(4R,6R)-dihydroxy-4-(10(Z)-heptadecenyl)-2-cyclohexenone | 903522-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,6R)-dihydroxy-4-(10(Z)-heptadecenyl)-2-cyclohexenone
• 英文别名: (4R,6S)-4-[(Z)-heptadec-10-enyl]-4,6-dihydroxycyclohex-2-en-1-one
• CAS: 903522-36-1
• 化学式: C₂₃H₄₀O₃
• 分子量: 364.569
• InChiKey: QGMORWLDWJPVQC-CHXUTICSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯苯甲酰氯 、 (4R,6R)-dihydroxy-4-(10(Z)-heptadecenyl)-2-cyclohexenone 反应 0.5h， 以6.0 mg的产率得到4-Chloro-benzoic acid (1S,5R)-5-((Z)-heptadec-10-enyl)-5-hydroxy-2-oxo-cyclohex-3-enyl ester
  参考文献：
  名称：

  Two New Cytotoxic Compounds from Tapirira guianensis

  摘要：

  Two new cytotoxic compounds, 2-[10(Z)-heptadecenyl]-1,4-hydroquinone (1) and (4R,6R)-dihydroxy-4-[10(Z)-heptadecenyl]-[10(Z)heptadecenyl]-2-cyclohexenone (2) have been isolated from a MeOH extract of seeds of Tapirira guianensis. The structures were established through spectral analysis of the isolates and their derivatives.

  DOI：

  10.1021/np970422v
• 作为产物：
  描述：

  (3S,4aR,7S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-8a-((Z)-heptadec-10-enyl)-3-methyl-tetrahydro-benzo[1,4]dioxine-2,6-dione 在 吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 (4R,6R)-dihydroxy-4-(10(Z)-heptadecenyl)-2-cyclohexenone
  参考文献：
  名称：

  General Synthesis for Chiral 4-Alkyl-4-hydroxycyclohexenones

  摘要：

  Some selective transformations of resorcinol-derived cyclohexadienone are reported. Efforts led to a structure reported to display anticancer properties. On the basis of the results, the structures for natural products reported to contain a 4,6-dihydroxy-4-alkyl-cyclohexenone nucleus are corrected.

  DOI：

  10.1021/ol061000s

文献信息

• General Synthesis for Chiral 4-Alkyl-4-hydroxycyclohexenones
  作者：Christophe Hoarau、Thomas R. R. Pettus

  DOI：10.1021/ol061000s

  日期：2006.6.1

  Some selective transformations of resorcinol-derived cyclohexadienone are reported. Efforts led to a structure reported to display anticancer properties. On the basis of the results, the structures for natural products reported to contain a 4,6-dihydroxy-4-alkyl-cyclohexenone nucleus are corrected.
• Two New Cytotoxic Compounds from <i>Tapirira guianensis</i>
  作者：Jorge M. David、Juceni P. Chávez、Hee-Byung Chai、John M. Pezzuto、Geoffrey A. Cordell

  DOI：10.1021/np970422v

  日期：1998.2.1

  Two new cytotoxic compounds, 2-[10(Z)-heptadecenyl]-1,4-hydroquinone (1) and (4R,6R)-dihydroxy-4-[10(Z)-heptadecenyl]-[10(Z)heptadecenyl]-2-cyclohexenone (2) have been isolated from a MeOH extract of seeds of Tapirira guianensis. The structures were established through spectral analysis of the isolates and their derivatives.