N,N-dimethyl-1-adamantylacetamide | 31897-94-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-dimethyl-1-adamantylacetamide
• 英文别名: 2-(adamantan-1-yl)-N,N-dimethylacetamide；N,N-Dimethyladamantan-1-acetamid；2-(1-adamantyl)-N,N-dimethylacetamide
• CAS: 31897-94-6
• 化学式: C₁₄H₂₃NO
• 分子量: 221.343
• InChiKey: NIBRCFLQLASDFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.928
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-1-adamantylacetamide 在 lithium aluminium tetrahydride 、 双氧水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 47.0h， 生成 1-(1-金刚烷基)乙烯
  参考文献：
  名称：

  Preparation of homochiral crown ether containing (S)-1-(1-adamantyl)ethane-1,2-diol as a chiral subunit and its enantioselective complexation with an organic ammonium cation

  摘要：

  Homochiral 1-(1-adamantyl)ethane-1,2-diol(5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and H-1 n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the H-1 n.m.r. spectroscopic method.

  DOI：

  10.1016/0957-4166(94)80125-8
• 作为产物：
  描述：

  1-金刚烷乙酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 32.0h， 生成 N,N-dimethyl-1-adamantylacetamide
  参考文献：
  名称：

  Preparation of homochiral crown ether containing (S)-1-(1-adamantyl)ethane-1,2-diol as a chiral subunit and its enantioselective complexation with an organic ammonium cation

  摘要：

  Homochiral 1-(1-adamantyl)ethane-1,2-diol(5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and H-1 n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the H-1 n.m.r. spectroscopic method.

  DOI：

  10.1016/0957-4166(94)80125-8

文献信息

• Chemical transformations of tetracyclo[3.3.1.13,7.01,3]decane (1,3-dehydroadamantane): II. Reaction of 1,3-dehydroadamantane with N,N-dialkylcarboxamides
  作者：V. M. Mokhov、G. M. Butov、K. R. Saad

  DOI：10.1134/s107042801701002x

  日期：2017.1

  Alkylation of N,N-dialkylcarboxamides with 1,3-dehydroadamantane has been accomplished for the first time. The reaction involves the C-H bond in the alpha-position with respect to the carbonyl group and provides a convenient one- step preparation of substituted carboxylic acid amides containing an 1-adamantyl substituent and a pharmacophoric group in the amide moiety.
• Chemistry of adamantane. VII. Adamantanealkanamines as potential antidepressant and anti-Parkinson agents
  作者：Jiban K. Chakrabarti、Michael J. Foulis、Terrence M. Hotten、Stephen S. Szinai、Alec Todd

  DOI：10.1021/jm00252a007

  日期：1974.6
• Preparation of homochiral crown ether containing (S)-1-(1-adamantyl)ethane-1,2-diol as a chiral subunit and its enantioselective complexation with an organic ammonium cation
  作者：Koichiro Naemura、Takashi Mizo-oku、Kimiko Kamada、Keiji Hirose、Yoshito Tobe、Masami Sawada、Yoshio Takai

  DOI：10.1016/0957-4166(94)80125-8

  日期：1994.8

  Homochiral 1-(1-adamantyl)ethane-1,2-diol(5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and H-1 n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the H-1 n.m.r. spectroscopic method.