Tert-butyl 2'-oxospiro[1,3-dioxolane-2,3'-indole]-1'-carboxylate | 365222-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Tert-butyl 2'-oxospiro[1,3-dioxolane-2,3'-indole]-1'-carboxylate
• CAS: 365222-72-6
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: HNKIHBMDQSUFTL-UHFFFAOYSA-N

物化性质

• 沸点：
  403.0±55.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2'-oxospiro[1,3-dioxolane-2,3'-indole]-1'-carboxylate 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-[2-(Allyl-tert-butoxycarbonyl-amino)-phenyl]-[1,3]dioxolane-2-carboxylic acid
  参考文献：
  名称：

  叠氮基叠氮烷的对映选择性合成和关键中间体的选择性官能化。

  摘要：

  已经实现了对映体选择性合成米托烷核（-）-1。关键步骤包括采用闭环复分解快速组装关键的八元环中间体。然后通过使用基于肽的不对称酰基转移催化剂（从候选催化剂的平行筛选中发现）来实现高级仲醇的动力学拆分。然后将光学纯的材料转化为三聚氰胺核，这是选择性修饰的进一步研究的主题，以生产几种含有三聚硅氧烷环系统的取代化合物。

  DOI：

  10.1021/jo0269013
• 作为产物：
  描述：

  靛红 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 Tert-butyl 2'-oxospiro[1,3-dioxolane-2,3'-indole]-1'-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of a Mitosane Core Assisted by Diversity-Based Catalyst Discovery

  摘要：

  [GRAPHICS]Synthesis of mitosane 1 in optically pure form is reported. A retrosynthetic plan that proceeds through racemic allylic alcohol 3 was carried out. This intermediate served as a test substrate for a rapid screen of a small library (152 members) of peptide-based kinetic resolution catalysts. Peptide 9 was found to effect kinetic resolution with k(rel) = 27.Alcohol (-)-3 was then converted to optically pure (-)-1 in eight steps.

  DOI：

  10.1021/ol016372+

文献信息

• Stereoselective Synthesis of a 4a,9-Disubstituted Octahydroacridine from Isatin
  作者：Tadashi Katoh、Hideki Abe、Sakae Aoyagi、Yoshimi Sato、Kazuhiro Watanabe、Chihiro Kibayashi

  DOI：10.3987/com-08-s(f)57

  日期：——

  An efficient method for stereoselective synthesis of a 4a,9-disubstituted octahydroacridine derivative from isatin (2,3-indolinedione) was developed; the method is based on an intramolecular reaction of an N-acyliminium ion with a conjugated diene system.
• Enantioselective Synthesis of an Aziridinomitosane and Selective Functionalizations of a Key Intermediate
  作者：Nikolaos Papaioannou、Jarred T. Blank、Scott J. Miller

  DOI：10.1021/jo0269013

  日期：2003.4.1

  An enantioselective synthesis of mitosane core (-)-1 has been achieved. Key steps include a rapid assembly of a key eight-membered-ring intermediate employing ring-closing metathesis. Kinetic resolution of an advanced secondary alcohol was then accomplished by using a peptide-based asymmetric acyl transfer catalyst that was discovered from a parallel screen of catalyst candidates. Optically pure material

  已经实现了对映体选择性合成米托烷核（-）-1。关键步骤包括采用闭环复分解快速组装关键的八元环中间体。然后通过使用基于肽的不对称酰基转移催化剂（从候选催化剂的平行筛选中发现）来实现高级仲醇的动力学拆分。然后将光学纯的材料转化为三聚氰胺核，这是选择性修饰的进一步研究的主题，以生产几种含有三聚硅氧烷环系统的取代化合物。
• Enantioselective Synthesis of a Mitosane Core Assisted by Diversity-Based Catalyst Discovery
  作者：Nikolaos Papaioannou、Catherine A. Evans、Jarred T. Blank、Scott J. Miller

  DOI：10.1021/ol016372+

  日期：2001.9.1

  [GRAPHICS]Synthesis of mitosane 1 in optically pure form is reported. A retrosynthetic plan that proceeds through racemic allylic alcohol 3 was carried out. This intermediate served as a test substrate for a rapid screen of a small library (152 members) of peptide-based kinetic resolution catalysts. Peptide 9 was found to effect kinetic resolution with k(rel) = 27.Alcohol (-)-3 was then converted to optically pure (-)-1 in eight steps.