sedamine | 7773-46-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: sedamine
• 英文别名: rac. Sedamin；DL-Sedamin；Allosedamine；2-(1-methylpiperidin-2-yl)-1-phenylethanol
• CAS: 7773-46-8
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: GOWRYACIDZSIHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-methoxy-piperidine-1-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 四氯化钛 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 sedamine
  参考文献：
  名称：

  Electroorganic chemistry. 46. A new carbon-carbon bond forming reaction at the .alpha.-position of amines utilizing anodic oxidation as a key step

  摘要：

  DOI：

  10.1021/ja00395a029

文献信息

• The use of nitrones in the synthesis of anatoxin-a, very fast death factor
  作者：Joseph J. Tufariello、Harold Meckler、K.Pushpananda A. Senaratne

  DOI：10.1016/s0040-4020(01)96699-2

  日期：1985.1

  The synthesis of anatoxin-a (1) was completed by using the cycloaddition of 1-pyrroline 1-oxide (2) onto dienol (6), a reaction which proceeded with high stereoselectivity, regioselectivity, and site selectivity. The resultant adduct (i.e. 7) was oxidized to a second nitrone (i.e. 8) which undergoes a second closure to afford cycloadduct 9a with regiospecificity. The conversion of 9a into anatoxin-a

  Anatoxin-a（1）的合成是通过将1-pyrroline 1-oxide（2）环加成到二烯醇（6）上来完成的，该反应以高立体选择性，区域选择性和位点选择性进行。将所得的加合物（即7）氧化为第二硝酮（即8），将其进行第二次封闭以提供具有区域特异性的环加合物9a。将9a转化为盐酸Anatoxin-a（1 ·HCl）既直接又有效。
• Synthesis of a 3,4-Dihydro-1,3-oxazin-2-ones Skeleton via an Intermolecular [4 + 2] Process of <i>N</i>-Acyliminium Ions with Ynamides/Terminal Alkynes
  作者：Xiao-Li Han、Xiao-Di Nie、Zhao-Dan Chen、Chang-Mei Si、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1021/acs.joc.0c01692

  日期：2020.11.6

  An approach to access functionalized 3,4-dihydro-1,3-oxazin-2-ones has been developed by reacting semicyclic N,O-acetals 5 and 6 with ynamides 7 or terminal alkynes 8 in a one-pot fashion. The reaction went through a formal [4 + 2] cycloaddition process to generate a number of functionalized 3,4-dihydro-1,3-oxazin-2-ones 9a-9ak and 10a-10bc in yields of 34-97%. In addition, the utility of this transformation was demonstrated by the synthesis of (±)-sedamine 13.
• Alkaloids of some european and macaronesian sedoideae and sempervivoideae (Crassulaceae)
  作者：Jan F. Stevens、Henk 'T Hart、Henk Hendriks、Theo M. Malingré

  DOI：10.1016/s0031-9422(00)97554-x

  日期：1992.1

  Some 22 pyrrolidine and piperdine alkaloids were detected in the leafy parts of Sedum acre, S. aetnense, S. anglicum, S. brissemoreti, S. farinosum, S. fusiforme, S. lancerottense, S. melanantherum, and S. nudum. In addition to the alkaloids known from S. acre, 1-(2-pyrrolidyl)-propan-2-one and 2-monosubstituted piperidine alkaloids bearing butan-2-one, butan-2-ol, pentan-2-one and pentan-2-ol sidechains were identified. Phenylethylamine was isolated from the vegetative parts of S. album. In S. lydium, S. meyeri-johannis, and 16 species of S. series Rupestria, Aeonium, Greenovia, Jovibarba and Sempervivum no alkaloids could be detected. The results indicate a correlation between the presence of alkaloids and the major evolutionary trends in the European and Macaronesian Crassulaceae.
• DRIESSENS, FRANK;HOOTELE, CLAUDE, CAN. J. CHEM., 69,(1991) N, C. 211-217
  作者：DRIESSENS, FRANK、HOOTELE, CLAUDE

  DOI：——

  日期：——
• Electroorganic chemistry. 46. A new carbon-carbon bond forming reaction at the .alpha.-position of amines utilizing anodic oxidation as a key step
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenji Tsubata

  DOI：10.1021/ja00395a029

  日期：1981.3