E-2,2-dimethyl-5-(1-methyl-4-phenylbutadienyl)-3(2H)-furanone | 74796-42-2

• 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: E-2,2-dimethyl-5-(1-methyl-4-phenylbutadienyl)-3(2H)-furanone
• 英文别名: 2,2-dimethyl-5-[(2E,4E)-5-phenylpenta-2,4-dien-2-yl]furan-3-one
• CAS: 74796-42-2
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: NMJIFTNSMYYVMJ-ZHSLHGDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-羟基-3-甲基-2-丁酮 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 正丁基锂 、 三乙胺 、 二异丙胺 、 N,N'-二环己基碳二亚胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.5h， 生成 E-2,2-dimethyl-5-(1-methyl-4-phenylbutadienyl)-3(2H)-furanone
  参考文献：
  名称：

  Synthesis and configurational assignment of geiparvarin: a novel antitumor agent

  摘要：

  DOI：

  10.1021/jo00316a018

文献信息

• Synthesis of geiparvarin: a novel antitumor agent possessing a 3(2H)-furanone ring
  作者：Amos B. Smith、Paula J. Jerris

  DOI：10.1016/s0040-4039(00)71453-5

  日期：1980.1

  The first synthesis of geiparvarin as well as assignment of configuration of the previously undefined trisubstituted olefinic bond has been achieved.

  已经实现了GEP1的首次合成以及先前未定义的三取代烯烃键的构型分配。
• An Entry to 5-(1-Alkenyl)-3(2<i>H</i>)-furanones through Cycloaddition of Phosphorus-Functionalized Nitrile Oxide to Acetylene Alcohols. An Effective Synthesis of Geiparvarin
  作者：Otohiko Tsuge、Shuji Kanemasa、Hiroyuki Suga

  DOI：10.1246/cl.1987.323

  日期：1987.2.5

  α-(diethoxyphosphoryl)acetonitrile oxide to acetylene alcohols is followed by an alkylation, a reductive cleavage of the N–O bond, and an acid-catalyzed cyclization to form 5-(diethoxyphosphorylmethyl)-3(2H)-furanones in good yields. Subsequent Horner-Emmons olefination using triethylamine and lithium bromide furnishes E-isomers of 5-(1-alkenyl)-3(2H)-furanones as major products. This method has been applied

  α-（二乙氧基磷酰基）乙腈氧化物环加成到乙炔醇，然后进行烷基化、N-O 键的还原断裂和酸催化环化反应，形成 5-（二乙氧基磷酰基甲基）-3（2H）-呋喃酮产量。随后使用三乙胺和溴化锂的 Horner-Emmons 烯化提供 5-(1-烯基)-3(2H)-呋喃酮的 E-异构体作为主要产物。该方法已应用于 Geiparvarin 的短合成。
• Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates
  作者：Daniele Simoni、Stefano Manfredini、Mojgan Aghazadeh Tabrizi、Rita Bazzanini、Pier G. Baraldi、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00115a004

  日期：1991.11

  In an attempt to determine some of the structural features of geiparvarin (1) that account for its cytostatic activity in vitro, a series of geiparvarin analogues (10a-i, 1, 12, and 14-16) which contain novel modifications in the region of the olefinic double bond and of the coumarin moiety have been designed and synthesized. Among the derivatives containing a carbamate moiety, only the analogues containing a carbamate group linked to an alkyl moiety 10b-i were endowed with potent cytostatic activity, whereas the corresponding benzene derivative 10a was devoid of any antiproliferative activity. 6-Methoxygeiparvarin 101 proved equally effective as geiparvin (1), while compounds containing an additional double bond at the side chain (12 and 14-16) were invariably 5-100-fold less effective than geiparvarin. Diene derivative 15, bearing a coumarin moiety, was essentially inactive against murine (L1210, FM3A) tumor cells but exhibited good activity against human (Molt/4F, MT-4) tumor cells.
• SAKAI, TAKASHI;KOHDA, KAZUHIKO;TSUBOI, SADAO;UTAKA, MASANORI;TAKEDA, AKIR+, BULL. CHEM. SOC. JAP., 60,(1987) N 8, 2911-2915
  作者：SAKAI, TAKASHI、KOHDA, KAZUHIKO、TSUBOI, SADAO、UTAKA, MASANORI、TAKEDA, AKIR+

  DOI：——

  日期：——
• Synthesis and configurational assignment of geiparvarin: a novel antitumor agent
  作者：Paula J. Jerris、Amos B. Smith

  DOI：10.1021/jo00316a018

  日期：1981.1