(+/-)-2-dimethylamino-3-pentanone | 71504-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-2-dimethylamino-3-pentanone
• 英文别名: (R,S)-2-dimethylamino-3-pentanone；2-dimethylamino-pentan-3-one；2-Dimethylamino-pentan-3-on；2-(dimethylamino)pentan-3-one
• CAS: 71504-23-9
• 化学式: C₇H₁₅NO
• 分子量: 129.202
• InChiKey: LCCONZUJEGTUSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-dimethylamino-3-pentanone 在 sodium hydride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成 Toluene-4-sulfonate1,1,2,4-tetramethyl-3-oxo-2,3-dihydro-1H-pyrrolium;
  参考文献：
  名称：

  环状酮烯基铵盐的合成与性能

  摘要：

  环状酮链烯基铵盐（4）–（8）是通过较短的一般路线制备的，并已对其酸性和亲电性质进行了研究。

  DOI：

  10.1039/c39870001288
• 作为产物：
  描述：

  2-溴-3-戊酮 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (+/-)-2-dimethylamino-3-pentanone
  参考文献：
  名称：

  On the enantiomers of 2-dimethylamino-3-pentanone, key intermediates in the synthesis of analgesic alkylaminoalkylnaphthalenes

  摘要：

  2-Dimethylamino-3-pentanone 1 is the key intermediate in the synthesis of alkylaminoalkylnaphthalenic analgesics. In this paper the resolution of this compound with L- and D-dibenzoyltartaric acids is described. The behavior of the diastereomeric dibenzoyltartrates and of the enantiomers in solution is investigated by NMR spectroscopy, polarimetry and chiral gas-chromatographic analysis. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00223-2

文献信息

• 387. Action of the grignard reagent upon aminonitriles. Part II
  作者：Thomas Thomson、Thomas S. Stevens

  DOI：10.1039/jr9320002607

  日期：——
• JUNG, MICHAEL E.;LOVE, BRIAN E., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 17, 1288-1290
  作者：JUNG, MICHAEL E.、LOVE, BRIAN E.

  DOI：——

  日期：——
• Dialkylaminoalkylnaphthalenes as novel opioid-like analgesics
  作者：Simona Collina、Ornella Azzolina、Dina Vercesi、Francesca Benevelli、Athos Callegari、Carla Tadini、Enrica Lanza、Annalisa Barbieri、Victor Ghislandi

  DOI：10.1016/s0968-0896(00)00011-0

  日期：2000.4

  The study of dialkylaminoalkylnaphthalenes as novel opioid-like analgesics is reported. In particular, the synthesis of (IX,2R/1S,2S)-1-ethyl-1-[2-(6-hydroxynaphthyl)]-1-hydroxy-2-methyl-2-dimethylaminoethane and its structural analogue (1R,2R/1S,2S)-1-ethyl-1-[2-(6-fluoronaphthyl)]-1-hydroxy-2-methyl-2-dimethylaminoethane and the configurational analysis by X-ray and H-1 NMR spectroscopy are described. Pharmacological profiles are discussed on the basis of the experimental results of analgesia tests (hot plate and writhing test) and rota-rod test, which was performed to distinguish analgesia from drug-induced motor changes. The compounds showed dose-dependent antinociception, with less potency than morphine. Motor coordination appeared to be less involved. (C) 2000 Elsevier Science Ltd. All rights reserved.
• On the enantiomers of 2-dimethylamino-3-pentanone, key intermediates in the synthesis of analgesic alkylaminoalkylnaphthalenes
  作者：Simona Collina、Francesca Benevelli、Dina Vercesi、Victor Ghislandi

  DOI：10.1016/s0957-4166(99)00223-2

  日期：1999.6

  2-Dimethylamino-3-pentanone 1 is the key intermediate in the synthesis of alkylaminoalkylnaphthalenic analgesics. In this paper the resolution of this compound with L- and D-dibenzoyltartaric acids is described. The behavior of the diastereomeric dibenzoyltartrates and of the enantiomers in solution is investigated by NMR spectroscopy, polarimetry and chiral gas-chromatographic analysis. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis and properties of cyclic keto alkenylammonium salts
  作者：Michael E. Jung、Brian E. Love

  DOI：10.1039/c39870001288

  日期：——

  The cyclic keto alkenylammonium salts (4)–(8) have been prepared by a short, general route and their acidic and electrophilic properties examined.

  环状酮链烯基铵盐（4）–（8）是通过较短的一般路线制备的，并已对其酸性和亲电性质进行了研究。