(2R)-2-[(1S,4S)-2-bromo-4-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxycyclohex-2-en-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid | 339266-17-0

• 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: (2R)-2-[(1S,4S)-2-bromo-4-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxycyclohex-2-en-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
• CAS: 339266-17-0
• 化学式: C₂₁H₃₈BrNO₅Si
• 分子量: 492.526
• InChiKey: WSPSSXCGBUHEGT-ZMSDIMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1S-顺式)-3-溴-3,5-环己二烯-1,2-二醇 在 咪唑 、 4-二甲氨基吡啶 、 potassium diazodicarboxylate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 、 (2R)-2-[(1S,4S)-2-bromo-4-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxycyclohex-2-en-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
  参考文献：
  名称：

  Total Synthesis of Dihydrocodeine and Hydrocodone via a Double Claisen Rearrangement and C-10/C-11 Closure Strategy

  摘要：

  Dihydrocodeine and hydrocodone were synthesized from bromobenzene in 16 and 17 transformations, respectively. The key steps involved the toluene dioxygenase-mediated dihydroxylation of bromobenzene by whole-cell fermentation with E. coli JM109(pDTG601A), Kazmaier-Claisen rearrangement of glycinate ester, Claisen rearrangement to set the C-13 quaternary center, and C-10-C-11 closure. Experimental procedures are provided for the key steps.

  DOI：

  10.1055/s-0032-1318114

文献信息

• Total Synthesis of Dihydrocodeine and Hydrocodone via a Double Claisen Rearrangement and C-10/C-11 Closure Strategy
  作者：Tomas Hudlicky、Vimal Varghese

  DOI：10.1055/s-0032-1318114

  日期：——

  Dihydrocodeine and hydrocodone were synthesized from bromobenzene in 16 and 17 transformations, respectively. The key steps involved the toluene dioxygenase-mediated dihydroxylation of bromobenzene by whole-cell fermentation with E. coli JM109(pDTG601A), Kazmaier-Claisen rearrangement of glycinate ester, Claisen rearrangement to set the C-13 quaternary center, and C-10-C-11 closure. Experimental procedures are provided for the key steps.