2-丙烯醛,3-[4-[(四氢-2H-吡喃-2-基)氧代]苯基]-,(E)- | 103909-81-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 2-丙烯醛,3-[4-[(四氢-2H-吡喃-2-基)氧代]苯基]-,(E)-
• 英文名称: (E)-3-(4-(tetrahydro-2H-pyran-2yloxy)phenyl)acryl aldehyde
• 英文别名: (E)-3-(4-(tetrahydropyran-2-yloxy)phenyl)acrylaldehyde；(E)-3-[4-(oxan-2-yloxy)phenyl]prop-2-enal
• CAS: 103909-81-5
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: AIRFQYFWQKBNGV-ONEGZZNKSA-N

物化性质

• 熔点：
  96-98 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  412.7±40.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丙烯醛,3-[4-[(四氢-2H-吡喃-2-基)氧代]苯基]-,(E)- 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
  参考文献：
  名称：

  Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids

  摘要：

  A general method for the synthesis of substituted (1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9-20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure-activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.105
• 作为产物：
  描述：

  对羟基苯甲醛 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 0.83h， 生成 2-丙烯醛,3-[4-[(四氢-2H-吡喃-2-基)氧代]苯基]-,(E)-
  参考文献：
  名称：

  Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids

  摘要：

  A general method for the synthesis of substituted (1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9-20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure-activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.105

文献信息

• Synthesis of Two Alnustone-Like Natural Diarylheptanoids via 4 + 3 Strategy
  作者：Serdar Burmaoğlu、Hülya Çelik、Süleyman Göksu、Ahmet Maraş、Ramazan Altundaş、Hasan Seçen

  DOI：10.1080/00397910802542036

  日期：2009.4.7

  Abstract The first total synthesis of (4E,6E)-1,7-bis(3,4-dihydroxyphenyl)-hepta-4,6-dien-3-one and an alternative synthesis of (4E,6E)-1,7-bis(4-hydroxyphenyl)-hepta-4,6-dien-3-one, two natural diarylheptanoids, mainly based on Claisen–Schmidt condensation were described. The crucial steps of the syntheses were the condensation of OH-protected 4-aryl-2-butanones with OH-protected 3-aryl-acrylaldehydes

  摘要 (4E,6E)-1,7-bis(3,4-dihydroxyphenyl)-hepta-4,6-dien-3-one 的首次全合成和 (4E,6E)-1,7 的替代合成-bis(4-hydroxyphenyl)-hepta-4,6-dien-3-one, 两种天然二芳基庚烷类化合物，主要基于 Claisen-Schmidt 缩合。合成的关键步骤是 OH 保护的 4-芳基-2-丁酮与 OH 保护的 3-芳基-丙烯醛通过原位烯化反应缩合，然后脱去 OH 基团，得到相应的天然二芳基庚烷。
• Novel dihydropyridine derivatives and process for preparing the same
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0145434A2

  公开（公告）日：1985-06-19

  Dihydropyridine derivatives and salts thereof represented by the general formula, which possess excellent calcium antagonist effect, hypoten- sive effect, platelets aggregation inhibitory effect, phosphodiesterase inhibitory effect, calmodulin inhibitory effect and peroxidized lipid lowering effect, and thus dihydropyridine derivatives and salts thereof are useful as a coronary blood flow improving agent such as coronary vasodilator, hypotensive agent, prophylaxis and treating agents for thrombosis, phosphodiesterase inhibitory agent, peroxidized lipid metabolism lowering agent, anti-inflammatory agent and others.

  通式代表的二氢吡啶衍生物及其盐、 具有良好的钙拮抗剂作用、降血压作用、血小板聚集抑制作用、磷酸二酯酶抑制作用、钙调素抑制作用和过氧化脂质降低作用、因此，二氢吡啶衍生物及其盐类可用作冠状动脉血流改善剂，如冠状动脉血管扩张剂、降血压剂、血栓预防和治疗剂、磷酸二酯酶抑制剂、过氧化脂质代谢降低剂、消炎剂等。
• Process for preparing novel dihydropyridine derivatives
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0173126A1

  公开（公告）日：1986-03-05

  Process for preparing novel dihydropyridine deriva-- tives and salts thereof represented by the general formula (1). [wherein R', R2 and R4 are each a lower alkyl group; R3 is a nitro group or a lower alkyl group which may have 1 to 3 halogen atoms as the substituents; R5 is a phenyl group which may have 1 to 3 substituents selected from the group consisting of a lower alkoxy group, a halogen atom, a lower alkylthio group, a hydroxyl group, a lower alkonyloxy group, a tetrahydropyranyloxy group, a lower alkoxy-lower alkoxy group; and A is an unsaturated straight- or branched-chain hydrocarbon residue]. The novel dihydropyridine derivatives and salts thereof are useful as coronary blood flow improving agents such as coronary vasodilator, hypotensive agent, prophylaxis and treating agents for thrombosis, phosphodiesterase inhibitory agents, peroxidized lipid metabolism lowering agents, antiinflammatory agents as well as anti-tumorigenic agents.

  由通式（1）表示的新型二氢吡啶衍生物及其盐的制备方法。 [其中 R'、R2 和 R4 各为低级烷基；R3 为硝基或低级烷基，其取代基可为 1 至 3 个卤素原子；R5 是苯基，可具有 1 至 3 个取代基，这些取代基选自低级烷氧基、卤素原子、低级烷硫基、羟基、低级烷酰氧基、四氢吡喃氧基、低级烷氧基-低级烷氧基组成的组；以及 A 是不饱和直链或支链烃残基]。新型二氢吡啶衍生物及其盐类可用作冠状动脉血流改善剂，如冠状动脉血管扩张剂、降血压剂、血栓预防和治疗剂、磷酸二酯酶抑制剂、过氧化脂质代谢降低剂、抗炎剂以及抗肿瘤剂。
• US4795814A
  申请人：——

  公开号：US4795814A

  公开（公告）日：1989-01-03
• US5034395A
  申请人：——

  公开号：US5034395A

  公开（公告）日：1991-07-23