(2S,3R)-3-dimethylamino-3-phenylpropane-1,2-diol | 1396162-78-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3R)-3-dimethylamino-3-phenylpropane-1,2-diol
• 英文别名: (2S,3R)-3-(dimethylamino)-3-phenylpropane-1,2-diol
• CAS: 1396162-78-9
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: PUACZVHNINBNAU-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-肉桂醇 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 titanium(IV)isopropoxide 、 D-(-)-酒石酸二异丙酯 、 N,N-二异丙基乙胺 、 potassium hydroxide 、 zinc dibromide 作用下， 以 二氯甲烷 、 水 、 氯苯 为溶剂， 反应 113.2h， 生成 (2S,3R)-3-dimethylamino-3-phenylpropane-1,2-diol
  参考文献：
  名称：

  Determination of the Stereochemistry of C-2’ and C-3’ Positions of Taxine NA-1 (2’-Hydroxytaxine II) by the Asymmetric Synthesis of the Reductive Degradation Product of Its Side Chain Moiety

  摘要：

  The reductive degradation of taxine NA-1 (2'-hydroxytaxine II) with n-Bu4NBH4 gave taxinine A and (-)-3-dimethylarnino-3-phenylpropane-1,2-diol (1) in addition to 11,12-dihydrotaxinine A. The relative stereochemistry of (-)-1 was identical with syn-3-dimethylamino-3-phenylpropane-1,2-diol, (+/-)-1b, which was synthesized from cis-2,3-epoxy-3-phenylpropan-1-ol, (+/-)-7. The absolute configuration of (-)-1 was certified by comparison of the specific optical rotation and the spectroscopic data of (-)-1 with those of (+)-1b and (-)-1b, which were enantioselectively synthesized by Sharp less asymmetric epoxidation reaction of cis-cinnamyl alcohol (6), respectively. As the result, the relative and absolute configuration of (-)-1 was same with that of (-)-1b possessing (2R, 35) configuration. Thus, the absolute configuration of the side chain of taxine NA-1 (2'-hydroxytaxine II) at C-2' and C-3' positions was determined to be (2'R, 3'S).

  DOI：

  10.3987/com-12-12480

文献信息

• Determination of the Stereochemistry of C-2’ and C-3’ Positions of Taxine NA-1 (2’-Hydroxytaxine II) by the Asymmetric Synthesis of the Reductive Degradation Product of Its Side Chain Moiety
  作者：Wanxia Tang、Masayoshi Ando、Hiroshi Minato、Mariko Ando

  DOI：10.3987/com-12-12480

  日期：——

  The reductive degradation of taxine NA-1 (2'-hydroxytaxine II) with n-Bu4NBH4 gave taxinine A and (-)-3-dimethylarnino-3-phenylpropane-1,2-diol (1) in addition to 11,12-dihydrotaxinine A. The relative stereochemistry of (-)-1 was identical with syn-3-dimethylamino-3-phenylpropane-1,2-diol, (+/-)-1b, which was synthesized from cis-2,3-epoxy-3-phenylpropan-1-ol, (+/-)-7. The absolute configuration of (-)-1 was certified by comparison of the specific optical rotation and the spectroscopic data of (-)-1 with those of (+)-1b and (-)-1b, which were enantioselectively synthesized by Sharp less asymmetric epoxidation reaction of cis-cinnamyl alcohol (6), respectively. As the result, the relative and absolute configuration of (-)-1 was same with that of (-)-1b possessing (2R, 35) configuration. Thus, the absolute configuration of the side chain of taxine NA-1 (2'-hydroxytaxine II) at C-2' and C-3' positions was determined to be (2'R, 3'S).