<6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-hydroxy-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate | 185515-96-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: <6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-hydroxy-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (6S,7R,8S)-9-hydroxy-6-nitro-8-prop-2-enyl-1,4-dioxaspiro[4.5]decane-7-carboxylate
• CAS: 185515-96-2
• 化学式: C₂₈H₃₉NO₇
• 分子量: 501.62
• InChiKey: PWARSWDZUKKKLQ-KTCDIBJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  108.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  <6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-hydroxy-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate 在 2,6-二甲基吡啶 、 二异丁基氢化铝 作用下， 反应 48.0h， 生成 <6S-(6α,7β,8β,9β)>-9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-methanol
  参考文献：
  名称：

  Formal synthesis of (–)-calicheamicinone and of (+)-calicheamicinone

  摘要：

  An asymmetric Diels-Alder reaction between ketene acetal 2 and the 3-nitropropenoate 10, derived from (-)-8-phenyl-menthol, affords the optically pure adduct 15, which can be converted into either enantiomer of calicheamicinone 1.

  DOI：

  10.1039/cc9960002543
• 作为产物：
  描述：

  <6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 6-nitro-9-oxo-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以100%的产率得到<6S-<6α,7β,(1S^*,2R^*,5S^*),8β>>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 9-hydroxy-6-nitro-8-(2-propenyl)-1,4-dioxaspiro<4.5>decane-7-carboxylate
  参考文献：
  名称：

  Formal synthesis of (–)-calicheamicinone and of (+)-calicheamicinone

  摘要：

  An asymmetric Diels-Alder reaction between ketene acetal 2 and the 3-nitropropenoate 10, derived from (-)-8-phenyl-menthol, affords the optically pure adduct 15, which can be converted into either enantiomer of calicheamicinone 1.

  DOI：

  10.1039/cc9960002543

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.