dispiro[1,3-dioxolane-2,1'-cyclohexane-4',7''-(4-methyl-1,4-diazabicyclo[3.2.1]octan-3-one)] | 211430-50-1

• 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[1,3-dioxolane-2,1'-cyclohexane-4',7''-(4-methyl-1,4-diazabicyclo[3.2.1]octan-3-one)]
• CAS: 211430-50-1
• 化学式: C₁₄H₂₂N₂O₃
• 分子量: 266.34
• InChiKey: COVCKTLBRAFRDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dispiro[1,3-dioxolane-2,1'-cyclohexane-4',7''-(4-methyl-1,4-diazabicyclo[3.2.1]octan-3-one)] 在 potassium tert-butylate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.66h， 生成
  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：

  环己酮-4-羧酸乙烯缩醛 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 lithium hydroxide 、 1,8-diazabicycloundec-7-ene 、 二苯基磷酸 、 二苯基膦叠氮化物 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 dispiro[1,3-dioxolane-2,1'-cyclohexane-4',7''-(4-methyl-1,4-diazabicyclo[3.2.1]octan-3-one)]
  参考文献：
  名称：

  Total synthesis of (±)-TAN1251A

  摘要：

  The first synthesis of novel type alkaloid (+/-)-TAN1251A possessing an antimuscarinic activity was achieved. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00797-7

文献信息

• Facile synthesis of enantiopure (−)-TAN1251A
  作者：Hirotake Mizutani、Jun Takayama、Yukio Soeda、Toshio Honda

  DOI：10.1016/s0040-4039(02)00296-4

  日期：2002.3

  Formal total synthesis of enantiopure (−)-TAN1251A, a muscarinic M1 receptor antagonist, was achieved via a spirocyclic carbonnitrogen bond formation by the use of aromatic oxidation with bis(acetoxy)iodobenzene as a key step.

  对映纯（-）-TAN1251A（毒蕈碱M 1受体拮抗剂）的正式总合成是通过使用双（乙酰氧基）碘代苯作为芳香族化合物的关键步骤，通过螺环碳氮键的形成而实现的。
• Total synthesis of (±)-TAN1251A
  作者：Shinji Nagumo、Atsushi Nishida、Chikako Yamazaki、Kikue Murashige、Norio Kawahara

  DOI：10.1016/s0040-4039(98)00797-7

  日期：1998.6

  The first synthesis of novel type alkaloid (+/-)-TAN1251A possessing an antimuscarinic activity was achieved. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Total synthesis of antimuscarinic alkaloid, (±)-TAN1251A
  作者：Shinji Nagumo、Atsushi Nishida、Chikako Yamazaki、Aoi Matoba、Kikue Murashige、Norio Kawahara

  DOI：10.1016/s0040-4020(02)00436-2

  日期：2002.6

  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.