(E)-1,4-dimethoxy-2-styrylbenzene | 122950-69-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1,4-dimethoxy-2-styrylbenzene
• 英文别名: (E)-2,5-dimethoxystilbene；2,5-Dimethoxystilbene；1,4-dimethoxy-2-[(E)-2-phenylethenyl]benzene
• CAS: 122950-69-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: KUPZMZKMMSWRSG-CMDGGOBGSA-N

物化性质

• 熔点：
  46.2-47.5 °C(Solv: hexane (110-54-3))
• 沸点：
  374.5±11.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,4-dimethoxy-2-styrylbenzene 在 碘 作用下， 以 环己烷 为溶剂， 反应 10.0h， 以56%的产率得到1,4-二甲氧基-菲
  参考文献：
  名称：

  Photochemistry of stilbenes. 8. Eliminative photocyclization of o-methoxystilbenes

  摘要：

  DOI：

  10.1021/jo00280a032
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 在 喹啉 、 chromium(III) oxide 、 乙酸酐 、 三乙胺 、 copper(II) oxide 作用下， 反应 2.0h， 生成 (E)-1,4-dimethoxy-2-styrylbenzene
  参考文献：
  名称：

  Synthesis and biological evaluation of 1,1-Dichloro-2,3-diarylcyclopropanes as antitubulin and anti-breast cancer agents

  摘要：

  Z-1,1-Dichloro-2,3-diphenylcyclopropane (1) is an effective 'anti-breast cancer agent in rodents and in cell culture. We recently determined that 1 inhibits tubulin assembly in vitro. and causes microtubule loss in breast cancer cells, leading to accumulation in the G2/M portion of the cell cycle. Aryl ring-halogenated, methoxylated and benzyloxylated derivatives of 1, as well as its E-isomer and the dichlorocyclopropyl derivative of diethylstilbestrol (DES), were synthesized and tested for their ability to inhibit the assembly of tubulin into micro tubules. Including 1, 17 cyclopropyl compounds were tested. One (Z-1,1-dichloro-2-(4-methoxyphenyl)-3-phenylcyclopropane (12)) was found to be more active than 1. In addition, E-1,1-dichlorocyclopropylDES (17) was more potent than DES. The E-isomer of 1 (16) was inactive. The cytostatic activities of the compounds against MCF-7 and MDA-MB231 human breast cancer cells, and their abilities to perturb microtubules in MCF-7 cells were also evaluated. Z-Dichloro-2-(4-fluorophenyl)-3-phenylcyclo (5), Z-1,1-dichloro-2-(4-fluorophenyl)-3-(4-methoxyphenyl)cyclopropane (11), and Z-1,1-dichloro-2-(4-methoxyphenyl) -3-phenylcyclopropane (12) were more potent than 1 against the breast cancer cells. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00014-x

文献信息

• Synthesis and Nematocidal Activity of Hydroxystilbenes
  作者：Mohammad Ahad ALI、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.40.1130

  日期：1992.5.25

  Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed dy demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2, 6-dihydroxy-, 3, 4-dihydroxy-, 3, 5-dihydroxy-, 2, 2'-dihydroxy-, 3, 3'-dihydroxy-, 3, 4'-dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC)=30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.

  通过一种新的(Z)-(E)异构化方法随后进行脱甲基反应，从(E)/(Z)混合甲氧基二苯乙烯中合成了多种(E)-羟基二苯乙烯。当甲氧基二苯乙烯脱甲基生成羟基二苯乙烯时，表现出杀线虫活性。为了产生这种活性，C-2或C-3位置上必须有一个羟基。因此，2-羟基-、3-羟基-、2,6-二羟基-、3,4-二羟基-、3,5-二羟基-、2,2'-二羟基-、3,3'-二羟基-、3,4'-二羟基-、2-羟基-4-甲氧基-、5-羟基-2-甲氧基-、2-羟基-6-甲氧基-、6-烯丙氧基-2-羟基-、3-羟基-5-甲氧基-和5-烯丙氧基-3-羟基二苯乙烯表现出相当强的杀线虫活性。5-烯丙氧基-3-羟基二苯乙烯的活性最强[最小致死浓度（MLC）=30 μM]。(E)和(Z)异构体的活性相当。二氢衍生物，羟基联苄中也保留了这些活性，尽管较弱。
• Carbonyl–Olefin Cross‐Metathesis Through a Visible‐Light‐Induced 1,3‐Diol Formation and Fragmentation Sequence
  作者：Lena Pitzer、Frederik Sandfort、Felix Strieth‐Kalthoff、Frank Glorius

  DOI：10.1002/anie.201810221

  日期：2018.12.3

  cross‐metathesis is described. Photoinduced hole catalysis was used to promote the formation of 1,3‐diols from aldehydes and styrenes, which were then readily fragmented under acidic conditions to form the cross‐metathesis products. The use of 1,3‐diols as intermediates, rather than the energetically more demanding oxetanes, provides a new, orthogonal mechanistic strategy for carbonyl–olefin cross‐metathesis.

