N,N'-bis(2-phenylethyl)hexane-1,6-diamine | 850481-05-9

• 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: N,N'-bis(2-phenylethyl)hexane-1,6-diamine
• 英文别名: N,N'-diphenethyl-hexanediyldiamine；N,N'-Diphenaethyl-hexandiyldiamin；dopexamine；Dopexamine Dihydrochloride Impurity J [Ep Impurity]
• CAS: 850481-05-9
• 化学式: C₂₂H₃₂N₂
• 分子量: 324.509
• InChiKey: RSIPJAZEPYGJBO-UHFFFAOYSA-N

物化性质

• 沸点：
  464.2±33.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-溴丙基)苯二胺 、 N,N'-bis(2-phenylethyl)hexane-1,6-diamine 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以55%的产率得到2-[3-[[6-[[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl](2-phenylethyl)amino]hexyl](2-phenylethyl)amino]propyl]isoindole-1,3-dione
  参考文献：
  名称：

  Allosteric Modulators of the Tertiary Alkanebisamino-Type. Variation of the Substitution of the Middle Chain Nitrogens

  摘要：

  Synthesis pathways of high flexibility for variously substituted alkanebisamine-type allosteric modulators of musearinic receptors capable of passing the blood-brain barrier were developed starting either from N,N'-(hexane-1,6-diyl)bistosylamide or adipic acid chloride. Pharmacological evaluation of some representative compounds revealed the allosteric potency to fall in a submicromolar range.

  DOI：

  10.1007/s00706-004-0218-2
• 作为产物：
  描述：

  N,N'-diphenethyl-adipamide 在 diborane(6) 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到N,N'-bis(2-phenylethyl)hexane-1,6-diamine
  参考文献：
  名称：

  Allosteric Modulators of the Tertiary Alkanebisamino-Type. Variation of the Substitution of the Middle Chain Nitrogens

  摘要：

  Synthesis pathways of high flexibility for variously substituted alkanebisamine-type allosteric modulators of musearinic receptors capable of passing the blood-brain barrier were developed starting either from N,N'-(hexane-1,6-diyl)bistosylamide or adipic acid chloride. Pharmacological evaluation of some representative compounds revealed the allosteric potency to fall in a submicromolar range.

  DOI：

  10.1007/s00706-004-0218-2

文献信息

• Amine derivatives, processes for their production and pharmaceutical compositions containing them
  申请人：FISONS plc

  公开号：EP0072061A1

  公开（公告）日：1983-02-16

  There are described compounds of formula I, in which D, represents a group of formula II, where R, and R5, or H3 and R5 may form a chain -CH2CH2-, or R4 and R5 may form a chain -CH2-, or R3, R4 and R5 are each hydrogen, the remainder of R,, R3 and R4, which may be the same or different, being hydrogen, alkyl or phenyl, none, one or two of R6, R7, R8 and R, represent hydroxy and the remainder represent hydrogen, X represents a chain -(CH2)n-, optionally substituted by hydroxy, n is an integer from 1 to 7 inclusive, D2 represents hydrogen, alkyl, phenyl; alkyl substituted by one or more of hydroxy, pyridyl, phenyl; or alkyl substituted by phenyl which in turn is substituted by halogen, alkyl, amino, alkoxy or nitro, or D2 represents a group of formula III, where R2 and R12, or R,o and R12 may form a chain -CH2-CH2-, or R11 and R12 may form a chain -CH2-, or R10, R,, and R12 are each hydrogen, the remainder of R2, R10 and R11, which may be the same or different being hydrogen, alkyl or phenyl, none, one or two of R13, R14, R15 and R16 represent hydroxy, and the remainder represent hydrogen, or R2 and D2, together with the nitrogen atom to which they are attached, form a 5 or 6 membered heterocyclic ring, provided that when X is not substituted by hydroxy and i) when R3, R4 and R5 are hydrogen, R, and R2 are both hydrogen or lower alkyl, and two of R6, R7, R8 and R9 are hydroxy, D2 is not identical to D1, or ii) when R,, R3, R4, R5, R6, R7, R8 and R9 are hydrogen, R2 and D2 do not each represent lower alkyl, or do not together with the nitrogen atom to which they are attached, form a 5 or 6 membered heterocyclic ring, or iii) when R,, R4, R5, R6, R7, R8 and R9 are hydrogen, and R3 is alkyl, D2 is not identical to D1, or iv) when R, is phenyl, R3 and R5 together form the chain -CH2CH2-, R6, R7, R8 and R9 are hydrogen, n is 1, D2 and R2 do not each represent hydrogen or alkyl, or do not together form a heterocyclic ring, and pharmaceutically acceptable derivatives thereof. There are also described methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.

