allylbenzene-d | 63523-01-3

• 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: allylbenzene-d
• 英文别名: 3-phenyl-1-propene-3-d1；(1-deuterio-allyl)-benzene；1-Deuterioprop-2-enylbenzene
• CAS: 63523-01-3
• 化学式: C₉H₁₀
• 分子量: 119.17
• InChiKey: HJWLCRVIBGQPNF-RAMDWTOOSA-N

物化性质

• 沸点：
  156 °C
• 密度：
  0.883±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  allylbenzene-d 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 iron(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以72%的产率得到trans-<β-2H>cinnamaldehyde
  参考文献：
  名称：

  Iron-facilitated direct oxidative C–H transformation of allyl arenes to alkenyl aldehydes

  摘要：

  A direct oxidative approach to alkenyl aldehydes from allyl arenes via allyl sp(3) C-H functionalization was disclosed. An inexpensive iron catalyst was employed to facilitate this transformation. The mechanistic studies indicate that the cleavage of the allyl sp(3) C-H bond is involved in the rate-determining step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.041
• 作为产物：
  描述：

  在 diclazuril 作用下， 以 重水 为溶剂， 生成 allylbenzene-d
  参考文献：
  名称：

  一种新的烯胺合成：腈与烯丙基化试剂的烯丙基化-氨基化反应

  摘要：

  烯丙基化试剂与某些在α位具有另一个吸电子基团的腈1的反应以高至良好的产率提供了相应的烯丙基化-氨基化产物2。

  DOI：

  10.1016/s0040-4039(98)00929-0

文献信息

• Unique catalysis of gold nanoparticles in the chemoselective hydrogenolysis with H2: cooperative effect between small gold nanoparticles and a basic support
  作者：Akifumi Noujima、Takato Mitsudome、Tomoo Mizugaki、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.1039/c2cc32850j

  日期：——

  Gold nanoparticles on hydrotalcite act as a heterogeneous catalyst for the chemoselective hydrogenolysis of various allylic carbonates to the corresponding terminal alkenes using H2 as a clean reductant. The combination of gold nanoparticles and basic supports elicited significantly unique and selective catalysis in the hydrogenolysis.

  金纳米颗粒在水滑石上作为异质催化剂，用于选择性氢解各种烯丙基碳酸盐，生成相应的末端烯烃，以H2作为清洁还原剂。金纳米颗粒与碱性载体的结合显著引发了独特的选择性氢解催化作用。
• Synthesis and reaction of (η5-pentamethylcyclopentadienyl)-bis(allyl)tantalum(III) complexes; crystal structure of Ta(η5-C5Me5)-(η3-1-phenylallyl)2
  作者：Kazushi Mashima、Yoshimichi Yamanaka、Yoshihiko Gohro、Akira Nakamura

  DOI：10.1016/0022-328x(93)80413-6

  日期：1993.8

  We report here the synthesis and X-ray structure of a mononuclear 16-electron (η5-pentamethylcyclopentadienyl)bis(allyl)-tantalum complex, Cp★Ta(η3-PhC3H4)2 (2). Carbonylation of 2 induced the coupling reaction with phenylallyl groups bound to tantalum to give 1,6-diphenyl-1,5-hexadiene and carbonyltantalum complexes. Oxidation of 2 with one-electron oxdidants, DDQ and TCNQ, gave the tantalum(IV) complexes

  我们在这里报告的单核的合成和X射线结构16电子（η 5 -五甲基）双（烯丙基）-tantalum复杂中，Cp★的Ta（η 3 -PhC 3 ħ 4）2（2）。2的羰基化诱导与结合到钽的苯基烯丙基的偶联反应，得到1,6-二苯基-1,5-己二烯和羰基钽配合物。用单电子氧化剂DDQ和TCNQ对2进行氧化，得到钽（IV）络合物[Cp★Ta（PhC 3 H 4）2] [氧化剂]。
• Iron-Facilitated Direct Oxidative C−H Transformation of Allylarenes or Alkenes to Alkenyl Nitriles
  作者：Chong Qin、Ning Jiao

  DOI：10.1021/ja1070202

  日期：2010.11.17

  facilitated by an inexpensive homogeneous iron catalyst. Three C-H bond cleavages occur under the mild conditions during this process. Mechanistic studies indicate that the cleavage of the allyl C(sp(3))-H bond is involved in the rate-determining step. This observation may provide an opportunity to achieve C(sp(3))-H functionalization catalyzed by an iron catalyst.

  本文描述了第一种直接从烯丙基芳烃或烯烃制备烯基腈的方法，该方法由廉价的均相铁催化剂促进。在此过程中，在温和条件下发生三个 CH 键断裂。机理研究表明烯丙基 C(sp(3))-H 键的断裂参与了速率决定步骤。这一观察结果可能为实现由铁催化剂催化的 C(sp(3))-H 功能化提供了机会。
• Ene Reaction of Arylallyl Alkenes with C₆₀. A Mechanistic Approach
  作者：Nikos Chronakis、Michael Orfanopoulos

  DOI：10.1021/ol990204o

  日期：1999.12.1

  [GRAPHICS]The ene reaction of arylallyl alkenes with C-60 occurs either by a concerted mechanism or by the reversible formation of a charged or a dipolar intermediate, followed by the C-H(D) breakage in a rate-limiting step.
• Allyl- and Benzylindium Reagents. Carboindation of Carbon−Carbon and Carbon−Nitrogen Triple Bonds
  作者：Naoya Fujiwara、Yoshinori Yamamoto

  DOI：10.1021/jo990160x

  日期：1999.5.1

  The reaction of unactivated simple terminal alkynes 1 with allylindiums in THF proceeded smoothly to give the corresponding allylation products 2 in good to high yields. This result is in marked contrast to that of the reaction carried out in DMF, where the allylation of unactivated alkynes was very sluggish. The allylic group of the reagent was attached to the internal carbon of the triple. bond, and indium was attached to the less substituted terminal carbon, except for the case of TMS substituted acetylenes 1j and 1k in which the allyl group went to the less substituted carbon of the triple band. The reaction of unactivated simple terminal and certain internal acetylenes with benzylindium in THF proceeded smoothly to afford the corresponding benzylation products 18 in good to high yields. The benzyl group was attached to the less substituted unhindered carbon of the triple bond, and indium was attached to the more sterically congested carbon. The reaction of activated nitriles 3 with allylindiums in THF at 70 degrees C gave the corresponding allylation-enamination products 4 in high to excellent yields. This reaction provides a useful method for the synthesis of highly functionalized enamines, which are not easily available via conventional methods. The mechanisms on the above three indation reactions are discussed.