(E)-4,4-dimethyl-5-phenylpent-2-ene | 113460-11-0

• 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)-4,4-dimethyl-5-phenylpent-2-ene
• 英文别名: [(E)-2,2-dimethylpent-3-enyl]benzene
• CAS: 113460-11-0
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: DBPWYJUESMHZEN-ONNFQVAWSA-N

物化性质

• 沸点：
  231.0±10.0 °C(Predicted)
• 密度：
  0.878±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (E)-4,4-dimethyl-5-phenylpent-2-ene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以96%的产率得到trans-1-(1,1-dimethyl-2-phenylethyl)-2-methyloxirane
  参考文献：
  名称：

  Substituent effects and the Wittig mechanism: the case of stereospecific oxaphosphetane decomposition

  摘要：

  DOI：

  10.1021/ja00220a036
• 作为产物：
  描述：

  (3R)-2,2,2-triethyl-3-methyl-3-(2-methyl-1-phenylpropan-2-yl)-1,2λ5-oxaphosphetane 生成 (E)-4,4-dimethyl-5-phenylpent-2-ene
  参考文献：
  名称：

  VEDEJS, E.;MARTH, C. F.;RUGGERI, R., J. AMER. CHEM. SOC., 110,(1988) N 12, 3940-3948

  摘要：

  DOI：

文献信息

• DBP ylides: Wittig reagents for synthesis of E-alkenes from aldehydes
  作者：E. Vedejs、C. Marth

  DOI：10.1016/s0040-4039(00)96322-6

  日期：——

  Phosphorus ylides based on the dibenzophosphole (DBP) ring system convert aldehydes into trans-disubstituted oxaphosphetanes with good to excellent selectivity. Decomposition at 70–110° affords alkenes with E:Z ratios from 6:1 to > 100:1.

  基于二苯并磷腈（DBP）环系统的磷化磷化物可将醛转化为具有良好或优异的选择性的反式二取代的氧杂膦酸酯。在70–110°分解可得到E：Z比为6：1至> 100：1的烯烃。
• Stereochemistry of Carbenic 1,2-Vinyl Shifts
  作者：Wolfgang Kirmse、Siegfried Kopannia

  DOI：10.1021/jo971691t

  日期：1998.2.1

  Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R'CH=CHC(Ph)=CR2, were found to predominate over gamma-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R' = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R' = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point, to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).
• A bridged tetrahydrophosphole ylide derived from 9-phenylphosphabicyclo[4.2.1]nonane: a reagent for E-selective Wittig reactions
  作者：E. Vedejs、M. J. Peterson

  DOI：10.1021/jo00060a001

  日期：1993.4

  The bicyclic ylide 4 reacts with aldehydes to afford the E-alkenes. Selectivity is 94-6% E for unbranched aldehydes, but the selectivity decreases with increasing alpha-branching. Ylide 4 is the first E-selective, nonstabilized ylide that allows efficient utilization of the P-alkyl substituent.
• Mechanism of the Wittig reaction: the role of substituents at phosphorus
  作者：E. Vedejs、C. F. Marth

  DOI：10.1021/ja00220a037

  日期：1988.6
• VEDEJS, E.;MARTH, C. F.;RUGGERI, R., J. AMER. CHEM. SOC., 110,(1988) N 12, 3940-3948
  作者：VEDEJS, E.、MARTH, C. F.、RUGGERI, R.

  DOI：——

  日期：——