl, C.sub.3-7 cycloalkyl, Ar, Ar--C.sub.1-5 alkyl, Ar--C.sub.3-7 cycloalkyl; Ar is phenyl or phenyl substituted by one or two C.sub.1-5 alkyl, trifluoromethyl, hydroxy, C.sub.1-5 alkoxy or halogen groups; n is 1 or 2; q is 0 or 1; and p is 0, 1, 2 or 3; or a pharmaceutically acceptable salt thereof; which are effective for inhibiting platelet aggregation, pharmaceutical compositions for effecting such activity, a method for inhibiting platelet aggregation and clot formation in a mammal, and a method for inhibiting reocclusion of a blood vessel following fibrinolytic therapy.

  这项发明涉及以下式的化合物：##STR1## 其中：A'为不存在，Asn，Gln，Ala或Abu；A不存在或为Arg，HArg，（Me.sub.2）Arg，（Et.sub.2）Arg，Abu，Ala，Gly，His，Lys或其α-R'取代衍生物，Dtc，Tpr和Pro中选择的D-或L-氨基酸；B为Arg，HArg，NArg，（Me.sub.2）Arg，（Et.sub.2）Arg和Lys或其α-R'取代衍生物中选择的D-或L-氨基酸；Q不存在或为Tyr，（Alk）Tyr，Phe，（4'W）Phe，HPhe，Phg，Pro，Trp，His，Ser，（Alk）Ser，Thr，（Alk）Thr，（Alk）Cys，（Alk）Pen，Ala，Val，Nva，Met，Leu，Ile，Nle和Nal或其α-R'取代衍生物中选择的D或L氨基酸；M不存在或为Gly或在n为1时为B-Gly-Glu-Q中选择的D-或L-氨基酸；W为卤素或Alk；R'为Alk或PhCH.sub.2；##STR2## 其中Z.sub.1和Z.sub.2通过L.sup.1和L.sup.2之间的共价键连接；或Z.sub.1和Z.sub.2一起构成氨基末端残基与羧基末端残基之间的共价键；L.sup.1和L.sup.2为--S--或--(CH.sub.2).sub.p--；X为R.sub.4R.sub.5N或H；Y为H，CONR.sub.1R.sub.2或CO.sub.2R.sub.2；R.sub.1和R.sub.2为H，Alk或（CH.sub.2).sub.pAr；R.sub.3和R.sub.3'为H，Alk，（CH.sub.2).sub.pAr或一起为--(CH.sub.2).sub.4--或--(CH.sub.2).sub.5--；R.sub.4为H或Alk；R.sub.5为R.sub.11，R.sub.11CO，R.sub.11OCO，R.sub.11OCH(R.sub.11')CO，R.sub.11NHCH(R.sub.11')CO，R.sub.11SCH(R.sub.11')CO，R.sub.11SO.sub.2或R.sub.11SO；R.sub.6为Alk，OAlk，卤素或X；R.sub.7为H，Alk，OAlk，卤素或Y；R.sub.8和R.sub.8'为H，Alk，（CH.sub.2).sub.pPh，（CH.sub.2).sub.pNph或一起为--(CH.sub.2).sub.4--或--(CH.sub.2).sub.5--；R.sub.9为H，Alk或Y；R.sub.10为H或Alk；R.sub.11和R.sub.11'为H，C.sub.1-5烷基，C.sub.3-7环烷基，Ar，Ar--C.sub.1-5烷基，Ar--C.sub.3-7环烷基；Ar为苯基或被一个或两个C.sub.1-5烷基，三氟甲基，羟基，C.sub.1-5烷氧基或卤素基取代的苯基；n为1或2；q为0或1；p为0，1，2或3；或其药学上可接受的盐；用于抑制血小板聚集的有效化合物，用于实现该活性的药物组合物，用于在哺乳动物中抑制血小板聚集和凝块形成的方法，以及用于防止纤溶疗法后血管再闭塞的方法。
• Di-<i>tert</i>-butyl Peroxide-Mediated Radical C(sp²/sp³)–S Bond Cleavage and Group-Transfer Cyclization
  作者：Kai Luo、Wen-Chao Yang、Kai Wei、Yue Liu、Jun-Ke Wang、Lei Wu

  DOI：10.1021/acs.orglett.9b02837

  日期：2019.10.4

  cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources

  公开了一种级联自由基C（sp2 / sp3）-S键裂解和基团转移环化的新策略。由烷基引发，含有脂肪族，芳基和杂芳族基团的2-异氰基芳基硫醚可以被裂解并精确地重新安装，得到苯并噻唑衍生物。机理研究表明，级联反应采用分子间途径，并且内部自由基源（R自由基）比源自二叔丁基过氧化物的甲基自由基具有更高的优先级。
• 一种以硫脲为硫源合成多取代2-芳基苯并噻 唑的方法
  申请人：南京理工大学

  公开号：CN104892545B

  公开（公告）日：2017-02-01

  本发明公开了以硫脲为硫源合成多取代2‑芳基苯并噻唑的方法。所述方法利用硫脲和氯苄反应原位生成S‑苄基异硫脲盐与邻氟硝基苯发生芳香亲核取代反应，再经一步还原“一锅法”得到中间产物邻氨基苯基苄硫醚；最后，邻氨基苯基苄硫醚通过铁催化的交叉脱氢偶联反应得到目标产物。相比于传统的合成方法，本发明具有显著的优点：(1)反应步骤短，通过三步简单的反就可以用简单的化学原料合成目标产物；(2)反应条件温和，原子经济性高，反应试剂相对安全廉价；(3)反应产率高，底物耐受性好，避免了危险、高毒试剂的使用，具有放大生产的可能性。
• Ali; Bennett; Calvo, Journal of Medicinal Chemistry, 1994, vol. 37, # 6, p. 769 - 780
  作者：Ali、Bennett、Calvo、Elliott、Hwang、Ku、Lago、Nichols、Romoff、Shah、Vasko、Wong、Yellin、Yuan、Samanen

  DOI：——

  日期：——
• Synthesis of 2-Substituted 2,3-Dihydro-1,4-benzothiazine-3-thiones via Iminophosphoranes
  作者：Masahiko Takahashi、Masaru Ohba

  DOI：10.3987/com-95-7171

  日期：——

  2-(Substituted methylsulfanyl)anilines (5) were treated with triphenylphosphine dibromide to yield iminophosphoranes (6), whose aza-Wittig reaction with carbon disulfide gave 2-(substituted methylsulfanyl)phenyl isothiocyanates(8). Cyclization of 8 by strong bases afforded 2-substituted 2,3-dihydro-1,4-benzothiazine-3-thiones (10).