(+)-(2S)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane | 245728-79-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2S)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane
• 英文别名: (+)-(2S)-2-(2-aminopropyl)-2-methyl-1,3-dioxane；(S)-(+)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane；(+)-(S)-2-(2-Aminopropyl)-2-methyl-1,3-dioxane；(2S)-1-(2-methyl-1,3-dioxan-2-yl)propan-2-amine
• CAS: 245728-79-4
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: ROZUROITAPQQCC-ZETCQYMHSA-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：

  (+)-(2S)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane 在 magnesium sulfate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (-)-(2S,6S)-1-aza-6-methyl-2-phenyl-1',3'-dioxaspiro<5.5>undecane
  参考文献：
  名称：

  A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00226-8
• 作为产物：
  描述：

  (SS,S)-(+)-N-(p-toluensulfinyl)-4-aminopentan-2-one 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 12.5h， 生成 (+)-(2S)-1-(2-methyl-1,3-dioxan-2-yl)-2-aminopropane
  参考文献：
  名称：

  由亚磺胺（N-亚磺酰亚胺）直接不对称合成β-氨基酮。（-）-吲哚唑烷209B的合成。

  摘要：

  直接从甲基酮的烯醇钾和对映体纯的亚氨磺酸亚胺制得的N-亚磺酰基β-氨基酮在一个罐中转化为受保护的氨基酮，这是组装哌啶的重要手性结构单元。该方法的实用性在（-）-吲哚唑烷209B的简明不对称合成中得到了说明。[反应：看文字]

  DOI：

  10.1021/ol035981+

文献信息

• 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.
• Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity
  作者：Haruhisa Kikuchi、Kazunori Sasaki、Jun'ichi Sekiya、Yasuo Maeda、Aiko Amagai、Yuzuru Kubohara、Yoshiteru Oshima

  DOI：10.1016/j.bmc.2004.04.001

  日期：2004.6

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.
• A simple and efficient enantioselective synthesis of piperidine alkaloids dihydropinidine and isosolenopsins A, B and C
  作者：Stéphane Ciblat、Pascale Besse、Vassiliki Papastergiou、Henri Veschambre、Jean-Louis Canet、Yves Troin

  DOI：10.1016/s0957-4166(00)00162-2

  日期：2000.6

  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.
• Improvement of the chemoenzymatic synthesis of both enantiomers of keto-protected 4-amino-2-pentanone
  作者：Pascale Besse、Stéphane Ciblat、Jean-Louis Canet、Yves Troin、Henri Veschambre

  DOI：10.1016/s0957-4166(00)00167-1

  日期：2000.6

  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.