(-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-phthalimidopropane | 245728-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-phthalimidopropane
• 英文别名: 2-[(2R)-1-(2-methyl-1,3-dioxan-2-yl)propan-2-yl]isoindole-1,3-dione
• CAS: 245728-77-2
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: BPGMCWOXIIMCLL-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-[(1r)-3-羟基-1-甲基丙基]-1H-异吲哚-1,3(2H-)-二酮 在 水 、 pyridinium chlorochromate 、 APTS 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (-)-(2R)-1-(2-methyl-1,3-dioxan-2-yl)-2-phthalimidopropane
  参考文献：
  名称：

  Stereoselective chemoenzymatic synthesis of both enantiomers of protected 4-amino-2-pentanone

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00234-7

文献信息

• 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.
• 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.