翅茎西番莲果提取物 | 36394-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 翅茎西番莲果提取物
• 英文名称: 4-hydroxy-5-phenyl-4-cyclopentene-1,3-dione
• 英文别名: 4-hydroxy-5-phenyl-4-cyclopenten-1,3-dione；4-Hydroxy-5-phenylcyclopent-4-ene-1,3-dione
• CAS: 36394-22-6
• 化学式: C₁₁H₈O₃
• mdl: MFCD00013411
• 分子量: 188.183
• InChiKey: FDFWUEDHNVOGMV-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  翅茎西番莲果提取物 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-Hydroxy-5-phenyl-4-cyclopenten-1,2,3-trion
  参考文献：
  名称：

  Yamazaki,T. et al., Chemical and pharmaceutical bulletin, 1972, vol. 20, # 2, p. 238 - 245

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Ethoxy-5-phenyl-cyclopent-4-en-1,3-dion 在 盐酸 、 sodium phosphate 作用下， 反应 11.5h， 生成 翅茎西番莲果提取物
  参考文献：
  名称：

  抗凝剂芳烷基和芳基亚烷基环戊-4-烯-1,3-二酮

  摘要：

  使用六种标题化合物中的两种，对大鼠单次口服给药后 (165-330 毫克/千克) 凝血酶原水平可以达到低于标准的 15%。合适的氧代烷基环戊烯二酮可以环化为 1H -茚 - 1,5 (6H) - 二酮 6a 或 7,7a - 二氢 - 1H - 茚酮 6b。两者都是强抗凝剂。

  DOI：

  10.1002/ardp.19843170910

文献信息

• The Reaction Studies of α-Chloroformylarylhydrazines with Thiols, Thioureas and α-Cyclodiketones
  作者：Wen-Fa Kuo、Ming-Shyue Wu、Chun-Yen Chiu、Mou-Yung Yeh

  DOI：10.1002/jccs.200100036

  日期：2001.4

  types of reactions. Further studies on the reaction of α-chloroformylarylhydrazines 1 with thiourea compounds confirmed a novel cyclization and de-cyclization mechanism, which led to give 2-arylhydrazinecarboximidamides 5 and 1,3,4-thiadiazolin-5-ones 6. In addition, various 1,3,4-oxadiazines 9 were obtained by reacting α-chloroformylarylhydrazines with α-cyclodiketones, showing ring cyclization was involved

  α-氯甲酰芳基肼 1 与各种类型的硫醇、硫脲和 α-环二酮的反应已被深入研究。当 α-氯甲酰基芳基肼与硫醇反应时，通过硫酯化获得 1-芳基肼硫代碳酸酯 2。另一方面，化合物3是α-氯甲酰芳基肼与含硫杂环化合物反应得到的，这表明这些反应的机理完全不同。对 α-氯甲酰芳基肼 1 与硫脲化合物反应的进一步研究证实了一种新的环化和脱环机制，从而得到 2-芳基肼甲脒 5 和 1,3,4-噻二唑啉-5-酮 6。此外，各种 1 ,3,4-恶二嗪 9 由 α-氯甲酰芳基肼与 α-环二酮反应得到，
• Intermolecular N-H...O Hydrogen Bonding Assisted by Resonance. II. Self Assembly of Hydrogen-Bonded Secondary Enaminones in Supramolecular Catemers
  作者：V. Bertolasi、P. Gilli、V. Ferretti、G. Gilli

