4,4-dimethyl-2-<2-(2-methylphenyl)phenyl>-1,3-oxazoline | 156641-63-3

• 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: 4,4-dimethyl-2-<2-(2-methylphenyl)phenyl>-1,3-oxazoline
• 英文别名: Oxazole, 4,5-dihydro-4,4-dimethyl-2-(2'-methyl[1,1'-biphenyl]-2-yl)-；4,4-dimethyl-2-[2-(2-methylphenyl)phenyl]-5H-1,3-oxazole
• CAS: 156641-63-3
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: JRMDFPRKYDMTSY-UHFFFAOYSA-N

物化性质

• 沸点：
  393.1±21.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-<2-(2-methylphenyl)phenyl>-1,3-oxazoline 在 盐酸 、 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2-甲基-2'-[羟基(苯基)甲基]联苯
  参考文献：
  名称：

  Intramolecular reactivity of arylcarbenes: Biphenyl-2-ylcarbenes

  摘要：

  Biphenyl-2-ylcarbenes, 2-ArC(6)H(4)CR, were generated photolytically and thermally from diazo precursors. Cyclization, leading to fluorenes, competes with capture of the carbenes by methanol but proceeds faster than intramolecular hydrogen shifts (with R = Me) and intermolecular C-H insertion reactions (with R = H in cyclohexane). By comparison of product ratios with kinetic data for related carbenes from the literature, the cyclization rate is estimated as ca 10(11) s(-1). The intramolecular reactivity of biphenyl-2-ylcarbenes is nor significantly attenuated by variation of R (R = H, Me, Ph). Very minor effects of triplet sensitization and methanol quenching indicate that fluorenes arise from spin-equilibrated biphenyl-2-ylcarbenes, presumably from the singlet state. When Ar = mesityl, the carbene predominantly inserts into C-H bonds of the 2'-methyl groups, giving rise to a dihydrophenanthrene. Formation of a fluorene derivative, by formal insertion into C-C bonds, occurs as a minor process. This unprecedented reaction points to intervention of an o-xylylene in which the methyl group migrates. Laser flash photolysis (LFP) of 2-PhC(6)H(4)CN(2)Ph generates a transient absorption which is due to the T-0-->T-n transition of 9-phenylfluorene rather than to the presumed o-xylylene. On LFP of 2-ArC(6)H(4)CN(2)Ph in trifluoroethanol-acetonitrile, protonation of the carbenes gives rise to carbocations, 2-ArC(6)H(4)CH(+)Ph. The transient absorption spectra of these cations are strongly influenced by twisting about the Ar-Ar bond (Ar = Ph < o-tolyl < mesityl) whereas the rates of nucleophilic capture vary only slightly. Biphenyl-2-ylcarbenium ions (Ar = R = Ph) cyclize more slowly than the analogous carbenes, by a factor of greater than or equal to 10(4).

  DOI：

  10.1002/(sici)1099-1395(199609)9:9<598::aid-poc825>3.0.co;2-l
• 作为产物：
  描述：

  (2-methylphenyl)lithium 、 2-(2-氯苯基)-4,4-二甲基-4,5-二氢-1,3-恶唑 以 乙醚 为溶剂， 反应 1.0h， 以56%的产率得到4,4-dimethyl-2-<2-(2-methylphenyl)phenyl>-1,3-oxazoline
  参考文献：
  名称：

  活化的芳基氯与芳基锂和芳基格氏试剂的未催化偶联

  摘要：

  当与芳基锂试剂或芳基格氏试剂反应时，将2-（2-氯苯基）-4，4-二甲基-2-恶唑啉中的氯取代成联芳基。与格氏试剂的反应在与先前报道的锰催化方法相似的条件下进行。与锂试剂的反应虽然并不总是提供比格利雅试剂更大的产物收率，但反应时间和收率却要短得多，与从相应的氟衍生物获得的收率相当。

  DOI：

  10.1016/j.tetlet.2004.08.003

文献信息

• Synthesis and Characterization of Orally Active Nonpeptide Vasopressin V2 Receptor Antagonists.
  作者：Takehiko OHKAWA、Tatsuya ZENKOH、Masayuki TOMITA、Naomi HOSOGAI、Keiji HEMMI、Hirokazu TANAKA、Hiroyuki SETOI

