1-(4-Chlorophenyl)-4-ethoxy-1,2,5,6-tetrahydropyridine | 263008-90-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-Chlorophenyl)-4-ethoxy-1,2,5,6-tetrahydropyridine
• 英文别名: 1-(4-chlorophenyl)-4-ethoxy-3,6-dihydro-2H-pyridine
• CAS: 263008-90-8
• 化学式: C₁₃H₁₆ClNO
• 分子量: 237.729
• InChiKey: QYFSGHZFAQSPKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  377.1±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-Chlorophenyl)-4-ethoxy-1,2,5,6-tetrahydropyridine 在 四乙基氟化铵水合物 、 甲胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.75h， 生成 2'-O-[1-(4-Chlorophenyl)-4-ethoxypiperidin-4-yl]guanosine
  参考文献：
  名称：

  Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides

  摘要：

  讨论了在寡核苷酸合成中，十个1-芳基-4-甲氧基哌啶-4-基（R = Me，包括先前报道的Ctmp 5和Fpmp 6）保护基对2'-羟基功能的酸催化去除的相对速率。这些研究导致开发了1-(4-氯苯基)-4-乙氧基哌啶-4-基（Cpep）保护基8（R = Et，R1 = R2 = H，R3 = Cl），其在pH 0.5下比Ctmp和Fpmp群更加稳定，而在pH 3.75下更加不稳定。研究了核苷酸基在低pH和高pH下对2'-O-Fpmp和2'-O-Ctmp保护基稳定性的影响。

  DOI：

  10.1039/a908149f
• 作为产物：
  描述：

  1-(4-氯苯基)-哌啶-4-酮 在 三氟化硼乙醚 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-(4-Chlorophenyl)-4-ethoxy-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides

  摘要：

  讨论了在寡核苷酸合成中，十个1-芳基-4-甲氧基哌啶-4-基（R = Me，包括先前报道的Ctmp 5和Fpmp 6）保护基对2'-羟基功能的酸催化去除的相对速率。这些研究导致开发了1-(4-氯苯基)-4-乙氧基哌啶-4-基（Cpep）保护基8（R = Et，R1 = R2 = H，R3 = Cl），其在pH 0.5下比Ctmp和Fpmp群更加稳定，而在pH 3.75下更加不稳定。研究了核苷酸基在低pH和高pH下对2'-O-Fpmp和2'-O-Ctmp保护基稳定性的影响。

  DOI：

  10.1039/a908149f

文献信息

• Synthesis of unsaturated phosphatidylinositol 4,5-bisphosphate and analogues
  作者：Nitesh Panchal、Piers R. J. Gaffney

  DOI：10.1039/b907551h

  日期：——

  fatty acid esters, as well as phosphorothioate and acetylenic analogues. This strategy depends on masking the phosphate charges with base-labile cyanoethyl esters, and the hydroxyls of the target with mild acid-labile protecting groups. A two-step basic then acidic global unblocking of orthogonal protecting groups provides the target lipid. A xanthenylidene acetal was used for key temporary protection

  描述了一种合成磷脂酰肌醇 4,5-二磷酸 [PtdIns(4,5)P 2 ]的新方法，与不饱和脂肪酸酯以及硫代磷酸酯和炔类似物。该策略取决于屏蔽磷酸盐带有碱不稳定的氰乙基酯，目标的羟基带有温和的酸不稳定保护基团。正交保护基团的两步碱性然后酸性全局解锁提供了目标脂质。一种亚蒽乙缩醛用于 4,5-二醇的关键临时保护，6- O用 1-(4-氯苯基)-4-乙氧基哌啶-4-基保护 (心电图) 缩醛。
• Synthesis of 3’,5’-cyclic diguanylic acid (cdiGMP) Using 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl as a Protecting Group for 2’-hydroxy Functions of Ribonucleosides
  作者：Hongbin Yan、Aimé López Aguilar

  DOI：10.1080/15257770601112762

  日期：2007.3

  convenient synthesis of 3',5'-cyclic diguanylic acid via the modified H-phosphonate approach. The 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) group was used as protecting group for the 2'-hydroxy functions of ribonucleosides. Complete unblocking of the fully protected 3',5'-cyclic diguanylic acid gave cdiGMP as a homogeneous compound in an excellent yield.

  我们在此报告了通过修饰的H-膦酸酯方法方便地合成3'，5'-环二鸟苷酸。将1-（4-氯苯基）-4-乙氧基哌啶-4-基（Cpep）基团用作核糖核苷的2'-羟基官能团的保护基。完全保护的3'，5'-环二鸟苷酸完全解封，以极好的收率得到cdiGMP，为均相化合物。
• LARGE-SCALE SYNTHESIS OF “Cpep” RNA MONOMERS AND THEIR APPLICATION IN AUTOMATED RNA SYNTHESIS
  作者：R. T. Pon、S. Yu、T. Prabhavalkar、T. Mishra、B. Kulkarni、Y. S. Sanghvi

  DOI：10.1081/ncn-200060150

  日期：2005.4.1

  Small interfering RNAs (siRNA) are the latest candidates for oligonucleotide-based therapeutics. Should siRNA be successful in clinical trials, a huge demand for synthetic RNA is anticipated. We believe that 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl(Cpep) is an ideal 2'-protecting group for large-scale syntheses. Unlike 2'-silyl groups, mild acid hydrolysis instead of fluoride ion is used for the 2'-deprotection. The syntheses of 2'-Cpep protected nucleosides (A, Q G, and U) has been accomplished on a 0.5 Kg scale. The 2'-Cpep monomers were transformed into 3'-O-phosphoramidites for conventional automated solid-phase synthesis. Cost-effective processes for large-scale synthesis of Cpep monomers and initial automated solid-phase synthesis are demonstrated.
• Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides
  作者：Wayne Lloyd、Colin B. Reese、Quanlai Song、Anthony M. Vandersteen、Cristina Visintin、Pei-Zhou Zhang

  DOI：10.1039/a908149f

  日期：——

  The comparative rates of acid-catalysed removal of ten 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined.

  讨论了在寡核苷酸合成中，十个1-芳基-4-甲氧基哌啶-4-基（R = Me，包括先前报道的Ctmp 5和Fpmp 6）保护基对2'-羟基功能的酸催化去除的相对速率。这些研究导致开发了1-(4-氯苯基)-4-乙氧基哌啶-4-基（Cpep）保护基8（R = Et，R1 = R2 = H，R3 = Cl），其在pH 0.5下比Ctmp和Fpmp群更加稳定，而在pH 3.75下更加不稳定。研究了核苷酸基在低pH和高pH下对2'-O-Fpmp和2'-O-Ctmp保护基稳定性的影响。