2-phenylpropene-1,1,3,3,3-d5 | 10378-58-2

• 英文名称: 2-phenylpropene-1,1,3,3,3-d5
• 英文别名: 1,1,3,3,3-pentadeuterio-2-phenylpropene；α-methylstyrene-d5；(prop-1-en-2-yl-d₅)benzene；(1,1,3,3,3-D5)-2-Phenyl-propen-(1)；(2,2-dideuterio-1-trideuteriomethyl-vinyl)-benzene；2-Phenylperdeuteropropen；1,1,3,3,3-Pentadeuterioprop-1-en-2-ylbenzene
• CAS: 10378-58-2
• 化学式: C₉H₁₀
• 分子量: 123.139
• InChiKey: XYLMUPLGERFSHI-KPAILUHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  1
• 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：

  2-phenylpropene-1,1,3,3,3-d5 在 cyclopentadienylchromiumtricarbonyl hydride 作用下， 以 氘代苯 为溶剂， 生成
  参考文献：
  名称：

  Kinetics of Hydrogen Atom Transfer from (η⁵-C₅H₅)Cr(CO)₃H to Various Olefins:  Influence of Olefin Structure

  摘要：

  Treating (eta(5)-(CH5)-H-5)Cr(CO)(3)H (1) or (eta(5)-C5H5) Cr(CO)(3)D (1-d(1)) with an excess of olefin containing the opposite isotope generally leads to H/D exchange, although hydrogenation is also observed in some cases. Application of an appropriate statistical correction to the observed exchange rate gives k(H) and k(D), the rate constants for H-center dot (D-center dot) transfer from (eta(5)-C5H5) Cr(CO)(3)H (D) to various olefins. The values of k(H) and k(D) vary appreciably with the substituents on the double bond. Phenyl-substituted olefins accept H-center dot more readily than do carbomethoxy-substituted olefins, although the latter accept H-center dot more readily than do alkyl-substituted olefins. A methyl substituent on the incipient radical site increases kH at 323 K by a factor between 5 and 50. A methyl substituent on the carbon to which the H-center dot is being transferred decreases k(H) substantially. On the whole, the rate constants for H-center dot transfer reflect steric effects as well as the stability of the resulting carbon-centered radicals.

  DOI：

  10.1021/ja066325i
• 作为产物：
  描述：

  1,1,1,3,3,3-hexadeuterio-2-phenyl-2-propanol 在 methyl N-(triethylammoniosulfonyl) carbamate 作用下， 以 苯 为溶剂， 以60%的产率得到2-phenylpropene-1,1,3,3,3-d5
  参考文献：
  名称：

  Photoaddition of alkenes to N-methyl-1,8-naphthalimide in methanol. Evidence for the mechanism of the formation of the tetracyclic adducts

  摘要：

  DOI：

  10.1021/jo00392a021

文献信息

• Photochemistry of some deoxybenzoins in micellar solutions. Cage effects, isotope effects, and magnetic field effects
  作者：Nicholas J. Turro、Jochen Mattay

  DOI：10.1021/ja00404a037

  日期：1981.7

  investigated. It was found that the extent of cage disproprotionation to yield benzaldehydes 6 and ..cap alpha..-methylstyrenes 7 is enhanced by a factor of about 10 compared to the photolyses in homogeneous organic solvents. The advantage of using micelles rather than homogeneous solutions to enhance the magnitude of magnetic isotope and magnetic field effects on cage disproportionation is demonstrated. The

  已经研究了 1,2-二苯基-2-甲基-1-丙酮 (1) 及其 D-、/sup 13/C- 和烷基取代衍生物 2 至 5 在各种胶束溶液中的光解作用。发现笼歧化产生苯甲醛 6 和..cap α..-甲基苯乙烯 7 的程度与均相有机溶剂中的光解相比提高了约 10 倍。证明了使用胶束而不是均匀溶液来增强磁同位素和磁场对笼歧化作用的大小的优势。结果被解释为一种机制，该机制涉及超精细诱导的三重自由基对 (/sup 3/RP) 的系统间交叉形成单线态自由基对 (/sup 1/RP) 和 /sup 3/ 逃逸之间的竞争来自胶束的 RP。
• Photochemistry of 1,2-diphenyl-2,2-dimethyl-propanone-1 in micellar solutions. Cage effects, isotope effects and magnetic field effects.
  作者：Nicholas J. Turro、Jochen Mattay

  DOI：10.1016/s0040-4039(00)92783-7

  日期：1980.1

  The cage reaction resulting from photolysis of PhCOC (CH3)2Ph and PhCOC(CD3)2Ph in micellar solution is shown to be subject to substantial magnetic field and magnetic isotope effects.