  DOI：10.1107/s0108768197008677

  日期：1998.2.1

  The crystal structures of 15 compounds containing the 2-en-3-amino-1-one heterodienic system and forming intermolecular N—H...O hydrogen bonds assisted by resonance (RAHB) are reported: (1) 3-phenylamino-2-cyclohexen-1-one; (2) 3-(4-methoxyphenylamino)-2-cyclohexen-1-one; (3) 3-(4-chlorophenylamino)-2-cyclohexen-1-one; (4) 3-(4-methoxyphenylamino)-2-methyl-2-cyclohexen-1-one; (5) 3-(4-methoxyphenylamino)-5-methyl-2-cyclohexen-1-one; (6) 3-isopropylamino-5,5-dimethyl-2-cyclohexen-1-one; (7) 3-phenylamino-5,5-dimethyl-2-cyclohexen-1-one; (8) 3-(3-methoxyphenylamino)-5,5-dimethyl-2-cyclohexen-1-one; (9) N,N-3-aza-pentane-1,5-bis[1-(3-oxo-5,5-dimethyl-1-cyclohexenyl)]; (10) 3-phenylamino-6,6-dimethyl-2-cyclohexen-1-one; (11) 3-(2-methoxyphenylamino)-6,6-dimethyl-2-cyclohexen-1-one; (12) 3-(3-chlorophenylamino)-6,6-dimethyl-2-cyclohexen-1-one; (13) 3-(4-chlorophenylamino)-6,6-dimethyl-2-cyclohexen-1-one; (14) 1-(4-chlorophenyl)-4-(4-chlorophenylamino)-6-methyl-2-pyridone; (15) 3-(4-chlorophenylamino)-5-phenyl-2-cyclopenten-1,4-dione. All compounds form intermolecular N—H...O=C hydrogen bonds assisted by resonance connecting the heteroconjugated enaminonic groups in infinite chains. Chain morphologies are analyzed to find out crystal engineering rules able to predict and interpret the crystal packing. Simple secondary enaminones [i.e. (1)–(13) together with a number of structures retrieved from the Cambridge Structural Database] are found to form hydrogen bonds having π-delocalizations, as characterized by a C=O bond-length average of 1.239 ± 0.004 Å, and hydrogen-bond strengths, represented by the N...O average distance of 2.86 ± 0.05 Å, very similar to those previously found for amides. Enaminones, however, can be easily substituted by chemical groups able to influence both π-conjugations and N...O hydrogen-bond distances. Some substituted enaminones, retrieved from the literature, display, in fact, N...O hydrogen-bond distances as short as 2.627 Å and large π-delocalizations with C=O double-bond distances as long as 1.285 Å. These effects appear to be associated with (a) the presence of further π-conjugated systems involving the C=O and NH groups of the enaminone moiety or (b) the transformation of the enaminone carbonyl group in an amidic function.

  报告了 15 种含有 2-en-3-amino-1-one 杂二烯体系并通过共振（RAHB）形成分子间 N-H...O 氢键的化合物的晶体结构：(1) 3-苯基氨基-2-环己烯-1-酮；(2) 3-(4-甲氧基苯基氨基)-2-环己烯-1-酮；(3) 3-(4-氯苯基氨基)-2-环己烯-1-酮；(4) 3-(4-甲氧基苯基氨基)-2-甲基-2-环己烯-1-酮；(5) 3-(4-甲氧基苯基氨基)-5-甲基-2-环己烯-1-酮； (6) 3-异丙基氨基-5,5-二甲基-2-环己烯-1-酮； (7) 3-苯基氨基-5,5-二甲基-2-环己烯-1-酮； (8) 3-(3-甲氧基苯基氨基)-5,5-二甲基-2-环己烯-1-酮；(9) N,N-3-氮杂戊烷-1,5-双[1-(3-氧代-5,5-二甲基-1-环己烯基)]； (10) 3-苯基氨基-6,6-二甲基-2-环己烯-1-酮； (11) 3-(2-甲氧基苯基氨基)-6,6-二甲基-2-环己烯-1-酮； (12) 3-(3-氯苯基氨基)-6,6-二甲基-2-环己烯-1-酮；(13) 3-(4-氯苯基氨基)-6,6-二甲基-2-环己烯-1-酮； (14) 1-(4-氯苯基)-4-(4-氯苯基氨基)-6-甲基-2-吡啶酮； (15) 3-(4-氯苯基氨基)-5-苯基-2-环戊烯-1,4-二酮。所有化合物都在共振的辅助下形成分子间 N-H...O=C 氢键，并将异共轭的烯酰胺基团连接成无限的链。通过对链形态的分析，可以找出预测和解释晶体堆积的晶体工程学规则。研究发现，简单的仲烯酮（即 (1)-(13) 以及从剑桥结构数据库中检索到的一些结构）形成的氢键具有 π 位移，其特点是 C=O 键平均长度为 1.239 ± 0.004 Å，氢键强度以 N...O 平均距离 2.86 ± 0.05 Å 表示，与之前发现的酰胺非常相似。然而，烯酰胺酮很容易被化学基团取代，从而影响π-共轭和 N...O 氢键距离。事实上，从文献中检索到的一些取代的烯酰胺酮显示出短至 2.627 Å 的 N...O 氢键距离和长达 1.285 Å 的 C=O 双键距离的大π异位。这些效应似乎与 (a) 涉及烯酮分子的 C=O 和 NH 基团的进一步 π 共轭体系的存在或 (b) 烯酮羰基在脒基功能中的转化有关。
• Ruthenium Complexes of Electronically Coupled Cyclopentadienone Ligands – Catalysts for Transformations of Propargyl Alcohols
  作者：Edgar Haak

