<3R-(3α,4aβ,8β,8aβ)>-hexahydro-5-oxo-8-<<(2-propenyloxy)carbonyl>amino>spiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-3-yl 2,2-dimethylpropanoate | 225368-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: <3R-(3α,4aβ,8β,8aβ)>-hexahydro-5-oxo-8-<<(2-propenyloxy)carbonyl>amino>spiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-3-yl 2,2-dimethylpropanoate
• 英文别名: [(3'R,4'aS,8'S,8'aR)-5'-oxo-8'-(prop-2-enoxycarbonylamino)spiro[1,3-dioxolane-2,7'-3,4,4a,6,8,8a-hexahydro-1H-isochromene]-3'-yl] 2,2-dimethylpropanoate
• CAS: 225368-08-1
• 化学式: C₂₀H₂₉NO₈
• 分子量: 411.452
• InChiKey: WYJLBJXUFBLWRB-XNISGKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  <3R-(3α,4aβ,8β,8aβ)>-hexahydro-5-oxo-8-<<(2-propenyloxy)carbonyl>amino>spiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-3-yl 2,2-dimethylpropanoate 在 吡啶 、 2,6-二甲基吡啶 、 chromium(VI) oxide 、 四(三苯基膦)钯 、 cerium(III) chloride 、 次氯酸叔丁酯 、 苯基溴化硒 、 二甲基二环氧乙烷 、 二异丁基氢化铝 、 5,5-二甲基-1,3-环己二酮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl 5R-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5,6-dihydro-3-oxo-5-<(trimethylsilyl)ethynyl>spiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-8-yl>carbamate
  参考文献：
  名称：

  Synthesis and X-ray crystal structure of (?)-calicheamicinone

  摘要：

  Diels-Alder reaction between ketene acetal 3 and the beta-nitroacrylate ester 12 of (-)-8-phenylmenthol gave optically pure ketone 17. This substance was modified in such a way as to remove the chiral auxiliary and afford the epimeric silyl ethers 20M and 20m. Following procedures worked out using racemic materials, both 20M and 20m were converted into optically pure (-)-calicheamicinone (1). This is a crystalline substance, and an X-ray structure determination was carried out. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4020(98)01140-5
• 作为产物：
  描述：

  <3R-(3α,4aβ,5α,8β,8aβ)>-8-amino-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>hexahydrospiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-3-yl 2,2-dimethylpropanoate 在 吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 <3R-(3α,4aβ,8β,8aβ)>-hexahydro-5-oxo-8-<<(2-propenyloxy)carbonyl>amino>spiro<1H-2-benzopyran-7(3H),2'-<1,3>dioxolan>-3-yl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis and X-ray crystal structure of (?)-calicheamicinone

  摘要：

  Diels-Alder reaction between ketene acetal 3 and the beta-nitroacrylate ester 12 of (-)-8-phenylmenthol gave optically pure ketone 17. This substance was modified in such a way as to remove the chiral auxiliary and afford the epimeric silyl ethers 20M and 20m. Following procedures worked out using racemic materials, both 20M and 20m were converted into optically pure (-)-calicheamicinone (1). This is a crystalline substance, and an X-ray structure determination was carried out. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4020(98)01140-5

文献信息

• Synthesis and X-ray crystal structure of (?)-calicheamicinone
  作者：Derrick L.J. Clive、Yunxin Bo、Natesan Selvakumar、Robert McDonald、Bernard D. Santarsiero

  DOI：10.1016/s0040-4020(98)01140-5

  日期：1999.3

  Diels-Alder reaction between ketene acetal 3 and the beta-nitroacrylate ester 12 of (-)-8-phenylmenthol gave optically pure ketone 17. This substance was modified in such a way as to remove the chiral auxiliary and afford the epimeric silyl ethers 20M and 20m. Following procedures worked out using racemic materials, both 20M and 20m were converted into optically pure (-)-calicheamicinone (1). This is a crystalline substance, and an X-ray structure determination was carried out. (C) 1999 Elsevier Science Ltd. Ail rights reserved.