  由PhCOC（CH 3）2 Ph和PhCOC（CD 3）2 Ph在胶束溶液中的光解所引起的笼式反应显示出受到大量磁场和磁同位素效应的影响。
• Conformational dependence of isotope effects for hyperconjugating methyl groups. Nonadditivity of NMR isotope shifts in benzylic ions
  作者：David A. Forsyth、Peter Lucas、Robert M. Burk

  DOI：10.1021/ja00365a044

  日期：1982.1

  possible methyl conformations for partially deuterated methyl groups, so that each C-H(D) bond is not equally involved in hyperconjugation. This interpretation is supported by the observation of an isotope effect on the vicinal /sup 1/H-/sup 19/F coupling constant in the phenylmethylfluorcarbenium ion, PhCFCH/sub 3//sup +/.

  甲基中的氘取代导致苯基二甲基碳鎓离子的邻位和对位的 /sup 13/C NMR 信号的长程低场位移。在..cap α..-甲基基团氘化后，(p-氟苯基)碳鎓离子的/sup 19/F 信号中发生类似的低场同位素位移。这些 NMR 同位素位移类似于二次 ..β..-氘同位素对速率和平衡的影响，并产生于超共轭相互作用。用整个 CD/sub 3/ 基团取代 CH/sub 3/ 基团的效果是相加的，但甲基中氘取代的效果不是相加的。非加成行为归因于部分氘化甲基的可能甲基构象的数量不等，因此每个 CH(D) 键在超共轭中的参与程度不同。
• Solvolytic elimination reactions. Stepwise or concerted?
  作者：Xavier Creary、Vincent P. Casingal、Charlene E. Leahy

  DOI：10.1021/ja00058a018

  日期：1993.3

  lost exclusively when the elimination product forms. A concerted ester pyrolysis type of mechanism is therefore ruled out. The tertiary benzylic trifluoroacetate Ph(CH 3 )C(CONMe 2 )(OCOCF 3 ), 13, solvolyzes to give exclusively an elimination product. The β-CD 3 isotope effect on rate was 1.15. There is, however, a larger isotope effect (2.5) in formation of the elimination product when Ph(CH 2 D)C(CONMe

  2-Aryl-endo-2-norbornyl trifluoroacetates 11 溶剂分解得到很大一部分的氯化产物。氘标记研究表明，外氢仅在消除产物形成时丢失。因此排除了协同酯热解类型的机制。叔苄基三氟乙酸盐Ph(CH 3 )C(CONMe 2 )(OCOCF 3 ), 13 溶解以专门提供消除产物。β-CD 3 同位素对速率的影响为1.15。然而，当 Ph(CH 2 D)C(CONMe 2 )(OCOCF 3 ) 溶解时，消除产物的形成过程中存在较大的同位素效应 (2.5)
• Functionalization of Alkenyl C–H Bonds with D2O via Pd(0)/Carboxylic Acid Catalysis
  作者：Giovanni Maestri、Nicola Camedda、Andrea Serafino、Raimondo Maggi、Franca Bigi、Gianpiero Cera

  DOI：10.1055/s-0039-1690892

  日期：2020.6

  method for the extensive labeling of alkenyl C–H bonds through the combination of a palladium(0) complex and a carboxylic acid in the presence of deuterium oxide. The reaction can be applied to a variety of terminal alkenes and the best results are obtained with aryl-substituted examples. This method represents a convenient approach for the preparation of extensively labeled chemicals from the cheapest

  我们在此报告了一种简单的催化方法，用于在氘化氧存在下，通过钯（0）配合物和羧酸的结合来广泛标记烯基CH键。该反应可用于各种末端烯烃，用芳基取代的实例可获得最佳结果。该方法代表了从最便宜和最安全的氘源制备带有广泛标记的化学药品的便捷方法。