ethyl 2-cyano-2-(2,2-dimethyl-tetrahydropyran-4-ylidene)acetate | 64792-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: ethyl 2-cyano-2-(2,2-dimethyl-tetrahydropyran-4-ylidene)acetate
• 英文别名: Ethyl 2-cyano-2-(2,2-dimethyloxan-4-ylidene)acetate
• CAS: 64792-49-0
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: VULAFJKFYCZNGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-2-(2,2-dimethyl-tetrahydropyran-4-ylidene)acetate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以62.7%的产率得到Ethyl (2,2-dimethyl-4-tetrahydropyranyl)cyanoacetate
  参考文献：
  名称：

  Synthesis and mutagenic action of tetrahydropyranyl-and tetrahydrothiopyranyl pyrazoles and pyrimidines

  摘要：

  DOI：

  10.1007/bf00768246
• 作为产物：
  描述：

  四氢-2 2-二甲基-4H-吡喃-4-酮 、 氰乙酸乙酯 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 以80 %的产率得到ethyl 2-cyano-2-(2,2-dimethyl-tetrahydropyran-4-ylidene)acetate
  参考文献：
  名称：

  COMPOUNDS FOR INCREASING THE NICOTINAMIDE ADENINE DINUCLEOTIDE IN A SUBJECT AND METHODS OF USE THEREOF

  摘要：

  根据本公开的目的，如本文所体现和广泛描述的，本公开在一个方面涉及可增加烟酰胺腺嘌呤二核苷酸（NAD + ）的化合物。通过提高受试者体内烟酰胺腺嘌呤二核苷酸的含量，可以治疗或预防与烟酰胺腺嘌呤二核苷酸水平降低有关的疾病。在一个方面，提高 NAD + 可以减轻或改善帕金森病、阿尔茨海默病、亨廷顿病、多发性硬化症、淀粉样变性侧索硬化症、艾滋病诱发的痴呆症或癫痫的一种或多种症状。

  公开号：

  US20230365521A1

文献信息

• Synthesis and some reactions of 2-[4-(2-chlorobenzyl)-6,6-dimethyltetrahydropyran-4-yl]ethylamine
  作者：N. S. Arutyunyan、O. A. Papoyan、L. A. Akopyan、G. A. Gevorgyan、G. A. Panosyan

  DOI：10.1134/s1070363213100289

  日期：2013.10

  l)]acetate II. The decarbethoxylation of the latter results in 3-(2-chlorobenzyl)-6,6-dimethyltetrahydropyran-3yl]acetonitrile III, the reduction of which with lithium aluminum hydride gives rise to 2-[4-(2-chlorobenzylDOI: 10.1134/S1070363213100289

  先前合成的氰基(2,2-二甲基四氢吡喃-4-亚基)乙酸乙酯I [3]与2氯苄基氯化镁反应形成氰基[2,2-二甲基四氢吡喃-4-基-4-(2-氯苯基)]乙酸乙酯II。后者的脱羧基化生成 3-(2-氯苄基)-6,6-二甲基四氢吡喃-3 基]乙腈 III，用氢化铝锂还原生成 2-[4-(2-氯苄基 DOI: 10.1134/S1070363213100289)
• 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