(E)-((cinnamyloxy)methylene)dibenzene | 14326-45-5

• 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)-((cinnamyloxy)methylene)dibenzene
• 英文别名: trans-Cinnamyl-diphenylmethyl-aether；[(E)-3-benzhydryloxyprop-1-enyl]benzene
• CAS: 14326-45-5
• 化学式: C₂₂H₂₀O
• 分子量: 300.4
• InChiKey: XNWOBSLUELUDES-JLHYYAGUSA-N

物化性质

• 沸点：
  442.1±24.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二苯甲醇 、 丙-1,2-二烯基苯 在 四(三苯基膦)钯 苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以75%的产率得到(E)-((cinnamyloxy)methylene)dibenzene
  参考文献：
  名称：

  Pd(0)–PhCOOH catalyzed addition of oxygen pronucleophiles to allenes and internal alkynes

  摘要：

  我们已经开发了一个催化系统，利用5 mol％ Pd（PPh3）4和10 mol％苯甲酸的组合，实现了醇类对烯烃的加成。同样，描述了羧酸对炔烃的加成反应。在所有情况下，反应进行良好，产率高，产物的区域和立体选择性高。关键词：加成，醇类，羧酸，烯烃，炔烃，钯。

  DOI：

  10.1139/v05-043

文献信息

• Pyrolysis of allyl ethers. Unimolecular fragmentation to propenes and carbonyl compounds
  作者：R. C. Cookson、S. R. Wallis

  DOI：10.1039/j29660001245

  日期：——

  about 500° allyl ethers undergo decomposition through a cyclic, six-atom transition state with transfer of a hydrogen atom to give high yields of a carbonyl compound and a propene, in which the double bond has moved from the 2,3- to the 1,2-position of the allyl system. The rate of reaction is rather insensitive to structural variation in either the allyl or alkyl part of the ether. Allyl α-deuterodiphenylmethyl

  在约500°的气相中，烯丙基醚通过六原子的环状过渡态分解并转移氢原子，从而高产率地获得了羰基化合物和丙烯，其中双键已从2处移出3-烯丙基系统的1,2-位置。反应速率对醚的烯丙基或烷基部分的结构变化不敏感。烯丙基α-氘代二苯甲基醚的反应仅比未氘代化合物慢约10％。
• Palladium/benzoic acid-catalyzed hydroalkoxylation of alkynes
  作者：Isao Kadota、Leopold Mpaka Lutete、Akinori Shibuya、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(01)01207-2

  日期：2001.8

  The reaction of the internal alkyne 1 with alcohols 2 in the presence of a catalytic amount of Pd(PPh3)4 and benzoic acid in dioxane at 100°C gave the allylic ethers 3 in good to high yields. The reaction proceeds via the palladium/benzoic acid-catalyzed isomerization of the alkyne 1 to allene 6, followed by the addition of alcohols 2 to the π-allylpalladium intermediate 7 formed by the hydropalladation

  内部炔烃1与醇2在催化量的Pd（PPh 3）4和苯甲酸在二恶烷中在100℃下的反应以良好或高收率得到烯丙基醚3。该反应通过炔烃1的钯/苯甲酸催化的异构化为丙二烯6而进行，然后将醇2加到通过将所得的丙二烯6进行加氢钯制反应而形成的π-烯丙基钯中间体7中。。此外，在碳链末端具有羟基的炔烃的分子内反应以良好的产率得到了五元和六元环状醚。
• Benzyl C–O and C–N Bond Construction via C–C Bond Dissociation of Oxime Ester under Visible Light Irradiation
  作者：Xiuwei Fan、Tao Lei、Zan Liu、Xiu‐Long Yang、Yuan‐Yuan Cheng、Ge Liang、Bin Chen、Chen‐Ho Tung、Li‐Zhu Wu

  DOI：10.1002/ejoc.201901060

  日期：2020.3.15

  A photoredox benzyl activation was developed via formidable C(sp3)–C(sp3) bond dissociation of 1‐aryl acetone oxime esters, easily prepared from benzyl ketones. The generated benzyl cation coupling with diverse O‐ and N‐ nucleophiles successfully forged important benzyl ether and amines derivatives that are valuable in last‐stage functionalizations.

  光氧化还原苄基活化是通过1-芳基丙酮肟酯的强C（sp 3）–C（sp 3）键解离作用而开发的，该酯易于从苄基酮制备。生成的苄基阳离子与各种O-和N-亲核试剂偶联成功地锻造了重要的苄基醚和胺衍生物，这些衍生物在最后阶段的功能化中很有价值。
• Palladium-catalyzed coupling of alkynes with alcohols and carboxylic acids
  作者：Weijiang Zhang、Anthony R. Haight、Margaret C. Hsu

  DOI：10.1016/s0040-4039(02)01436-3

  日期：2002.9

  The palladium-catalyzed coupling of alkynes with alcohols and carboxylic acids to give allylic ethers and esters has been achieved. With phenols, these conditions furnish the C-alkylation products. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Pd(0)–PhCOOH catalyzed addition of oxygen pronucleophiles to allenes and internal alkynes
  作者：Nitin T Patil、Nirmal K Pahadi、Yoshinori Yamamoto

  DOI：10.1139/v05-043

  日期：2005.6.1

  We have developed a catalytic system that enables the addition of alcohols to allenes using a combination of 5 mol% Pd(PPh₃)₄ and 10 mol% benzoic acid. Likewise, the addition reaction of carboxylic acids to alkynes is described. In all cases the reaction proceeded well, giving the corresponding allylation products in good-to-high yields with high regio- and stereoselectivities.Key words: addition, alcohols, carboxylic acids, allenes, alkynes, palladium.

  我们已经开发了一个催化系统，利用5 mol％ Pd（PPh3）4和10 mol％苯甲酸的组合，实现了醇类对烯烃的加成。同样，描述了羧酸对炔烃的加成反应。在所有情况下，反应进行良好，产率高，产物的区域和立体选择性高。关键词：加成，醇类，羧酸，烯烃，炔烃，钯。