(E)-4-Dimethylaminomethyl-1-phenyl-non-1-en-3-one; hydrochloride | 51469-43-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-Dimethylaminomethyl-1-phenyl-non-1-en-3-one; hydrochloride
• 英文别名: 4-((Dimethylamino)methyl)-1-phenyl-1-nonen-3-one hydrochloride；(E)-4-[(dimethylamino)methyl]-1-phenylnon-1-en-3-one;hydrochloride
• CAS: 51469-43-3
• 化学式: C₁₈H₂₇NO*ClH
• 分子量: 309.879
• InChiKey: YUGFIAAXUMXQFW-IERUDJENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-Dimethylaminomethyl-1-phenyl-non-1-en-3-one; hydrochloride 在 sodium hydroxide 作用下， 生成 (E)-4-Methylene-1-phenyl-non-1-en-3-one
  参考文献：
  名称：

  具有抗肿瘤特性的取代的4-二甲基氨基甲基-1-苯基-1-壬烯-3-酮的合成和物理性质。

  摘要：

  DOI：

  10.1002/jps.2600630117

文献信息

• Hydride Reductions of 1-Phenyl-1-nonen-3 -one: Mass Spectrometry of 1-Phenyl-1-nonen-3-ols and Relative Stereochemistry of the Diastereoisomeric 4-Dimethylaminomethyl-1-Phenyl-1-nonen-3-ols
  作者：Wesley Gordon Taylor、Jonathan Richard Dimmock

  DOI：10.1139/v74-368

  日期：1974.7.1

  The metal hydride reduction products of some styryl ketones and dimethylaminomethyl Mannich bases have been investigated. Sodium borohydride selectively attacked the carbonyl carbon atom to give the desired allylic alcohols. Reduction of 1-phenyl-1-nonen-3-one with lithium aluminum hydride gave 1-phenyl-3-nonanol which represents the conjugate addition product. Fragmentations of 1-phenyl-1-nonen-3-ol were compared to the modes of mass spectral breakdown of 4-phenyl-3-buten-2-ol, an allylic alcohol which is known to behave like a saturated ketone on electron bombardment. Peaks corresponding to the McLafferty ion and the loss of a methyl radical from this rearrangement product were observed. Certain Mannich bases were reduced to diastereoisomeric allylic amino alcohols. The separation, ¹H n.m.r. spectroscopy, and relative stereochemistry of the diastereoisomers are discussed.

  一些styryl酮和二甲氨基甲基Mannich碱的金属氢化物还原产物已经被研究。钠硼氢选择性地攻击羰基碳原子，形成所需的烯丙基醇。用铝锂氢还原1-苯基-1-壬烯-3-酮得到了1-苯基-3-壬醇，代表了共轭加成产物。将1-苯基-1-壬烯-3-醇的裂解与4-苯基-3-丁烯-2-醇的质谱断裂模式进行了比较，后者是已知在电子轰击下表现出像饱和酮的烯丙基醇。观察到与McLafferty离子和从这种重排产物中失去甲基自由基的峰相对应。某些Mannich碱被还原为对映异构的烯丙基氨基醇。讨论了对映异构体的分离、1H核磁共振光谱和相对立体化学。
• Dimmock, J.R.; Smith, L.M.; Smith, P.J., Canadian Journal of Chemistry, 1980, vol. 58, p. 984 - 991
  作者：Dimmock, J.R.、Smith, L.M.、Smith, P.J.

  DOI：——

  日期：——
• Synthesis and Physical Properties of Substituted 4-Dimethylaminomethyl-1-phenyl-1-nonen-3-ones Possessing Antitumor Properties
  作者：J.R. Dimmock、W.G. Taylor

  DOI：10.1002/jps.2600630117

  日期：1974.1