2-甲基-2-丙基(2E)-3-[4-(氰基甲基)苯基]丙烯酸酯 | 120225-74-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 2-甲基-2-丙基(2E)-3-[4-(氰基甲基)苯基]丙烯酸酯
• 英文名称: tert-butyl 4-(cyanomethyl)cinnamate
• 英文别名: tert-butyl (E)-3-[4-(cyanomethyl)phenyl]prop-2-enoate
• CAS: 120225-74-3
• 化学式: C₁₅H₁₇NO₂
• mdl: MFCD16293790
• 分子量: 243.305
• InChiKey: UHGFRQZECZHVKY-CMDGGOBGSA-N

物化性质

• 溶解度：
  二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基(2E)-3-[4-(氰基甲基)苯基]丙烯酸酯 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 异丙醇 为溶剂， 130.0 ℃ 、344.73 kPa 条件下， 反应 10.0h， 生成 2-<<4-<2-(tert-butoxycarbonyl)etyl>phenethyl>amino>-2',3'-O-isopropylideneadenosine-5'-N-ethylcarboxamide
  参考文献：
  名称：

  2-(Arylalkylamino)adenosin-5'-uronamides: a new class of highly selective adenosine A2 receptor ligands

  摘要：

  The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)-adenosin-5'-uronamides is described. Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor subtype on the basis of rat brain receptor binding. The general structure-activity relationship of this series of compounds is discussed both in terms of potency at A2 receptors as well as receptor subtype selectivity. It is possible to introduce a hydrophilic carboxyalkyl substituent to this series such as in CGS 21680A (3h) and still retain good potency and selectivity for A2 receptors. In addition, functional data in a perfused working rat heart model shows that these compounds possess full agonist properties at A2 receptors with 3h having a greater than 1500-fold separation between A2 (coronary vasodilatory) and A1 (negative chronotropic) receptor mediated events.

  DOI：

  10.1021/jm00169a015
• 作为产物：
  描述：

  丙烯酸叔丁酯 、 对溴苯乙腈 在 四丁基溴化铵 、 silica gel 、 potassium carbonate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以80%的产率得到2-甲基-2-丙基(2E)-3-[4-(氰基甲基)苯基]丙烯酸酯
  参考文献：
  名称：

  在层状双氢氧化物中引入钯（0）：一种用于球磨机中无溶剂和无配体Heck反应的可持续催化剂。

  摘要：

  在本文中，描述了通过共沉淀和还原方法合成负载在MgAl层状双氢氧化物（Pd / MgAl-LDHs）上的廉价，可重复使用且不含配体的Pd催化剂。将该催化剂用于室温下高速球磨（HSBM）条件下的Heck反应中。详细研究了磨球尺寸，磨球填充度，反应时间，转速和磨削助剂种类等对机械化学Heck反应收率的影响。XRD，ICP-MS和XPS的表征结果表明，Pd / MgAl-LDHs具有优良的织构特性，其层上具有零价Pd。反应结果表明该催化剂可用于HSBM系统中，以令人满意的产率提供多种Heck偶联产物。此外，

  DOI：

  10.3762/bjoc.13.160

文献信息

• 2-(N'-aralkylidenehydrazino)adenosines: potent and selective coronary vasodilators.
  作者：Kazunori Niiya、Robert D. Thompson、Scott K. Silvia、Ray A. Olsson

  DOI：10.1021/jm00102a008

  日期：1992.11

  Some of the analogues were quite active coronary vasodilators; 2-(N'-benzylidenehydrazino)adenosine, 2, and several of its para-substituted derivatives, namely, the fluoro (7), methyl (13), methoxy (16), and tert-butylcarbonylethyl, 31, had EC50s for coronary vasodilation in the range 1.7-3.2 nM. The selectivity ratios, EC50 (negative dromotropic)/EC50 (coronary vasodilatory), of these five analogues