  DOI：10.1002/ejoc.200700064

  日期：2007.6

  A series of donor- and acceptor-substituted ruthenium cyclopentadienone complexes were synthesized and their catalytic activities towards propargyl alcohols focused on amination reactions have been investigated. It is shown that the substituents of the cyclopentadienone ligand determine the mode of activation of propargyl alcohols by these complexes leading to different central intermediates in catalytic

  合成了一系列供体和受体取代的钌环戊二烯酮配合物，并研究了它们对专注于胺化反应的炔丙醇的催化活性。结果表明，环戊二烯酮配体的取代基决定了这些配合物对炔丙醇的活化模式，导致催化循环中的不同中心中间体。可以实现炔丙醇向α-或β-氨基酮、烯氨基酮、α,β-不饱和亚胺、酮、烯烃和共轭烯炔的催化转化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Alpha-(1,3-dicarbonylenol ether) methyl ketones as cysteine protease inhibitors
  申请人：——

  公开号：US20020128434A1

  公开（公告）日：2002-09-12

  Cysteine protease inhibitors which deactivate the protease by covalently bonding to the cysteine protease and releasing the enolate of a 1,3-dicarbonyl (or its enolic form). The cysteine protease inhibitors of the present invention accordingly comprise a first portion which targets a desired cysteine protease and positions the inhibitor near the thiolate anion portion of the active site of the protease, and a second portion which covalently bonds to the cysteine protease and irreversibly deactivates that protease by providing a carbonyl or carbonyl-equivalent which is attacked by the thiolate anion of the active site of the cysteine protease to sequentially cleave a &bgr;-dicarbonyl enol ether leaving group.

  半胱氨酸蛋白酶抑制剂通过共价键结合半胱氨酸蛋白酶并释放1,3-二羰基（或其烯醇形式）的烯醇酸使蛋白酶失活。因此，本发明的半胱氨酸蛋白酶抑制剂包括第一部分，该部分针对所需的半胱氨酸蛋白酶并将抑制剂定位于蛋白酶活性位点的巯基阴离子部分附近，以及第二部分，该部分与半胱氨酸蛋白酶共价键结合，并通过提供被半胱氨酸蛋白酶活性位点上的巯基阴离子攻击的羰基或羰基等效物，不可逆地使该蛋白酶失活，以顺序裂解β-二羰基烯醇醚离基。
• Substituted cyclopentane-di- and triones, their preparation and their use as chloride channel blockers
  申请人：BAYER AG

  公开号：EP0701988A1

  公开（公告）日：1996-03-20

  The invention relates to the use of substituted cyclopentane-diones and cyclopentane-triones for the preparation of medicaments which are suitable for controlling airway diseases, secretory diarrhoe and inflammatory diseases.

  本发明涉及使用取代的环戊烷二酮和环戊烷三酮制备适用于控制气道疾病、分泌性腹泻和炎症性疾病的药物。