  DOI：10.1248/cpb.47.501

  日期：——

  novel series of 2,6-diaza-5-oxobicyclo[5.4.0]undeca-1(7),8,10-triene derivatives exhibited antagonistic activity for vasopressin V1 and V2 receptors. Most of these compounds were synthesized and showed a high affinity potential for V2 receptor and low to moderate affinity potential for V1 receptor. The most potent and V2-selective compound, N-[4-[2,6-diaza-6-[2-(4-methylpiperazinyl)-2-oxoethyl] -5- oxobicyclo[5

  进行本研究以评估新系列的2,6-二氮杂-5-氧代双环[5.4.0] undeca-1（7），8,10-三烯衍生物是否表现出对血管加压素V1和V2受体的拮抗活性。这些化合物大多数都是合成的，对V2受体显示出高亲和力，对V1受体显示出低至中等的亲和力。最有效和V2选择性的化合物N- [4- [2,6-二氮杂-6- [2-（4-甲基哌嗪基）-2-氧代乙基] -5-氧代双环[5.4.0] undeca-1（7 ），8,10-三烯-2-基]-羰基]苯基1] [2-（4-甲基苯基）苯基]-甲酰胺（11b），对V2受体表现出2.9 nM的IC50，对于V1受体表现出200 nM的IC50 ， 分别。当对大鼠口服给药时，11b与对照大鼠相比，尿量增加了约18倍。
• US4220778A
  申请人：——

  公开号：US4220778A

  公开（公告）日：1980-09-02
• Intramolecular reactivity of arylcarbenes: Biphenyl-2-ylcarbenes
  作者：Michael Dorra、Klaus Gomann、Michael Guth、Wolfgang Kirmse

  DOI：10.1002/(sici)1099-1395(199609)9:9<598::aid-poc825>3.0.co;2-l

  日期：1996.9

  Biphenyl-2-ylcarbenes, 2-ArC(6)H(4)CR, were generated photolytically and thermally from diazo precursors. Cyclization, leading to fluorenes, competes with capture of the carbenes by methanol but proceeds faster than intramolecular hydrogen shifts (with R = Me) and intermolecular C-H insertion reactions (with R = H in cyclohexane). By comparison of product ratios with kinetic data for related carbenes from the literature, the cyclization rate is estimated as ca 10(11) s(-1). The intramolecular reactivity of biphenyl-2-ylcarbenes is nor significantly attenuated by variation of R (R = H, Me, Ph). Very minor effects of triplet sensitization and methanol quenching indicate that fluorenes arise from spin-equilibrated biphenyl-2-ylcarbenes, presumably from the singlet state. When Ar = mesityl, the carbene predominantly inserts into C-H bonds of the 2'-methyl groups, giving rise to a dihydrophenanthrene. Formation of a fluorene derivative, by formal insertion into C-C bonds, occurs as a minor process. This unprecedented reaction points to intervention of an o-xylylene in which the methyl group migrates. Laser flash photolysis (LFP) of 2-PhC(6)H(4)CN(2)Ph generates a transient absorption which is due to the T-0-->T-n transition of 9-phenylfluorene rather than to the presumed o-xylylene. On LFP of 2-ArC(6)H(4)CN(2)Ph in trifluoroethanol-acetonitrile, protonation of the carbenes gives rise to carbocations, 2-ArC(6)H(4)CH(+)Ph. The transient absorption spectra of these cations are strongly influenced by twisting about the Ar-Ar bond (Ar = Ph < o-tolyl < mesityl) whereas the rates of nucleophilic capture vary only slightly. Biphenyl-2-ylcarbenium ions (Ar = R = Ph) cyclize more slowly than the analogous carbenes, by a factor of greater than or equal to 10(4).
• Uncatalysed coupling of an activated aryl chloride with aryllithium and aryl Grignard reagents
  作者：Demet Astley、Hava Saygı、Sibel Gezer、Stephen T. Astley

  DOI：10.1016/j.tetlet.2004.08.003

  日期：2004.9

  afford biaryls occurs upon reaction with either aryllithium reagents or aryl Grignard reagents. The reactions with Grignard reagents occur under similar conditions to a previously reported manganese-catalysed procedure. The reactions with lithium reagents, whilst not always affording greater yields of product than the Grignard reagents, involve much shorter reaction times and afford yields, which are

  当与芳基锂试剂或芳基格氏试剂反应时，将2-（2-氯苯基）-4，4-二甲基-2-恶唑啉中的氯取代成联芳基。与格氏试剂的反应在与先前报道的锰催化方法相似的条件下进行。与锂试剂的反应虽然并不总是提供比格利雅试剂更大的产物收率，但反应时间和收率却要短得多，与从相应的氟衍生物获得的收率相当。