tert-butyl (3aR,8bS)-6,7-dimethoxy-2,3,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrole-3a-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: tert-butyl (3aR,8bS)-6,7-dimethoxy-2,3,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrole-3a-carboxylate
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: HBVGFYFBTQEICU-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aR,8bS)-6,7-dimethoxy-2,3,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrole-3a-carboxylate 、 三氟乙酸 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Direct chromatographic enantioresolution of fully constrained β-amino acids: exploring the use of high-molecular weight chiral selectors

  摘要：

  To the best of our knowledge enantioselective chromatographic protocols on beta-amino acids with polysaccharide-based chiral stationary phases (CSPs) have not yet appeared in the literature. Therefore, the primary objective of this work was the development of chromatographic methods based on the use of an amylose derivative CSP (Lux Amylose-2), enabling the direct normal-phase (NP) enantioresolution of four fully constrained beta-amino acids. Also, the results obtained with the glycopeptide-type Chirobiotic T column employed in the usual polar-ionic (PI) mode of elution are compared with those achieved with the polysaccharide-based phase. The Lux Amylose-2 column, in combination with alkyl sulfonic acid containing NP eluent systems, prevailed over the Chirobiotic T one, when used under the PI mode of elution, and hence can be considered as the elective choice for the enantioseparation of this class of rigid beta-amino acids. Moreover, the extraordinarily high alpha (up to 4.60) and R (S) (up to 10.60) values provided by the polysaccharidic polymer, especially when used with camphor sulfonic acid containing eluent systems, make it also suitable for preparative-scale enantioisolations.

  DOI：

  10.1007/s00726-014-1683-5
• 作为产物：
  描述：

  5,6-二甲氧基茚酮 在 sodium tetrahydroborate 、 sodium azide 、 sodium hydride 、 三苯基膦 、 4-((S)-(phenanthren-9-yloxy)((2R,4S,8R)-8-vinylquinuclidin-2-yl)methyl)quinolin-6-ol 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 tert-butyl (3aR,8bS)-6,7-dimethoxy-2,3,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrole-3a-carboxylate
  参考文献：
  名称：

  茚满酮羧酸盐对乙烯基硒酮的有机催化迈克尔加成反应，用于多环吡咯烷的不对称合成

  摘要：

  C6'羟基金鸡纳衍生物催化的外消旋茚满酮羧酸酯与乙烯基硒酮的迈克尔加成反应是合成序列的关键步骤，可实际获得高度对映体富集（高达ee达98％ee）的具有连续的叔和季立体中心的多环吡咯烷。

  DOI：

  10.1016/j.tet.2012.08.077

文献信息

• Organocatalytic Michael addition of indanone carboxylates to vinyl selenone for the asymmetric synthesis of polycyclic pyrrolidines
  作者：Silvia Sternativo、Ola Walczak、Benedetta Battistelli、Lorenzo Testaferri、Francesca Marini

  DOI：10.1016/j.tet.2012.08.077

  日期：2012.12

  racemic indanone carboxylates to vinyl selenone catalyzed by C6′hydroxyl cinchona derivatives is the key step of a synthetic sequence for a practical access to highly enantioenriched (up to 98% ee) polycyclic pyrrolidines bearing contiguous tertiary and quaternary stereocenters.

  C6'羟基金鸡纳衍生物催化的外消旋茚满酮羧酸酯与乙烯基硒酮的迈克尔加成反应是合成序列的关键步骤，可实际获得高度对映体富集（高达ee达98％ee）的具有连续的叔和季立体中心的多环吡咯烷。
• Direct chromatographic enantioresolution of fully constrained β-amino acids: exploring the use of high-molecular weight chiral selectors
  作者：Roccaldo Sardella、Federica Ianni、Antonella Lisanti、Stefania Scorzoni、Francesca Marini、Silvia Sternativo、Benedetto Natalini

  DOI：10.1007/s00726-014-1683-5

  日期：2014.5

  To the best of our knowledge enantioselective chromatographic protocols on beta-amino acids with polysaccharide-based chiral stationary phases (CSPs) have not yet appeared in the literature. Therefore, the primary objective of this work was the development of chromatographic methods based on the use of an amylose derivative CSP (Lux Amylose-2), enabling the direct normal-phase (NP) enantioresolution of four fully constrained beta-amino acids. Also, the results obtained with the glycopeptide-type Chirobiotic T column employed in the usual polar-ionic (PI) mode of elution are compared with those achieved with the polysaccharide-based phase. The Lux Amylose-2 column, in combination with alkyl sulfonic acid containing NP eluent systems, prevailed over the Chirobiotic T one, when used under the PI mode of elution, and hence can be considered as the elective choice for the enantioseparation of this class of rigid beta-amino acids. Moreover, the extraordinarily high alpha (up to 4.60) and R (S) (up to 10.60) values provided by the polysaccharidic polymer, especially when used with camphor sulfonic acid containing eluent systems, make it also suitable for preparative-scale enantioisolations.