dispiro[1-tert-butoxycarbonyl-3-hydroxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane] | 460355-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: dispiro[1-tert-butoxycarbonyl-3-hydroxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]
• 英文别名: Tert-butyl 2-hydroxy-9,12-dioxa-4-azadispiro[4.2.48.25]tetradecane-4-carboxylate
• CAS: 460355-83-3
• 化学式: C₁₆H₂₇NO₅
• 分子量: 313.394
• InChiKey: URTWTZKGTTZVGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dispiro[1-tert-butoxycarbonyl-3-hydroxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane] 在 三氟乙酸 作用下， 反应 0.5h， 生成 1,4-Dioxa-9-aza-dispiro[4.2.4.2]tetradecan-11-ol
  参考文献：
  名称：

  Total synthesis of antimuscarinic alkaloid, (±)-TAN1251A

  摘要：

  The total synthesis of (+/-)-TAN1251A possessing an antimuscarinic activity was achieved. Carboxylic acid (1) was converted into carbamate (3) through a sequence of alkylation and Curtius rearrangement. After a few functional group interconversions of 3, the corresponding amine (9) was converted into an azaspiro molecule (18) through cyclization and installation of a C-2 unit. Hydrolysis of 18 followed by lactam formation afforded tricyclic compound (20). Coupling of 20 with aldehyde (22) gave two epimeric adducts, (23A) and (23B), which were converted into TAN1251A by four steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00436-2
• 作为产物：
  描述：

  11-(tert-Butyl-dimethyl-silanyloxy)-1,4-dioxa-9-aza-dispiro[4.2.4.2]tetradecane-9-carboxylic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以1.07 g的产率得到dispiro[1-tert-butoxycarbonyl-3-hydroxypyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]
  参考文献：
  名称：

  Total synthesis of antimuscarinic alkaloid, (±)-TAN1251A

  摘要：

  The total synthesis of (+/-)-TAN1251A possessing an antimuscarinic activity was achieved. Carboxylic acid (1) was converted into carbamate (3) through a sequence of alkylation and Curtius rearrangement. After a few functional group interconversions of 3, the corresponding amine (9) was converted into an azaspiro molecule (18) through cyclization and installation of a C-2 unit. Hydrolysis of 18 followed by lactam formation afforded tricyclic compound (20). Coupling of 20 with aldehyde (22) gave two epimeric adducts, (23A) and (23B), which were converted into TAN1251A by four steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00436-2