(4S,5R)-5-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 1053617-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (4S,5R)-5-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S,5R)-4-[(1,3-dioxoisoindol-2-yl)methyl]-2,2-dimethyl-5-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 1053617-02-9
• 化学式: C₂₂H₂₈N₂O₅
• 分子量: 400.475
• InChiKey: MDNKQQYBGYTNMK-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 (4S,5R)-5-Allyl-4-aminomethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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：

  (4S,5R)-5-Allyl-4-(2,2-dimethyl-propionyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 氢氧化钾 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 40.0h， 生成 (4S,5R)-5-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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

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.