2-(4-fluorophenyl)methyl-1,3-dithiane | 140377-42-0

• 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: 2-(4-fluorophenyl)methyl-1,3-dithiane
• 英文别名: 2-[(4-fluorophenyl)methyl]-1,3-dithiane
• CAS: 140377-42-0
• 化学式: C₁₁H₁₃FS₂
• 分子量: 228.355
• InChiKey: YEQKOMNALWGRAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴苯甲醚 、 2-(4-fluorophenyl)methyl-1,3-dithiane 在 potassium tert-butylate 、 palladium diacetate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 反应 24.0h， 以90%的产率得到(E)-(4-fluorostyryl)(3-((4-methoxyphenyl)thio)propyl)sulfane
  参考文献：
  名称：

  Synthesis of Disubstituted Dithioethers: tert-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C–S Bond Formation

  摘要：

  We report the tandem base-promoted elimination/ring-opening of 2-benzyl-1,3-dithianes with subsequent cross coupling of the pendent thiol with a range of aryl bromides. A simple Pd(OAc)(2)/Xantphos catalyst system affects this new reaction and is compatible with a wide range of functional groups, including heteroaromatic coupling partners. The transformation proceeds in good to excellent yields (6999%) and exhibits strong stereoselectivity, forming the E-alkene as the major diastereomer. This new methodology provides access to nonsymmetric propylene styryl/aryl dithioethers, a previously undisclosed motif.

  DOI：

  10.1021/acs.joc.5b00547
• 作为产物：
  描述：

  1,3-二噻烷 、 4-氟溴苄 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.33h， 以73%的产率得到2-(4-fluorophenyl)methyl-1,3-dithiane
  参考文献：
  名称：

  Synthesis of Disubstituted Dithioethers: tert-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C–S Bond Formation

  摘要：

  We report the tandem base-promoted elimination/ring-opening of 2-benzyl-1,3-dithianes with subsequent cross coupling of the pendent thiol with a range of aryl bromides. A simple Pd(OAc)(2)/Xantphos catalyst system affects this new reaction and is compatible with a wide range of functional groups, including heteroaromatic coupling partners. The transformation proceeds in good to excellent yields (6999%) and exhibits strong stereoselectivity, forming the E-alkene as the major diastereomer. This new methodology provides access to nonsymmetric propylene styryl/aryl dithioethers, a previously undisclosed motif.

  DOI：

  10.1021/acs.joc.5b00547

文献信息

• Biogenic amine uptake inhibitors
  申请人：Abbott Laboratories

  公开号：US05180733A1

  公开（公告）日：1993-01-19

  Compounds of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein M is 0, 1 or 2 and n is 0 or 1; R.sup.1 is hydrogen or lower alkyl; R.sup.2 is C.sub.1 -C.sub.6 -alkyl substituted with a heterocyclic group or C.sub.7 -C.sub.16 -arylalkyl, wherein the aryl group is unsubstituted or substituted with from one to three non-hydrogen members independently selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxy, amino and C.sub.1 -C.sub.6 -alkylamino; R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkyl, halogen, and halo-C.sub.1 -C.sub.6 -alkyl, or any two of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 taken together form a methylenedioxy group; and R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl. These compounds are useful as inhibitors of the neuronal uptake of biogenic amines and for the treatment of affective disorders, such as, for example, depression.

  该化合物的公式为：##STR1## 或其药学上可接受的盐，其中M为0、1或2，n为0或1；R.sup.1为氢或较低的烷基；R.sup.2为带有杂环基团的C.sub.1-C.sub.6烷基或C.sub.7-C.sub.16芳基烷基，其中芳基未取代或由一到三个非氢成员独立选择的卤素，C.sub.1-C.sub.6烷基，卤代C.sub.1-C.sub.6烷基，C.sub.1-C.sub.6烷氧基，羟基，氨基和C.sub.1-C.sub.6烷基氨基取代；R.sup.3、R.sup.4、R.sup.5和R.sup.6独立选择自氢，C.sub.1-C.sub.6烷氧基，C.sub.1-C.sub.6烷基，卤素和卤代C.sub.1-C.sub.6烷基的群，或R.sup.3、R.sup.4、R.sup.5和R.sup.6中的任意两个形成亚甲二氧基基团；R.sup.7为氢或C.sub.1-C.sub.6烷基。这些化合物可用作生物胺神经摄取抑制剂，并用于治疗情感障碍，例如抑郁症。
• Biogentic amine uptake inhibitors
  申请人：Abbott Laboratories

  公开号：US05248677A1

  公开（公告）日：1993-09-28

  Compounds of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein m is 0, 1 or 2 and n is 0 or 1; R.sup.1 is hydrogen or lower alkyl; R.sup.2 is C.sub.1 -C.sub.6 -alkyl substituted with a heterocyclic group or C.sub.7 -C.sub.16 -arylalkyl, wherein the aryl group is unsubstituted or substituted with from one to three non-hydrogen members independently selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxy, amino and C.sub.1 -C.sub.6 -alkylamino; R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkyl, halogen, and halo-C.sub.1 -C.sub.6 -alkyl, or any two of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 taken together form a methylenedioxy group; and R.sup.7 is hydrogen or C.sub.1 -C.sub.6 -alkyl. These compounds are useful as inhibitors of the neuronal uptake of biogenic amines and for the treatment of affective disorders, such as, for example, depression.

  化合物的公式为：##STR1## 或其药学上可接受的盐，其中m为0、1或2，n为0或1；R.sup.1为氢或较低的烷基；R.sup.2为含杂环基团的C.sub.1-C.sub.6烷基或C.sub.7-C.sub.16芳基烷基，其中芳基团未取代或取代有1至3个非氢成员，所述非氢成员独立地选自卤素、C.sub.1-C.sub.6烷基、卤代C.sub.1-C.sub.6烷基、C.sub.1-C.sub.6烷氧基、羟基、氨基和C.sub.1-C.sub.6烷基氨基的群；R.sup.3、R.sup.4、R.sup.5和R.sup.6独立地选自氢、C.sub.1-C.sub.6烷氧基、C.sub.1-C.sub.6烷基、卤素和卤代C.sub.1-C.sub.6烷基的群，或R.sup.3、R.sup.4、R.sup.5和R.sup.6中的任意两个结合形成亚甲二氧基基团；R.sup.7为氢或C.sub.1-C.sub.6烷基。这些化合物可用作生物胺神经元摄取抑制剂，并用于治疗情感障碍，例如抑郁症。
• US5180733A
  申请人：——

  公开号：US5180733A

  公开（公告）日：1993-01-19
• US5248677A
  申请人：——

  公开号：US5248677A

  公开（公告）日：1993-09-28
• Synthesis of Disubstituted Dithioethers: <i>tert</i>-Butoxide Promoted Elimination/Ring Opening of 1,3-Dithianes Followed by Palladium-Catalyzed C–S Bond Formation
  作者：Nissa Abidi、Jason R. Schmink

  DOI：10.1021/acs.joc.5b00547

  日期：2015.4.17

  We report the tandem base-promoted elimination/ring-opening of 2-benzyl-1,3-dithianes with subsequent cross coupling of the pendent thiol with a range of aryl bromides. A simple Pd(OAc)(2)/Xantphos catalyst system affects this new reaction and is compatible with a wide range of functional groups, including heteroaromatic coupling partners. The transformation proceeds in good to excellent yields (6999%) and exhibits strong stereoselectivity, forming the E-alkene as the major diastereomer. This new methodology provides access to nonsymmetric propylene styryl/aryl dithioethers, a previously undisclosed motif.