(2S,4S,5R)-5-Amino-2-((1E,3E,8E,10E)-pentadeca-1,3,8,10-tetraenyl)-piperidin-4-ol | 169626-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,4S,5R)-5-Amino-2-((1E,3E,8E,10E)-pentadeca-1,3,8,10-tetraenyl)-piperidin-4-ol
• 英文别名: Pseudodistomin C；(2S,4S,5R)-5-amino-2-[(1E,3E,8E,10E)-pentadeca-1,3,8,10-tetraenyl]piperidin-4-ol
• CAS: 169626-36-2
• 化学式: C₂₀H₃₄N₂O
• 分子量: 318.503
• InChiKey: OFSZNJWXVVKUPZ-MKBVZRKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-5-Amino-2-((1E,3E,8E,10E)-pentadeca-1,3,8,10-tetraenyl)-piperidin-4-ol 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.25h， 生成 Acetic acid (2S,4S,5R)-4-acetoxy-1-acetyl-5-acetylamino-piperidin-2-ylmethyl ester
  参考文献：
  名称：

  Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko

  摘要：

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.

  DOI：

  10.1021/jo00126a053
• 作为产物：
  描述：

  (3aR,6S,7aS)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(benzenesulfonylmethyl)-perhydrooxazolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester 在 盐酸 、 六甲基磷酰三胺 、 sodium amalgam 、 正丁基锂 、 N,N-二甲基-1,3-二氨基丙烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙酸乙酯 为溶剂， 反应 19.67h， 生成 (2S,4S,5R)-5-Amino-2-((1E,3E,8E,10E)-pentadeca-1,3,8,10-tetraenyl)-piperidin-4-ol
  参考文献：
  名称：

  从被膜Pseudodistoma kanoko人工合成鞘氨醇相关的哌啶生物碱拟distominmin C

  摘要：

  从d-丝氨酸合成了从冲绳被膜Pseudodistoma kanoko分离出的哌啶生物碱Pseudodistomin C（1），它为d的整个结构提供了进一步的明确证据，1在C-4和C-上具有相反的绝对构型。从假瘤菌素A（2）和B（3）的5个手性中心得自同一被膜。

  DOI：

  10.1016/0040-4020(96)00137-8

文献信息

• Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko
  作者：Jun'ichi Kobayashi、Kazushi Naitoh、Yukiko Doi、Kanako Deki、Masami Ishibashi

  DOI：10.1021/jo00126a053

  日期：1995.10

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.
• Total synthesis of pseudodistomin C, a sphingosine-related piperidine alkaloid from tunicate Pseudodistoma kanoko
  作者：Yukiko Doi、Masami Ishibashi、Jun'ichi Kobayashi

  DOI：10.1016/0040-4020(96)00137-8

  日期：1996.3

  Pseudodistomin C (1), a piperidine alkaloid isolated from the Okinawan tunicate Pseudodistoma kanoko, has been synthesized from d-serine to provide a further unambiguous evidence for the whole structure of 1 which possessed the opposite absolute configurations at the C-4 and C-5 chiral centers from those of pseudodistomins A (2) and B (3) obtained from the same tunicate.

  从d-丝氨酸合成了从冲绳被膜Pseudodistoma kanoko分离出的哌啶生物碱Pseudodistomin C（1），它为d的整个结构提供了进一步的明确证据，1在C-4和C-上具有相反的绝对构型。从假瘤菌素A（2）和B（3）的5个手性中心得自同一被膜。