ethyl <2,2-dimethyl-4-(p-fluorophenyl)-4-tetrahydropyranyl>cyanacetate | 120729-52-4

• 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: ethyl <2,2-dimethyl-4-(p-fluorophenyl)-4-tetrahydropyranyl>cyanacetate
• 英文别名: ethyl 2-cyano-2-(4-(4-fluorophenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl)acetate；Ethyl cyano[4-(4-fluorophenyl)-2,2-dimethyltetrahydro-2H-pyran-4-yl]acetate；ethyl 2-cyano-2-[4-(4-fluorophenyl)-2,2-dimethyloxan-4-yl]acetate
• CAS: 120729-52-4
• 化学式: C₁₈H₂₂FNO₃
• 分子量: 319.376
• InChiKey: AKKZDKYRMLSGJP-UHFFFAOYSA-N

物化性质

• 沸点：
  196 °C(Press: 4 Torr)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl <2,2-dimethyl-4-(p-fluorophenyl)-4-tetrahydropyranyl>cyanacetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以64.2%的产率得到3-Amino-2-[4-(4-fluorophenyl)-2,2-dimethyloxan-4-yl]propan-1-ol
  参考文献：
  名称：

  Synthesis and study of the antiinflammatory properties of tetrahydropyran-substituted γ-aminopropanols

  摘要：

  DOI：

  10.1007/bf00764464
• 作为产物：
  描述：

  四氢-2 2-二甲基-4H-吡喃-4-酮 在 ammonium acetate 、 magnesium 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 27.0h， 生成 ethyl <2,2-dimethyl-4-(p-fluorophenyl)-4-tetrahydropyranyl>cyanacetate
  参考文献：
  名称：

  [EN] TETRAHYDROPYRAN-4-YLETHYLAMINO- OR TETRAHYDROPYRANYL-4-ETHYLOXY-PYRIMIDINES OR -PYRIDAZINES AS ISOPRENYLCYSTEINCARBOXYMETHYL TRANSFERASE INHIBITORS
  [FR] PYRIMIDINES OU PYRIDAZINES TÉTRAHYDROPYRAN-4-YLÉTHYLAMINO- OU TÉTRAHYDROPYRANYL-4-ÉTHYLOXY UTILES COMME INHIBITEURS DE L'ISOPRÉNYL-CYSTÉINE-CARBOXY-MÉTHYL-TRANSFÉRASE

  摘要：

  化合物的结构式（I）：其中：R1选自：（i）苯基，可选择一个氟原子取代；（ii）噻吩基；（iii）呋喃基；（iv）C1-4烷基；和（v）氢；R2选自：（II），R3选自：（III），X选自NH和O；R4选自苯基，5-成员杂环基或6-成员杂环基，均可选择一个或多个取代基，所述取代基选自：甲基，甲氧基，三氟甲基，三氟甲氧基，氰基，氟原子，-OC2H4OMe和吡唑基。

  公开号：

  WO2014041349A1

文献信息

• [EN] TETRAHYDROPYRAN-4-YLETHYLAMINO- OR TETRAHYDROPYRANYL-4-ETHYLOXY-PYRIMIDINES OR -PYRIDAZINES AS ISOPRENYLCYSTEINCARBOXYMETHYL TRANSFERASE INHIBITORS<br/>[FR] PYRIMIDINES OU PYRIDAZINES TÉTRAHYDROPYRAN-4-YLÉTHYLAMINO- OU TÉTRAHYDROPYRANYL-4-ÉTHYLOXY UTILES COMME INHIBITEURS DE L'ISOPRÉNYL-CYSTÉINE-CARBOXY-MÉTHYL-TRANSFÉRASE
  申请人：CANCER THERAPEUTICS CRC PTY LTD

  公开号：WO2014041349A1

  公开（公告）日：2014-03-20

  A compound of formula (I): wherein: R1 is selected from: (i) phenyl, optionally substituted by one fluoro group; (ii) thienyl; (iii) furanyl; (iv) C1-4 alkyl; and (v) H; R2 is selected from: (II), R3 is selected from: (III), X is selected from NH and O; R4 is selected from phenyl, a 5-membered heteroaryl or a 6-membered heteroaryl, all of which are optionally substituted by one or more substituents selected from the group consisting of: methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano, fluoro, -OC2H4OMe, and pyrazolyl.

  化合物的结构式（I）：其中：R1选自：（i）苯基，可选择一个氟原子取代；（ii）噻吩基；（iii）呋喃基；（iv）C1-4烷基；和（v）氢；R2选自：（II），R3选自：（III），X选自NH和O；R4选自苯基，5-成员杂环基或6-成员杂环基，均可选择一个或多个取代基，所述取代基选自：甲基，甲氧基，三氟甲基，三氟甲氧基，氰基，氟原子，-OC2H4OMe和吡唑基。
• ARUTYUNYAN, N. S.;AKOPYAN, L. A.;APOYAN, N. A.;TUMADZHYAN, A. E.;VARTANYA+, XIM.-FARMATS. ZH., 23,(1989) N, S. 182-184
  作者：ARUTYUNYAN, N. S.、AKOPYAN, L. A.、APOYAN, N. A.、TUMADZHYAN, A. E.、VARTANYA+

  DOI：——

  日期：——
• Discovery and SAR of Methylated Tetrahydropyranyl Derivatives as Inhibitors of Isoprenylcysteine Carboxyl Methyltransferase (ICMT)
  作者：Weston R. Judd、Paul M. Slattum、Khanh C. Hoang、Leena Bhoite、Liisa Valppu、Glen Alberts、Brita Brown、Bruce Roth、Kirill Ostanin、Liwen Huang、Daniel Wettstein、Burt Richards、J. Adam Willardsen

  DOI：10.1021/jm200249a

  日期：2011.7.28

  A series of tetrahydropyranyl (THP) derivatives has been developed as potent inhibitors of isoprenylcysteine carboxyl methyltransferase (ICMT) for use as anticancer agents. Structural modification of the submicromolar hit compound 3 led to the potent 3-methoxy substituted analogue 27. Further SAR development around the THP ring resulted in an additional 10-fold increase in potency, exemplified by analogue 75 with an IC50 of 1.3 nM. Active and potent compounds demonstrated a dose-dependent increase in Ras cytosolic protein. Potent ICMT inhibitors also reduced cell viability in several cancer cell lines with growth inhibition (GI(50)) values ranging from 0.3 to >100 mu M. However, none of the cellular effects observed using ICMT inhibitors were as pronounced as those resulting from a farnesyltransferase inhibitor.
• Synthesis and study of the antiinflammatory properties of tetrahydropyran-substituted γ-aminopropanols
  作者：N. S. Arutyunyan、L. A. Akopyan、N. A. Apoyan、A. E. Tumadzhyan、S. A. Vartanyan

  DOI：10.1007/bf00764464

  日期：1989.2