  这项研究旨在开发2-（N'-亚烷基亚水合肼基）腺苷作为冠状动脉血管扩张剂。芳族醛或酮与2-肼基腺苷在回流的甲醇中的反应以高收率形成目标化合物2-27，为结晶产物。两种受体介导腺苷对心脏的作用。通过房室结的冲动传导迟缓是负性趋性作用，是腺苷对A1受体（A1AR）的作用的一个例子，冠状血管舒张反应反映了腺苷对A2受体（A2AR）的作用。因此，采用豚鼠心脏Langendorff制剂的生物测定法评估了2-27作为冠状动脉血管扩张剂的选择性。类似物2-27是弱的负性变色剂。最活跃的类似物2- [N' -（1-萘基甲基）肼基]-腺苷23的分子量为0.8 microM，比许多A1AR激动剂少几个数量级。一些类似物是相当活跃的冠状血管舒张剂。2-（N'-亚苄基肼基肼基）腺苷2及其几种对位取代衍生物，即氟（7），甲基（13），甲氧基（16）和叔丁基羰基乙基31对冠状动脉具有EC50。血管舒张范围为1.7-3
• N9-cyclopentyl-substituted adenine derivatives
  申请人：CIBA-GEIGY AG

  公开号：EP0267878A1

  公开（公告）日：1988-05-18

  The compounds of the formula I wherein R, R3 and R5 independently represent hydrogen or hydroxy provided that at least one of R, R3 and R5 represents hydroxy; R1 represents hydrogen, lower alkyl, C3-C7alkenyl, hydroxy-lower alkyl, C3-C6cycloalkyl, C3-C6cycloalkyl-lower alkyl, 2-norbornyl, 2-norbornyl-lower alkyl, aryl, aryl-lower alkyl, aryl-C3-C6cycloalkyl, 9-fluorenyl or 9-fluorenyl-lower alkyl; or R1 represents a bicyclic benzo-fused 5 or 6-membered saturated carbocyclic radical or a benzo fused 5 or 6-membered saturated heterocyclic radical containing a heteroatom selected from oxygen and sulfur directly attached to the fused benzene ring, any said bicyclic radicals being optionally substituted on the benzo portion by lower alkyl, lower alkoxy or halogen; R2 represents hydrogen, halogen, -SR1 or -N(R9)R1 in each of which R1 has meaning as defined hereinbefore provided that R1 in -SR1 does not represent hydrogen; R9 represents hydrogen or lower alkyl; R4 represents hydroxymethyl provided that R2 does not represent either hydrogen or -NHRI in which R1 represents either hydrogen or lower alkyl; or R4 represents lower alkoxymethyl, lower alkylthiomethyl or -CONHR6 in which R6 represents lower alkyl, aryl-lower alkyl, C3-Cscycloalkyl or hydroxy-lower alkyl; pharmaceutically acceptable ester derivatives thereof in which free hydroxy groups are esterified in form of a pharmaceutically acceptable ester; and salts thereof; methods for their preparation; and their use as adenosine receptor agonists are disclosed.

  式 I 的化合物 其中R、R3和R5独立地代表氢或羟基，但R、R3和R5中至少有一个代表羟基；R1代表氢、低级烷基、C3-C7烯基、羟基-低级烷基、C3-C6环烷基、C3-C6环烷基-低级烷基、2-降冰片基、2-降冰片基-低级烷基、芳基、芳基-低级烷基、芳基-C3-C6环烷基、9-芴基或9-芴基-低级烷基；或 R1 代表双环苯并 5 或 6 元饱和碳环基，或苯并 5 或 6 元饱和杂环基，其中含有一个选自氧和硫的杂原子，直接连接到苯并环上，任何上述双环基的苯并部分可选择被低级烷基、低级烷氧基或卤素取代；R2 代表氢、卤素、-SR1 或-N(R9)R1，其中每个 R1 的含义如前文所定义，条件是 -SR1 中的 R1 不代表氢；R9 代表氢或低级烷基；R4 代表羟甲基，条件是 R2 不代表氢或-NHRI，其中 R1 代表氢或低级烷基；或R4代表低级烷氧基甲基、低级烷硫基甲基或-CONHR6，其中R6代表低级烷基、芳基-低级烷基、C3-Cscycloalkyl或羟基-低级烷基；公开了其药学上可接受的酯衍生物，其中游离羟基以药学上可接受的酯的形式酯化；及其盐；其制备方法；及其作为腺苷受体激动剂的用途。
• Certain adenosine 5'-carboxamide derivatives
  申请人：CIBA-GEIGY AG

