(S)-4-[(R,E)-3,4-dideuteronona-3,8-dien-2-yl] 1-methyl 2-(tert-butoxycarbonylamino)succinate | 1410860-95-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-[(R,E)-3,4-dideuteronona-3,8-dien-2-yl] 1-methyl 2-(tert-butoxycarbonylamino)succinate
• 英文别名: 4-O-[(2R,3E)-3,4-dideuterionona-3,8-dien-2-yl] 1-O-methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
• CAS: 1410860-95-5
• 化学式: C₁₉H₃₁NO₆
• 分子量: 371.442
• InChiKey: SLPUZMYSILCZRZ-YREWJCGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-[(R,E)-3,4-dideuteronona-3,8-dien-2-yl] 1-methyl 2-(tert-butoxycarbonylamino)succinate 在 lithium hexamethyldisilazane 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以78%的产率得到(2S,3S)-2-[(S)-1-(tert-butoxycarbonylamino)-2-methoxy-2-oxoethyl]-3-deutero-3-((E)-1-deuteroprop-1-enyl)oct-7-enoic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Deuterium-Labeled (2S)-Cyclohexenyl Alanines, Biosynthetic Intermediates of Cinnabaramide

  摘要：

  Dideuterated beta-cyclohexenylalanines, proposed biosynthetic intermediates of the cinnabaramides, can be obtained from chiral alkynols via a sequence of Irland-Claisen rearrangement, ring closing metathesis, and radical decarboxylation. Feeding experiments indicate that both (2S)-beta-cyclohexenylalanines can be incorporated into cinnabaramide, while the configuration at the cyclohexenyl ring does not restrict biosynthetic processing.

  DOI：

  10.1021/ol3029548
• 作为产物：
  描述：

  (R)-non-8-en-3-yn-2-yl acetate 在 4-二甲氨基吡啶 、 lithium aluminium deuteride 、 水 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 (S)-4-[(R,E)-3,4-dideuteronona-3,8-dien-2-yl] 1-methyl 2-(tert-butoxycarbonylamino)succinate
  参考文献：
  名称：

  Stereoselective Synthesis of Deuterium-Labeled (2S)-Cyclohexenyl Alanines, Biosynthetic Intermediates of Cinnabaramide

  摘要：

  Dideuterated beta-cyclohexenylalanines, proposed biosynthetic intermediates of the cinnabaramides, can be obtained from chiral alkynols via a sequence of Irland-Claisen rearrangement, ring closing metathesis, and radical decarboxylation. Feeding experiments indicate that both (2S)-beta-cyclohexenylalanines can be incorporated into cinnabaramide, while the configuration at the cyclohexenyl ring does not restrict biosynthetic processing.

  DOI：

  10.1021/ol3029548

文献信息

• Stereoselective Synthesis of Deuterium-Labeled (2<i>S</i>)-Cyclohexenyl Alanines, Biosynthetic Intermediates of Cinnabaramide
  作者：Philipp Barbie、Liujie Huo、Rolf Müller、Uli Kazmaier

  DOI：10.1021/ol3029548

  日期：2012.12.7

  Dideuterated beta-cyclohexenylalanines, proposed biosynthetic intermediates of the cinnabaramides, can be obtained from chiral alkynols via a sequence of Irland-Claisen rearrangement, ring closing metathesis, and radical decarboxylation. Feeding experiments indicate that both (2S)-beta-cyclohexenylalanines can be incorporated into cinnabaramide, while the configuration at the cyclohexenyl ring does not restrict biosynthetic processing.