  所述化合物为式 I、 其中 D 代表式 II 的基团、 其中 R 和 R5，或 H3 和 R5 可形成链 -CH2CH2-，或 R4 和 R5 可形成链 -CH2CH2-，或 R3、R4 和 R5 各为氢，R、R3 和 R4 的其余部分（可相同或不同）为氢、烷基或苯基、 R6、R7、R8 和 R 的一个或两个不代表羟基，其余代表氢、 X 代表链-(CH2)n-，可选择被羟基取代、 n 是 1 到 7（包括 7）的整数、 D2 代表氢、烷基、苯基；被羟基、吡啶基、苯基中的一个或多个取代的烷基；或被苯基取代的烷基，而苯基又被卤素、烷基、氨基、烷氧基或硝基取代、 或 D2 代表式 III 的基团、 其中 R2 和 R12，或 R,o 和 R12 可形成链 -CH2-CH2-，或 R11 和 R12 可形成链 -CH2-，或 R10、R,, 和 R12 各为氢、 R2、R10 和 R11 的其余部分（可以相同或不同）为氢、烷基或苯基、 R13、R14、R15 和 R16 中没有一个或两个代表羟基，其余代表氢、 或 R2 和 D2 与它们所连接的氮原子一起形成一个 5 或 6 个成员的杂环、 但当 X 未被羟基取代且 i) 当 R3、R4 和 R5 为氢，R 和 R2 均为氢或低级烷基，且 R6、R7、R8 和 R9 中的两个为羟基时，D2 与 D1 不相同，或 ii) 当 R、R3、R4、R5、R6、R7、R8 和 R9 为氢，R2 和 D2 不各自代表低级烷基，或不与所连接的氮原子一起形成 5 或 6 位杂环时，或 iii) 当 R、R4、R5、R6、R7、R8 和 R9 为氢，且 R3 为烷基时，D2 与 D1 不完全相同，或 iv) 当 R 为苯基时，D2 与 D1 不完全相同。 当 R、R4、R5、R6、R7、R8 和 R9 为氢，且 R3 为烷基时，D2 与 D1 不相同，或 iv) 当 R、R4、R5、R6、R7、R8 和 R9 为氢，且 R3 为烷基时，D2 与 D1 不相同，或 及其药学上可接受的衍生物。 此外，还描述了制造这些化合物的方法和含有这些化合物的药物组合物，如心脏病组合物。
• Goodson et al., British Journal of Pharmacology and Chemotherapy, 1948, vol. 3, p. 61
  作者：Goodson et al.

  DOI：——

  日期：——
• Wegler; Pieper, Chemische Berichte, 1950, vol. 83, p. 6,10
  作者：Wegler、Pieper

  DOI：——

  日期：——
• Allosteric Modulators of the Tertiary Alkanebisamino-Type. Variation of the Substitution of the Middle Chain Nitrogens
  作者：Rainer Pick、Seraina Duda-Johner、Christian Tr�nkle、Klaus Mohr、Ulrike Holzgrabe

  DOI：10.1007/s00706-004-0218-2

  日期：2004.12

  Synthesis pathways of high flexibility for variously substituted alkanebisamine-type allosteric modulators of musearinic receptors capable of passing the blood-brain barrier were developed starting either from N,N'-(hexane-1,6-diyl)bistosylamide or adipic acid chloride. Pharmacological evaluation of some representative compounds revealed the allosteric potency to fall in a submicromolar range.