4,4-Diethoxy-2-phenylbutylamine | 106658-99-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4-Diethoxy-2-phenylbutylamine
• 英文别名: 4,4-Diethoxy-2-phenylbutan-1-amine
• CAS: 106658-99-5
• 化学式: C₁₄H₂₃NO₂
• 分子量: 237.342
• InChiKey: PMPYYPQZLISYOS-UHFFFAOYSA-N

物化性质

• 沸点：
  110-115 °C(Press: 0.1 Torr)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-Diethoxy-2-phenylbutylamine 在 吡啶 、 盐酸 、 sodium hydroxide 、 戊醇 、 盐酸羟胺 、 sodium 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2α,5α,7α,8aβ)-4-amino-5-chloro-2-methoxy-N-(octahydro-5-methyl-2-phenylindolizin-7-yl)benzamide
  参考文献：
  名称：

  Substituted benzamides with conformationally restricted side chains. 2. Indolizidine derivatives as central dopamine receptor antagonists

  摘要：

  The substituted benzamides metoclopramide (1) and clebopride (3) are stimulants of gastric motility. They are also central dopamine receptor antagonists with 3 being the more potent. This is presumed to be due to an additional interaction of its N-benzyl group with the receptor. The effect of restricting the conformation of this group by replacing the N-benzylpiperidine side chain of 3 by phenyl-substituted quinolizidines and indolizidines has been investigated. Only the indolizidines had significant activity, the nature of which depended upon the orientation of the phenyl substituent. The 2 alpha-phenyl isomers 5d-h were potent central dopamine D2 receptor antagonists with 5h showing selectivity for the limbic system. The 2 beta-phenyl isomer 5c was a gastric motility stimulant devoid of significant central dopamine receptor antagonist activity. Implications on receptor models are discussed.

  DOI：

  10.1021/jm00117a008
• 作为产物：
  描述：

  α-(2,2-diethoxyethyl)benzyl cyanide 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以85%的产率得到4,4-Diethoxy-2-phenylbutylamine
  参考文献：
  名称：

  King, Frank D., Journal of the Chemical Society. Perkin transactions I, 1986, p. 447 - 454

  摘要：

  DOI：

文献信息

• Development and application of allyl, 2-sulfonylethyl and 2-thioethyl carbamate linkers for solid phase N-acyliminium ion chemistry
  作者：Jan H. van Maarseveen、Wim J. N. Meester、Johan J. N. Veerman、Chris G. Kruse、Pedro H. H. Hermkens、Floris P. J. T. Rutjes、Henk Hiemstra

  DOI：10.1039/b100998m

  日期：——

  work up procedure which is required for the removal of the remains of the cleavage cocktail. The SEC linker is excellently stable to both Lewis and protic acidic conditions combined with a moderate base stability thus allowing the use of amines as reactants or bases in subsequent reactions. Cleavage of SEC linker bound amines was easily effected by treatment of the resins with a cocktail of 1 M NaOMe

  我们已经评估了烯丙基，2-磺酰基乙基（SEC）和2-硫乙基（TEC）氨基甲酸酯连接体系统在固相支持的N-酰基亚胺离子化学中的应用。作为模型反应，进行了均烯丙基胺（通过固定化伯氨基甲酸酯开始的三组分方案）和2-取代吡咯烷（通过氨基甲酸酯键合的4,4-二乙氧基-2-苯基丁胺）的合成。所需的前体p用廉价的起始原料高产率地制备了碳酸-硝基苯酯树脂。在所需的阳离子反应条件下，所有连接基均证明是稳定的。氨基甲酸烯丙酯连接体的一个严重缺点是繁琐的后处理步骤，这对于除去裂解混合物的残余物是必需的。SEC接头在路易斯和质子酸性条件下均具有出色的稳定性，并具有适度的碱稳定性，因此可在后续反应中使用胺作为反应物或碱。通过用1 M NaOMe的THF-MeOH（2 ∶1）混合物对树脂进行处理，可以很容易地实现SEC连接基结合胺的裂解。TEC连接器发现了最广泛的合成范围，该连接器结合了对N所需的阳离子条件具有足够的
• Azabicyclobenzamides, their preparation and their pharmaceutical compositions
  申请人：BEECHAM GROUP PLC

