4-(3,6-dihydro-2H-thiopyran-4-yl)morpholine | 55436-25-4

• 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-(3,6-dihydro-2H-thiopyran-4-yl)morpholine
• 英文别名: 1-Morpholino-<4-thia-cyclohexen-(1)>；3,6-Dihydro-4-morpholino-2H-thiopyran；4-Morpholino-1-thia-cyclohexen-(3)；4-Thiacyclohexanon-morpholinenamin；4-morpholino-5,6-dihydro-2H-thiopyran
• CAS: 55436-25-4
• 化学式: C₉H₁₅NOS
• 分子量: 185.29
• InChiKey: WINCLTDZBUTMHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,6-dihydro-2H-thiopyran-4-yl)morpholine 在 甲醇 、 9-borabicyclo[3.3.1]nonane dimer 作用下， 生成 3,6-二氢-2H-噻喃
  参考文献：
  名称：

  Hydroboration. 86. Convenient conversion of aldehydes and ketones into the corresponding alkenes via hydroboration of their enamines. A remarkably simple synthesis of either (Z)- or (E)-alkenes

  摘要：

  Aldehydes and ketones are converted into the corresponding alkenes via hydroboration of their enamines. Hydroboration of aldehyde enamines by 9-borabicyclo[3.3.1]nonane (9-BBN), followed by methanolysis, affords the corresponding terminal alkenes in 75-90% yields. Unsaturated aldehyde enamines produce the corresponding dienes under these conditions. Enamines derived from substituted cyclic ketones and heterocyclic ketones are readily accommodated in this reaction to afford the corresponding alkenes in very good yields. The synthesis of pure (Z)- or (E)-alkenes is readily achieved from the same acyclic ketone enamine by modification of the hydroboration-elimination procedure: (A) hydroboration by 9-BBN followed by methanolysis or (B) hydroboration by borane methyl sulfide (BMS) followed by methanolysis and hydrogen peroxide oxidation. Mechanistic rationale is provided.

  DOI：

  10.1021/jo00004a038
• 作为产物：
  描述：

  吗啉 、 2,3-dihydro-4H-thiopyran-4-one 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 4-(3,6-dihydro-2H-thiopyran-4-yl)morpholine
  参考文献：
  名称：

  [EN] NOVEL TRICYCLIC DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  [FR] NOUVEAUX DÉRIVÉS TRICYCLIQUES OU LEURS SELS PHARMACEUTIQUEMENT ACCEPTABLES, PROCÉDÉ DE PRÉPARATION DE CES DERNIERS ET COMPOSITION PHARMACEUTIQUE LES CONTENANT

  摘要：

  公开号：

  WO2009061131A3

文献信息

• v-Triazolines. Part 7. 3-Arylaminothiophens from hexahydrothiopyrano[3,4-d]-v-triazoles
  作者：Donato Pocar、Luisa Maria Rossi、Riccardo Stradi、Pasqualina Trimarco

  DOI：10.1039/p19770002337

  日期：——

  tetrahydrothiopyran-4-one with secondary amines and aryl azides. 1-aryl-7a-amino-1,3a,4,6,7,7a-hexahydrothiopyrano[3,4-d]-v-triazoles (2) were obtained. On heating with acids, compounds (2) afforded mixtures of the corresponding 3-arylamino-2-methylthiophen (3) and 1-aryl-1,4,6,7-tetrahydrothiopyrano[3,4-d]-v-triazole (4). The triazoles (4) were also obtained on heating compounds (2) with sodium hydroxide in methanol

  通过用仲胺和芳基叠氮化物处理四氢噻喃-4-酮。1-芳基7A氨基1,3A，4,6,7,7a-hexahydrothiopyrano [3,4 d - ] v得到-triazoles（2）。上与酸，（2）化合物，得到相应的3-芳基氨基-2-甲基噻（3）和1-芳基-1,4,6,7- tetrahydrothiopyrano [3,4的混合物加热d ] - v -三唑（ 4）。通过在甲醇中用氢氧化钠加热化合物（2），也获得了三唑（4）。3,6-Dihydro-4-morpholino-2 H -thiopyran（6）用4-硝基苯基磺酰基叠氮化物处理，得到4-morpholino-3-（4-nitrophenylsulphonylamino）-3,6-dihydro-2 H -thiopyran（7） 。讨论了反应机理。
• Synthesis of diastereo- and enantiomerically pure α-amino-γ-oxo acid esters by reaction of acyliminoacetates with enamines derived from 6-membered ketones
  作者：Reiner Kober、Kyriakos Papadopoulos、Wolfgang Miltz、Dieter Enders、Wolfgang Steglich、Hans Reuter、Heinrich Puff