  公开号：EP0277917A2

  公开（公告）日：1988-08-10

  The compounds of the formula I wherein R represents hydrogen or lower alkyl; R¹ represents cyclo­alkyl, cycloalkyl-lower alkyl, 2-norbornanyl, 2-norbornanyl-lower alkyl, aryl, aryl-lower alkyl, aryl-cycloalkyl, 9-fluorenyl, diaryl-lower alkyl or 9-fluorenyl-lower alkyl; or R¹ represents a bicyclic benzo-fused 5- or 6-membered saturated carbocyclic radical or a benzo-fused 5- or 6-membered saturated heterocyclic radical containing a heteroatom selected from oxygen and sulfur which is directly attached to the fused benzene ring, any said bicyclic radical being unsubstituted or substituted on the benzo portion by lower alkyl, lower alkoxy, hydroxy, halogen or trifluoromethyl, or by a substituent -W-Z in which W represents a direct bond, lower alkylene, lower alkenylene, thio-lower alkylene or oxy-lowe alkylene and Z represents cyano, carboxy or carboxy derivatized in the form of a pharmaceutically acceptable ester or amide; R² represents hydrogen, lower alkyl or aryl-lower alkyl; R³ represents hydrogen or hydroxy; R⁴ represents hydrogen, lower alkyl, aryl-lower alkyl, cycloalkyl or hydroxy-lower alkyl; pharmaceutically accept­able ester derivatives thereof in which free hydroxy groups are esterified in form of a pharmaceutically acceptable ester; pharmaceutically acceptable salts thereof; their preparation, and their use as adenosine-2 receptor agonists are disclosed.

  式 I 的化合物 其中 R 代表氢或低级烷基；R¹ 代表环烷基、环烷基-低级烷基、2-降冰片烷基、2-降冰片烷基-低级烷基、芳基、芳基-低级烷基、芳基-环烷基、9-芴基、二芳基-低级烷基或 9-芴基-低级烷基；或 R¹ 代表双环苯并融合的 5 或 6 元饱和碳环基，或苯并融合的 5 或 6 元饱和杂环基，其中含有直接连接到融合苯环上的选自氧和硫的杂原子，任何上述双环基均未被取代或在苯并部分被低级烷基取代、低级烷氧基、羟基、卤素或三氟甲基，或取代基-W-Z，其中 W 代表直接键、低级亚烷基、低级亚烯基、硫代低级亚烷基或氧代低级亚烷基，Z 代表氰基、羧基或以药学上可接受的酯或酰胺形式衍生的羧基；R²代表氢、低级烷基或芳基-低级烷基；R³代表氢或羟基；R⁴代表氢、低级烷基、芳基-低级烷基、环烷基或羟基-低级烷基；公开了其药学上可接受的酯衍生物，其中游离羟基以药学上可接受的酯的形式酯化；其药学上可接受的盐；其制备及其作为腺苷-2 受体激动剂的用途。
• HUTCHISON, ALAN J.;WILLIAMS, MICHAEL;JESUS, REYNALDA DE;RINA, YOKOYAMA;OE+, J. MED. CHEM., 33,(1990) N, C. 1919-1924
  作者：HUTCHISON, ALAN J.、WILLIAMS, MICHAEL、JESUS, REYNALDA DE、RINA, YOKOYAMA、OE+

  DOI：——

  日期：——
• US4954504A
  申请人：——

  公开号：US4954504A

  公开（公告）日：1990-09-04