  描述了可见光介导的羰基烯烃交叉复分解方法。光诱导空穴催化用于促进醛和苯乙烯形成1,3-二醇，然后在酸性条件下容易裂解形成交叉复分解产物。使用1,3-二醇作为中间体，而不是对能量要求更高的氧杂环丁烷，为羰基烯烃交叉复分解提供了一种新的正交机理。此外，这种方法不需要任何金属，配体或添加剂，并为产品提供了高水平的E。 选择性。提供了一种机械原理，并得到了理论计算和实验的支持。此外，还介绍了一种新的基于a啶的光催化剂的实用合成方法，包括完整的表征。
• Substituted CIS- and trans-stilbenes as therapeutic agents
  申请人：Vander Jagt David L.

  公开号：US20070249647A1

  公开（公告）日：2007-10-25

  The present invention relates to method(s) of treating a subject afflicted with cancer or a precancerous condition, an inflammatory disease or condition, and/or stroke or other ischemic disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans-stilbene.

  本发明涉及治疗患有癌症或癌前病变、炎症性疾病或病情以及中风或其他缺血性疾病或病情的方法，该方法包括向需要的受试者或患者施用含有一定治疗有效量的取代的顺式或反式-芪的组合物。
• Synthesis, Structures and Topochemistry of 2-Monovinyl-Substituted 1,4-Benzoquinones
  作者：Hermann Irngartinger、Birgit Stadler

  DOI：10.1002/(sici)1099-0690(199804)1998:4<605::aid-ejoc605>3.0.co;2-2

  日期：1998.4

  resulting in the corresponding cyclobutanes 9. Topochemically controlled the dimers 9a−9c, 9e, 9l−9n, 9q, 9r and 9u with molecular Ci symmetry were formed whereas the dimers 9k and 9t have Cs symmetry. The structures of the cyclobutanes were determined by spectroscopical investigations and in the case of 9b, 9e and 9r additionally by X-ray analysis. Despite short contacts, crystals of 1f and 1i were photostable

  在取代醌的拓扑化学研究过程中，2-单乙烯基取代的 1,4-苯醌 1 是通过将相应的 1,4-二甲氧基苯衍生物 3 电化学氧化为醌二缩酮 4 并随后水解来合成的。在溶液中，芳基取代的乙烯基醌 1a-1t 经历了意想不到的 Diels-Alder 加成。通过光谱学和二聚体 8k 的 X 射线结构分析证明了反应的立体化学独特过程。作为拓扑化学研究的基本要求，八个醌 1 的晶体结构由 X 射线衍射确定。在具有 α 型堆积排列的 1a、1c、1e、1f、1i 和 1n 晶体中，乙烯基双键在对称中心具有短接触（< 4.4 A）。醌 1k 以 β 排列结晶，通过平移相关的分​​子之间的距离很短 (< 4.0 A)，并且在没有适当接触的情况下以γ 排列结晶。用紫外光照射所有醌1的晶体以进行[2+2]环加成。光反应性醌仅在乙烯基双键处二聚化，产生相应的环丁烷 9。形成了具有分子 Ci 对称性的二聚体 9a-9c、9e、9l-9n、9q、9r
• WATER-SOLUBLE COMPOSITION, PRODUCTION METHOD FOR CURED PRODUCT THEREOF, AND CURED PRODUCT THEREOF, AND ACYL PHOSPHINATE
  申请人：ADEKA CORPORATION

  公开号：US20200032021A1

  公开（公告）日：2020-01-30

  Provided are: a water-soluble composition which has excellent storage stability and is adaptable to a wide range of light sources and capable of forming a highly fine pattern; a method of producing a cured product of the same; a cured product of the same; and an acylphosphinate. The water-soluble composition contains: an acylphosphinate (A) represented by Formula (I) below, wherein X 1 represents an aryl group having 6 to 15 carbon atoms; X 2 represents a linear alkyl group having 1 to 8 carbon atoms or the like; A m+ represents an alkali metal ion or the like; and m represents a number of 1 to 3; and a compound (B) having a group represented by Formula (II) below, wherein R 1 represents a hydrogen atom or the like; Z 1 represents an oxygen atom or the like; R 2 represents a hydrogen atom or the like; Z 2 represents an alkylene group having 1 to 6 carbon atoms; n represents a number of 0 to 30; * means a bond; and, when the compound (B) has plural groups represented by Formula (II), plural R 1′ s, Z 1′ s, Z 2′ s and n's are each optionally the same or different.

  提供了以下内容：一种水溶性组合物，具有优异的储存稳定性，适用于广泛的光源，并能形成高度精细的图案；一种制备该固化产品的方法；一种该固化产品；以及一种酰基膦酸酯。水溶性组合物包含：由下式（I）表示的酰基膦酸酯（A），其中X1表示具有6到15个碳原子的芳基基团；X2表示具有1到8个碳原子的线性烷基基团或类似物；Am+表示碱金属离子或类似物；m表示1到3的数字；以及具有下式（II）表示的基团的化合物（B），其中R1表示氢原子或类似物；Z1表示氧原子或类似物；R2表示氢原子或类似物；Z2表示具有1到6个碳原子的烷基基团；n表示0到30的数字；*表示一个键；当化合物（B）具有由式（II）表示的多个基团时，多个R1'、Z1'、Z2'和n'可以是任意相同或不同。