(+/-)-(E)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene) | 4825-70-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (+/-)-(E)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene)
• 英文别名: (E)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene)；1,3-bis-(4'-methoxyphenyl)penta-1,4-diene；(+/-)-Di-O-methylhinokiresinol；dimehtylhinokiresinol；Dihydrohinokiresinoldimethylether；(+/-)-Dimethyl-hinokiresinol；1-methoxy-4-[(1E)-1-(4-methoxyphenyl)penta-1,4-dien-3-yl]benzene
• CAS: 4825-70-1；96895-26-0；22338-49-4
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: JFPWOMOGZNTYSH-VMPITWQZSA-N

物化性质

• 沸点：
  418.2±33.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4’-二甲氧基查耳酮 在 盐酸 、 sodium tetrahydroborate 、 copper(l) iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 24.17h， 生成 (+/-)-(E)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene)
  参考文献：
  名称：

  Synthesis of norlignans and in vitro inhibitory activity of antigen-induced degranulation

  摘要：

  The synthesis and biological evaluation of a series of novel norlignans are described. Norlignans were evaluated for their inhibitory activity on the release of beta-hexosaminidase, a marker of degranulation, from RBL-2H3 cells induced by the IgE-antigen complex. The results showed that norlignans 4c and 4e potently inhibited degranulation, with IC50 values of 18.3 and 17.9 mu M, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.033

文献信息

• Enantioselective total synthesis of the di-O-methyl ethers of (–)-agatharesinol, (+)-hinokiresinol and (–)-sugiresinol, characteristic norlignans of Coniferae
  作者：Osamu Muraoka、Bao-Zhong Zheng、Noriyuki Fujiwara、Genzoh Tanabe

  DOI：10.1039/p19960000405

  日期：——

  enantioselective syntheses of the di-O-methyl ethers of the norlignans, (–)-agatharesinol (–)-1a, (+)-hinokiresinol (+)-2a and (–)-sugiresinol (–)-3a are described. Grignard addition of vinylmagnesium bromide to an aldimine (–)-13, prepared from the tert-butyl ester 11 and 4-methoxycinnamaldehyde 12, afforded a homochiral vinyl aldehyde, (–)-3-(4-methoxyphenyl)pent-4-enal (–)-14 in >95% ee, which was converted

  描述了降冰片聚糖，（-）-agatharesinol（-）-1a，（+）-hinokiresinol（+）-2a和（-）-sugiresinol（-）-3a的二-O-甲基醚的简便对映选择性合成。在叔丁酯11和4-甲氧基肉桂醛12制备的醛亚胺（–）-13中，将乙烯基溴化镁进行格利雅（Grignard）加成，得到均手性乙烯基醛（-）-3-（4-甲氧基苯基）戊-4-烯醛（–）-14的ee大于95％，通过第二次Grignard反应，将其转化为1,3-双（4-甲氧基苯基）戊-4-烯-1-醇（3 R）-6的非对映异构体混合物4-甲氧基苯基溴化镁。乙烯醇（3 R）-6的Sharpless'不对称二羟基化非对映选择性进行，得到所需的相对立体化学三醇（2 S，3 S）-7。此，在脱水时，得到（ - ） -二- Ö -methylsugiresinol（ - ） - 3b中，其中随后的酸催化的环化反应，得到（
• Ameer, Farouk; Drewes, Siegfried E.; Drewes, Mark W., Journal of the Chemical Society. Perkin transactions I, 1988, p. 1425 - 1430
  作者：Ameer, Farouk、Drewes, Siegfried E.、Drewes, Mark W.、Roos, Gregory H. P.、Watson, Martin C.

  DOI：——

  日期：——
• Practical Synthesis of (±)-Nyasol
  作者：Yuanying Fang、Haeil Park

  DOI：10.1080/00397911.2014.954729

  日期：2015.1.2

  A practical total synthesis of racemic nyasol (7) was explored. The -hydroxyketo compound 3 was prepared from commercially available starting materials in two steps. Chelation-controlled reduction of the -hydroxyketo compound 3 with Zn(BH4)(2) gave the anti-1,2-diol compound 4 as the major product (anti/syn=11.5:1). Stereospecific elimination reaction of a 1,3-cyclic thionocarbonate intermediate (5) exclusively yielded the Z-alkene compound 6. Our total synthesis is very concise (seven steps), uses commercially available starting materials, and offers good overall yield (40%).