(3aR,7aR)-N-[(R)-(4-bromophenyl)-(1,3-dithian-2-yl)methyl]-2-oxo-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-amine | 1281868-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,7aR)-N-[(R)-(4-bromophenyl)-(1,3-dithian-2-yl)methyl]-2-oxo-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-amine
• CAS: 1281868-07-2
• 化学式: C₂₃H₃₇BrN₃OPS₂
• 分子量: 546.576
• InChiKey: CLUCHMHEMANYMN-YPAWHYETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-二噻烷 、 (3aR,7aR)-2-((4-bromobenzylidene)amino)-1,3-diisopropyloctahydrobenzo[d][1,3,2]diazaphosphole 2-oxide 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以77%的产率得到(3aR,7aR)-N-[(R)-(4-bromophenyl)-(1,3-dithian-2-yl)methyl]-2-oxo-1,3-di(propan-2-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-amine
  参考文献：
  名称：

  Asymmetric Synthesis of α-Amino-1,3-dithianes via Chiral N-Phosphonyl Imine-Based Umpolung Reaction Without Using Chromatography and Recrystallization

  摘要：

  A series of alpha-amino-1,3-dithianes have been synthesized via the asymmetric Umpolung reaction of 2-lithio-1,3-dithianes with chiral N-phosphonyl imines in good chemical yields (up to 82%) and good to excellent diastereoselectivities (>99:1). The manner by which chiral N-phosphonyl imines are slowly added into the solution of 2-lithio-1,3-dithiane was found to be crucial for achieving excellent diastereoselectivity. The current synthesis was proven to follow the GAP chemistry (group-assistant-purification chemistry) process, which avoids traditional purification techniques of chromatography or recrystallization, i.e., the pure chiral alpha-amino-1,3-dithianes attached with the chiral N-phosphonyl group were readily obtained by washing the solid crude products with hexane or a mixture of hexane ethyl acetate.

  DOI：

  10.1021/jo200070d

文献信息

• Asymmetric Synthesis of α-Amino-1,3-dithianes via Chiral <i>N</i>-Phosphonyl Imine-Based Umpolung Reaction Without Using Chromatography and Recrystallization
  作者：Padmanabha V. Kattamuri、Teng Ai、Suresh Pindi、Yinwei Sun、Peng Gu、Min Shi、Guigen Li

  DOI：10.1021/jo200070d

  日期：2011.4.15

  A series of alpha-amino-1,3-dithianes have been synthesized via the asymmetric Umpolung reaction of 2-lithio-1,3-dithianes with chiral N-phosphonyl imines in good chemical yields (up to 82%) and good to excellent diastereoselectivities (>99:1). The manner by which chiral N-phosphonyl imines are slowly added into the solution of 2-lithio-1,3-dithiane was found to be crucial for achieving excellent diastereoselectivity. The current synthesis was proven to follow the GAP chemistry (group-assistant-purification chemistry) process, which avoids traditional purification techniques of chromatography or recrystallization, i.e., the pure chiral alpha-amino-1,3-dithianes attached with the chiral N-phosphonyl group were readily obtained by washing the solid crude products with hexane or a mixture of hexane ethyl acetate.