3,3-di-p-tolylacrylonitrile | 142669-91-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3-di-p-tolylacrylonitrile
• 英文别名: 3,3-Bis(4-methylphenyl)acrylonitrile；3,3-bis(4-methylphenyl)prop-2-enenitrile
• CAS: 142669-91-8
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: BXRLPSLCOXGWIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-di-p-tolylacrylonitrile 在 lithium aluminium tetrahydride 、 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 3,3-Bis(4-methylphenyl)propan-1-amine
  参考文献：
  名称：

  银催化芳基从碳中心到氮中心的长距离迁移

  摘要：

  据报道，惰性 CC 键的选择性裂解，然后通过银催化从碳到氮中心的长距离芳基迁移形成 CO/N 键。迁移产物很容易转化为定量产率的 γ-羟基胺和四氢喹啉衍生物。初步的机理研究表明了一种激进的途径。

  DOI：

  10.1021/jacs.5b10267
• 作为产物：
  描述：

  3,3-bis(4-methylphenyl)-2-propenal 在 O-(4-(trifluoromethyl)benzoyl)hydroxylamine 、 三氟乙酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 31.0h， 以75%的产率得到3,3-di-p-tolylacrylonitrile
  参考文献：
  名称：

  Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source

  摘要：

  The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and alpha,beta-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.

  DOI：

  10.1021/acs.orglett.5b02547

文献信息

• Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles
  作者：Qi Zhang、Linjing Zhang、Chaojun Tang、Huan Luo、Xuediao Cai、Yonghai Chai

  DOI：10.1016/j.tet.2016.09.010

  日期：2016.11

  We have developed an easy and practical method for the synthesis of α,β-unsaturated oximes and nitriles from readily available propargylic alcohols with hydroxylamine hydrochloride (NH2OH·HCl) under metal-free conditions. By using or not using p-toluenesulfonyl chloride (p-TsCl) as the dehydrating promoter, the desired nitriles or oximes could be obtained, respectively via a three-step one-pot or two-step

  我们已经开发了一种简便实用的方法，可在无金属条件下，用容易得到的炔丙醇与盐酸羟胺（NH 2 OH·HCl）合成α，β-不饱和肟和腈。通过使用或不使用对甲苯磺酰氯（p -TsCl）作为脱水促进剂，可以分别通过三步一锅法或两步一锅法以中等至优异的产率获得所需的腈或肟。具有良好的功能组兼容性。
• Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols with Hydroxylamine Hydrochloride To Give α,β-Unsaturated Amides and Alkenyl Nitriles
  作者：Ya-Ping Han、Xian-Rong Song、Yi-Feng Qiu、Xin-Hua Hao、Jia Wang、Xin-Xing Wu、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/acs.joc.5b01633

  日期：2015.9.18

  β-unsaturated amides and alkenyl nitriles from readily available propargylic alcohols. The reaction proceeded smoothly under the neutral conditions with hydroxylamine hydrochloride (NH2OH·HCl) as the nitrogen source. The development of these new strategies has significantly extended the application of hydroxylamine hydrochloride to the chemistry of propargylic alcohols. Moreover, both secondary and tertiary alcohols

  我们已经开发出一种高度选择性的方法，可以从容易获得的炔丙醇中合成α，β-不饱和酰胺和烯基腈。在中性条件下，以盐酸羟胺（NH 2 OH·HCl）为氮源，反应平稳进行。这些新策略的发展极大地扩展了羟胺盐酸盐在炔丙醇化学中的应用。此外，仲醇和叔醇都已被高度区域选择性地转化为具有良好官能团相容性的所需产物。
• Ring-Splitting Reaction of 2,2-Diarylthietane by Electron-Transfer Photosensitization of 9,10-Dicyanoanthracene
  作者：Kensuke Shima、Akira Sazaki、Kenichi Nakabayashi、Masahide Yasuda

  DOI：10.1246/bcsj.65.1472

  日期：1992.5

  A 9,10-dicyanoanthracene (DCA)-photosensitized reaction of 3-cyano- or 3-ethoxy-2,2-diarylthietane in acetonitrile gave selectively 2-cyano- or 2-ethoxy-1,1-diarylethene. The ring-splitting reaction proceeds via a one-electron oxidation of the sulfur atom of thietane ring by a photochemical electron transfer to the excited singlet state of DCA.

  3-氰基-或3-乙氧基-2,2-二芳基硫杂环丁烷在乙腈中的9,10-二氰基蒽(DCA)-光敏反应选择性地产生2-氰基-或2-乙氧基-1,1-二芳基乙烯。开环反应通过硫杂环丁烷环的硫原子的单电子氧化进行，通过光化学电子转移到 DCA 的激发单线态。
• Synthesis of Acrylonitriles through an FeCl₃-Catalyzed Domino Propargylic Substitution/Aza-Meyer-Schuster Rearrangement Sequence
  作者：Lu Hao、Feng Wu、Zong-Cang Ding、Su-Xia Xu、Yan-Li Ma、Li Chen、Zhuang-Ping Zhan

  DOI：10.1002/chem.201200763

  日期：2012.5.21

  Nontoxic cyanide source: An unprecedented route to acrylonitriles by employing propargylic alcohols and para‐tolylsulfonohydrazide as a combined cyano source has been developed (see scheme). This efficient and practical cyanation reaction proceeds through an FeCl3‐catalyzed domino propargylic substitution/aza‐Meyer–Schuster rearrangement sequence, the rearrangement process of which is reported for

  无毒氰化物来源：通过使用炔丙醇和对甲苯磺酰磺酰肼作为组合氰化物来源，开发了一条通往丙烯腈的前所未有的途径（参见方案）。这种高效，实用的氰化反应是通过FeCl 3催化的多米诺炔丙基取代/氮杂-迈耶-舒斯特重排序列进行的，该重排过程是首次报道。
• Derivatives of urea and related diamines, methods for their manufacture, and uses therefor
  申请人：DePrez Pierre

  公开号：US20080125424A1

  公开（公告）日：2008-05-29

  The present invention relates generally to compounds represented in Formula I, pharmaceutical compositions comprising them and methods of treating of diseases or disorders related to the function of the calcium sensing receptor. The invention also relates to processes for making such compounds and to intermediates useful in these processes.

  本发明通常涉及式I所代表的化合物、包含它们的制药组合物以及治疗与钙感受受体功能相关的疾病或障碍的方法。本发明还涉及制备这些化合物的过程以及在这些过程中有用的中间体。