3-羟基-2-甲基-3,3-二苯基-丙腈 | 6275-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-羟基-2-甲基-3,3-二苯基-丙腈
• 英文名称: 3-hydroxy-2-methyl-3,3-diphenyl-propionitrile
• 英文别名: (+/-)-3-Hydroxy-2-methyl-3.3-diphenyl-propionsaeure-nitril；3-Hydroxy-2-methyl-3,3-diphenylpropanenitrile
• CAS: 6275-86-1
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: NVXKKAKSNWELHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-羟基-2-甲基-3,3-二苯基-丙腈 在 乙醚 、 硫酸 、 溶剂黄146 作用下， 生成 2-methyl-1,1,5,5-tetraphenyl-penta-1,4-dien-3-one-imine
  参考文献：
  名称：

  Chodkiewicz et al., Bulletin de la Societe Chimique de France, 1958, p. 1586,1589

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯甲酮 、 丙腈 在 正丁基锂 、 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以66%的产率得到3-羟基-2-甲基-3,3-二苯基-丙腈
  参考文献：
  名称：

  氯化铈（III）介导的腈醇醛缩醛反应：使用手性有机铈配合物提高了非对映选择性

  摘要：

  已经发现将无水氯化铈添加到腈醛醇醛缩醛反应中可以提供高产率的β-羟基腈。另外，在氯化铈的存在下，α，β-不饱和羰基化合物与腈烯醇盐的醛醇缩合反应仅以良好的至优异的产率提供1、2加成。R-（+）-1,1'-bi-2-萘酚的有机铈配合物已成功地介导了硫醇烷基和芳基乙腈与醛的醛醇加成反应，该反应以良好的收率和中等至良好的非对映选择性提供了β-羟基腈。

  DOI：

  10.1016/s0040-4020(98)00122-7

文献信息

• Metal exchange between an electrogenerated organonickel species and zinc halide: application to an electrochemical, nickel-catalyzed Reformatsky reaction
  作者：Annie Conan、Soline Sibille、Jacques Perichon

  DOI：10.1021/jo00006a012

  日期：1991.3

  The mechanism of the electroreductive coupling of alpha-chloro esters or alpha-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques. The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the alpha-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent. The electrosynthesis of various beta-hydroxy esters, beta-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.
• Lettre; Meiners; Wichmann, Naturwissenschaften, 1946, vol. 33, p. 158
  作者：Lettre、Meiners、Wichmann

  DOI：——

  日期：——
• Lettre; Wick, Justus Liebigs Annalen der Chemie, 1957, vol. 603, p. 189,196
  作者：Lettre、Wick

  DOI：——

  日期：——
• Synthesis and histamine H2 agonistic activity of arpromidine analogues: replacement of the pheniramine-like moiety by non-heterocyclic groups
  作者：A Buschauer、A Friese-Kimmel、G Baumann、W Schunack

  DOI：10.1016/0223-5234(92)90145-q

  日期：1992.6

  Analogues of the potent histamine H-2 agonist arpromidine, characterized by non-heterocyclic groups (phenyl, cyclo-hexyl, alkyl) instead of the pheniramine-like portion, were prepared and tested for their H-2 agonistic and H-1 antagonistic activity in the isolated guinea pig right atrium and ileum, respectively. In the diphenylpropylguanidine series an increase in H-2 agonistic potency resulted from mono- or difluorination at one or both phenyl rings in the meta and/or para position (pD2 less-than-or-equal-to 7.75 vs pD2 = 7.15 for the unsubstituted parent compound). Compounds chlorinated at both phenyl rings were considerably less potent. Highest combined H-2 agonistic/H-1 antagonistic potency was found in the 4-fluorophenyl series. The arpromidine analogue with cyclohexyl and methyl group instead of phenyl and pyridine ring proved to be 30 times more potent than histamine in the atrium. The H-1 antagonistic potency in cyclohexyl compounds was lower than in the diaryl series. Thus, aromatic rings appear not to be required for high H-2 agonistic potency but are useful for combined H-2 agonistic/H-1 antagonistic activity.
• THOMAS R. C., J. LABELLED COMPOUNDS AND RADIOPHARM., 1978, 15, 591-597
  作者：THOMAS R. C.

  DOI：——

  日期：——