  公开号：EP0094744A1

  公开（公告）日：1983-11-23

  A compound of formula (I), or a pharmaceutically acceptable salt, N-oxide or solvent adduct thereof: wherein: R1 is C1-6 alkoxy, C1-6 alkylthio or, together with R6 is C1-2 alkylene, and one of R2, R3 and R4 is hydrogen and the other two together are C1-2 alkylenedioxy, or the other two are the same or different and are selected from the class of hydrogen. halogen, trifluoromethyl. C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio. C1-7 acyl, C, 7 acylamino. C1-6 alkylsulphonyl, C1-6 alkylsulphinyl hydroxy, nitro or amino, aminocarbonyl or aminosulphonyl optionally N-substituted by one or two C1-6 alkyl, C3-8 cycloalkyl, phenyl or phen C1-4 alkyl groups or optionally N-disubstituted by C4-5 polymethylene, or R, and R2 together are C1-2 alkylenedioxy, and R3 and R4 together are C1-2 alkylenedioxy or R3 and R4 are the same or different and are selected from the previously defined class of substituents; R5 is hydrogen or as defined with R1; R6 is hydrogen or C1-6 alkyl; and Ar is phenyl or thien-2-yl or thien-3-yl, optionally substituted by one or two groups, which are the same or different selected from C1-4 alkoxy, trifluoromethyl, halogen, carboxy, esterified carboxy or C1-4 alkyl optionally substituted by hydroxy, C1-4alkoxy, carboxy, esterified carboxy or in vivo hydrolysable C1-4 acyloxy. Ar being in the 3β configuration as defined in formula (VIII) ; and Ar may also have the a-configuration when one of R2, R3 and R4 is hydrogen and the other two are independently selected from optionally substituted amino or aminosulphonyl as defined, C1-6 alkylsulphonyl or C1-6 alkylsulphinyl; or R1 and R2 together are C1-2 alkylenedioxy and R3 and R4 are independently selected from the same group of substituents, compositions thereof and processes therefor.

  式 (I) 的化合物或其药学上可接受的盐、N-氧化物或溶剂加合物： 其中 R1为 C1-6烷氧基、C1-6烷硫基或与 R6 一起为 C1-2 亚烷基，R2、R3 和 R4 中的一个为氢，另外两个一起为 C1-2 亚烷基二氧基，或另外两个相同或不同且选自氢、卤素、三氟甲基、C1-6 烷基、C1-6 烷氧基、C1-6 烷硫基、C1-6 亚烷基二氧基、C1-6 烷硫基、C1-6 亚烷基二氧基、C1-6 烷硫基C1-6烷基，C1-6烷氧基，C1-6烷硫基。C1-7酰基、C, 7酰氨基。C1-6烷基磺酰基、C1-6烷基亚磺酰基 羟基、硝基或氨基、氨基羰基或氨基磺酰基，可任选被一个或两个 C1-6 烷基、C3-8 环烷基、苯基或苯 C1-4 烷基 N-取代，或任选被 C4-5 聚亚甲基 N-取代，或 R 和 R2 同为 C1-2 烷二氧基，R3 和 R4 同为 C1-2 烷二氧基，或 R3 和 R4 相同或不同，且选自前面定义的取代基类别； R5 是氢或与 R1 所定义的相同； R6 是氢或 C1-6 烷基；以及 Ar 是苯基或噻吩-2-基或噻吩-3-基，任选被一个或两个相同或不同的基团取代，这些基团选自 C1-4 烷氧基、三氟甲基、卤素、羧基、酯化羧基或任选被羟基、C1-4 烷氧基、羧基、酯化羧基或体内可水解的 C1-4 丙烯酸氧基取代的 C1-4 烷基。 当 R2、R3 和 R4 中的一个为氢，另外两个独立地选自任选取代的氨基或胺磺酰基（如定义）、C1-6 烷基磺酰基或 C1-6 烷基亚磺酰基时，Ar 为式（VIII）中定义的 3β 构型；Ar 也可具有 a 构型；或 R1 和 R2 共同为 C1-2 烷二氧基，R3 和 R4 独立选自同一组取代基、其组合物及其工艺。
• King, Frank D., Journal of the Chemical Society. Perkin transactions I, 1986, p. 447 - 454
  作者：King, Frank D.

  DOI：——

  日期：——
• A novel acid stable/base labile carbamate linker for N-acyliminium ion reactions on solid support
  作者：Johan J.N. Veerman、Floris P.J.T. Rutjes、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1016/s0040-4039(99)01263-0

  日期：1999.8

  The development of a novel carbamate linker optimized for solid phase N-acyliminium ion chemistry is reported. Some 2- and 2,4-substituted pyrrolidines were synthesized via addition of several carbon nucleophiles to immobilized N-acyliminium ions. A beta-sulfonylethyl carbamate linker appeared especially useful; readily synthesized, stable towards Lewis acids and easily cleavable. (C) 1999 Elsevier Science Ltd. All rights reserved.
• KING, F. D., J. CHEM. SOC. PERKIN TRANS., 1986, N 3, 447-453
  作者：KING, F. D.

  DOI：——

  日期：——