(-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane | 245728-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane
• 英文别名: (-)-(R)-4-2-(2-Aminopropyl)-2-methyl-1,3-dioxane；(-)-(2R)-2-(2-aminopropyl)-2-methyl-1,3-dioxane；(2R)-1-(2-methyl-1,3-dioxan-2-yl)propan-2-amine
• CAS: 245728-69-2
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: ROZUROITAPQQCC-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane 在 W₂ Raney-nickel 、 三氟化硼乙醚 、 magnesium sulfate 、 对甲苯磺酸 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.5h， 生成 (2R,6S)-2-甲基-6-丙基哌啶
  参考文献：
  名称：

  A simple and efficient enantioselective synthesis of piperidine alkaloids dihydropinidine and isosolenopsins A, B and C

  摘要：

  A diastereospecific intramolecular Mannich-type reaction, involving enantiopure amine 4 and achiral aldehydes, is employed as the key step of an efficient total enantioselective synthesis of five piperidine alkaloids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00162-2
• 作为产物：
  描述：

  (-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-phthalimidopropane 在 一水合肼 作用下， 以 甲醇 为溶剂， 以98%的产率得到(-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane
  参考文献：
  名称：

  Improvement of the chemoenzymatic synthesis of both enantiomers of keto-protected 4-amino-2-pentanone

  摘要：

  An improved enantioselective synthesis (five steps, 37-44% yield versus seven to 10 steps, 13.5 and 12% yield, respectively) of both enantiomers of keto-protected 4-amino-2-pentanone has been realized, the key step being the microbiological reduction of 2,4-pentanedione. This study shows that microbiological reductions of the mono acetal-protected 2,4-pentanedione afforded in most cases the corresponding ketol with moderate to excellent enantiomeric excesses, depending on the microorganism used. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00167-1

文献信息

• Synthesis and Glycosidase Inhibitory Study of New Polyhydroxylated Indolizidines
  作者：Delphine Baumann、Khalil Bennis、Isabelle Ripoche、Vincent Théry、Yves Troin

  DOI：10.1002/ejoc.200800684

  日期：2008.11

  The synthesis of two polyhydroxylated indolizidines as potenticial glycosidase inhibitors is reported. The piperidine ring was formed by an intramolecular Mannich-type reaction between ethyl trans-4-oxo-2-butenoate and the two β-amino ketones (–)-1-(2-methyl-1,3-dioxan-2-yl)propan-2-amine and(+)-1-(benzyloxymethyl)-2-(2-methyl-1,3-dioxan-2-yl)ethylamine. The synthesis of this amine was performed in

  据报道，合成了两种多羟基化吲哚里西啶作为潜在的糖苷酶抑制剂。哌啶环是由 trans-4-oxo-2-butenoate 乙酯和两个 β-氨基酮 (-)-1-(2-methyl-1,3-dioxan-2-yl) 之间的分子内曼尼希型反应形成的)丙-2-胺和(+)-1-(苄氧基甲基)-2-(2-甲基-1,3-二恶烷-2-基)乙胺。该胺的合成分八步从 L-天冬氨酸进行。框架形成的关键步骤包括二羟基化、亲核取代和还原。最后一个羟基是通过水解缩醛部分然后还原得到的酮而引入的。针对多种商业糖苷酶评估了两种合成的吲哚里西啶的抑制特性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim,
• A simple synthesis of (+)- and (−)-alkaloid 241D and C-4 epimers
  作者：Stéphane Ciblat、Pierre Calinaud、Jean-Louis Canet、Yves Troin

  DOI：10.1039/a908265d

  日期：——

  An enantioselective preparation of both enantiomers of alkaloid 241D 1 and its C-4 epimer is reported. This simple and concise synthesis, seven steps from pent-3-en-2-one, involves a highly diastereoselective Mannich-type cyclisation as the key step.

  报告了生物碱 241D 1 及其 C-4 对映体两种对映体的对映选择性制备方法。这种简单明了的合成方法，以戊-3-烯-2-酮为原料，经过七个步骤，以高非对映选择性的曼尼希式环化为关键步骤。
• Stereoselective chemoenzymatic synthesis of both enantiomers of protected 4-amino-2-pentanone
  作者：Pascale Besse、Stéphane Ciblat、Jean-Louis Canet、Yves Troin、Henri Veschambre

  DOI：10.1016/s0957-4166(99)00234-7

  日期：1999.6

  An acetal protected 4-amino-2-pentanone was synthesised by two different routes in 10 and seven steps, respectively, the key step being a microbiological reduction. Both enantiomers of the amine were obtained enantiomerically pure. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Carbonnel, Sylvie; Troin, Yves, Heterocycles, 2002, vol. 57, # 10, p. 1807 - 1830
  作者：Carbonnel, Sylvie、Troin, Yves

  DOI：——

  日期：——
• A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines
  作者：Stéphane Ciblat、Pascale Besse、Jean-Louis Canet、Yves Troin、Henri Veschambre、Jacques Gelas

  DOI：10.1016/s0957-4166(99)00226-8

  日期：1999.6

  A highly diastereoselective intramolecular Mannich reaction involving enantiopure alpha-methylamine 7 and achiral aldehydes is employed to prepare enantiomerically pure 2,6-cis-disubstituted piperidines. This methodology provides an efficient and selective route to 2,6-cis-disubstituted piperidines, 2,6-cis-disubstituted 4-piperidones and 2,6-cis-disubstituted 4-piperidinols. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.