  DOI：10.1016/s0040-4020(01)96483-x

  日期：1985.1

  A new efficient diastereo- and enantioselective synthesis of α-amino-γ-oxo acid esters by reaction of acyliminoacetates with enamines is described. By employing the concept of double stereodifferentiation, complete asymmetric induction (de ≧99.9%) for the C-C bond formation is obtained. Desulphurization of a sulphur containing product leads to the corresponding acyclic amino acid derivatives. The

  描述了一种新的有效的非对映体和对映体选择性合成的方法，该方法通过酰氨基乙酸酯与烯胺的反应来合成α-氨基-γ-氧代酸酯。通过采用双重立体分化的概念，获得了用于CC键形成的完全不对称诱导（de≥99.9％）。含硫产物的脱硫产生相应的无环氨基酸衍生物。几乎完整的反非对映选择性和对映选择性是由Diels-Alder过渡态解释的。
• Synthesis and evaluation of tricyclic derivatives containing a non-aromatic amide as inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1)
  作者：Chun-Ho Park、Kwangwoo Chun、Bo-Young Joe、Ji-Seon Park、Young-Chul Kim、Ji-Soo Choi、Dong-Kyu Ryu、Seong-Ho Koh、Goang Won Cho、Seung Hyun Kim、Myung-Hwa Kim

  DOI：10.1016/j.bmcl.2010.02.014

  日期：2010.4

  Highly potent poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors, including 9-hydroxy-1,2-dihydro-4H-thiopyrano[3,4-c]quinolin-5(6H)-one derivatives with a non-aromatic A-ring, were synthesized. Among the derivatives, 12a showed low nanomolar enzyme and cellular activity (IC50 = 42 nM, ED50 = 220 nM) with good water solubility. Further, 12a exhibited microsomal stability in vitro and brain permeability

  高效聚（ADP-核糖）聚合酶-1（PARP-1）抑制剂，包括9-羟基-1,2-二氢-4 H-硫代吡喃并[3,4- c ]喹啉-5（6 H）-一衍生物具有非芳族A环的化合物被合成。在这些衍生物中，12a显示出低纳摩尔酶和细胞活性（IC 50  = 42 nM，ED 50  = 220 nM），并具有良好的水溶性。此外，12a表现出体外微粒体稳定性和体内脑通透性。
• Reactions of<i>N</i>-Acyl-<i>N</i>-(2,2,2-trichloroethylidene)amines with Enamines
  作者：Wolfgang Miltz、Wolfgang Steglich

  DOI：10.1055/s-1990-27002

  日期：——

  The reaction of N-acyl-N-(2,2,2-trichloroethylidene)amines with cyclic enamines affords chiral 2,2,2-trichloroethyl amine derivatives with high diastereo- and enantioselectivity.

  N-酰基-N-(2,2,2-三氯亚乙基)胺与环烯胺反应生成手性 2,2,2-三氯乙胺衍生物，具有很高的非对映和对映选择性。
• Synthesis and evaluation of thiopyrano[3,4-c]quinoline-9-carboxamide derivatives as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1)
  作者：Chun-Ho Park、Kwangwoo Chun、Bo-Young Joe、Jong-Hee Choi、Han-Chang Lee、Il-Whea Ku、Hyun Young Kim、Seong-Ho Koh、Goang Won Cho、Seung Hyun Kim、Myung-Hwa Kim

  DOI：10.1007/s00044-011-9673-6

  日期：2012.8

  A series of poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors, 5-oxo-2,4,5,6-tetrahydro-1H-thiopyrano[3,4-c]quinoline-9-carboxamide derivatives, were successfully synthesized and their PARP-1 inhibitory activity was evaluated. These compounds were prepared from carboxylic acid 7 and the appropriate amines, and a number of the synthesized compounds were found to have significant PARP-1 activity. Among

  一系列聚（ADP-核糖）聚合酶-1（PARP-1）抑制剂，5-氧代-2,4,5,6-四氢-1 H-硫代吡喃并[3,4- c ]喹啉-9-羧酰胺衍生物，成功合成，并评估其对PARP-1的抑制活性。这些化合物是由羧酸7和适当的胺制备的，发现许多合成的化合物都具有明显的PARP-1活性。其中，9m在PARP-1酶促测定和基于细胞的测定中显示出有效的活性（IC 50  = 0.045μM，ED 50  = 0.54μM）。分子模型研究证实了所获得的生物学结果。