detetrahydroconidendrin | 19463-47-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: detetrahydroconidendrin
• 英文别名: 7-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1H-benzo[f][2]benzofuran-3-one
• CAS: 19463-47-9
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: JJVJBPKUTANWEW-UHFFFAOYSA-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：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 detetrahydroconidendrin 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以10 mg的产率得到dehydrodimethylconidendrin
  参考文献：
  名称：

  Five new compounds from the heartwood of Juniperus formosana Hayata.

  摘要：

  研究发现，八叶杜松的热木提取物中含有已知成分 β-谷甾醇、α-柏木醇、4-酮柏木醇、3β-羟基柏木醇、异柏木酸、δ-卡地诺醇、卡地宁-8-烯-10-醇、氯凡二醇、杉醇、Δ5-脱氢杉二醇、土他洛尔、7-氧代土他洛尔、隐酮皂苷、大黄素和甲基 α-conidendral，以及五种新化合物：7α-甲氧基脱氧隐酮皂苷、苏木精、去四氢conidendrin、福莫桑醇和桧二醇。此外，还获得了 7β-hydroxydeoxocryptojaponol （首次分离出天然产物）。通过 X 射线分析，阐明了 Junipediol 的新型倍半萜骨架。

  DOI：

  10.1248/cpb.38.3195
• 作为产物：
  描述：

  (+/-)-β-conidendrin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以44%的产率得到detetrahydroconidendrin
  参考文献：
  名称：

  Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes

  摘要：

  Positional preferences for-para benzylic oxygenation of tetrahydronaphthalenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-aqueous dioxane were investigated by comparing the tetralone products from 6-hydroxy-7-methoxy- and 6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene. The directing influence by an aromatic substituent on para benzylic oxygenation was in the order OH > OMe > OAc. Consistent with this finding were results obtained from lignan analogues. Treatment of (+)-beta-conidendryl alcohol with DDQ in dry dioxane resulted in the intramolecular bridging by one of two primary hydroxy groups to the benzylic position, giving an oxabicyclo[3.2.1]octane. Similar treatment of (+)-dimethyl-beta-conidendryl alcohol resulted in bridging by the alternate primary hydroxyl group to the benzhydrylic carbon giving an isomeric oxabicyclo[3.2.1]octane.

  DOI：

  10.1021/jo981950u

文献信息

• KUO, YUCH-HSIUNG;WU, TSENG-RONG;CHENG, MING-CHU;WANG, YU, CHEM. AND PHARM. BULL., 38,(1990) N2, C. 3195-3201
  作者：KUO, YUCH-HSIUNG、WU, TSENG-RONG、CHENG, MING-CHU、WANG, YU

  DOI：——

  日期：——
• Directed, DDQ-Promoted Benzylic Oxygenations of Tetrahydronaphthalenes
  作者：Frank D. Ramdayal、David J. Kiemle、Robert T. LaLonde

  DOI：10.1021/jo981950u

  日期：1999.6.1

  Positional preferences for-para benzylic oxygenation of tetrahydronaphthalenes by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-aqueous dioxane were investigated by comparing the tetralone products from 6-hydroxy-7-methoxy- and 6-acetoxy-7-methoxy-1,2,3,4-tetrahydronaphthalene. The directing influence by an aromatic substituent on para benzylic oxygenation was in the order OH > OMe > OAc. Consistent with this finding were results obtained from lignan analogues. Treatment of (+)-beta-conidendryl alcohol with DDQ in dry dioxane resulted in the intramolecular bridging by one of two primary hydroxy groups to the benzylic position, giving an oxabicyclo[3.2.1]octane. Similar treatment of (+)-dimethyl-beta-conidendryl alcohol resulted in bridging by the alternate primary hydroxyl group to the benzhydrylic carbon giving an isomeric oxabicyclo[3.2.1]octane.
• Five new compounds from the heartwood of Juniperus formosana Hayata.
  作者：Yueh-Hsiung KUO、Tseng-Rong WU、Ming-Chu CHENG、Yu WANG

  DOI：10.1248/cpb.38.3195

  日期：——

  Extracts of the heatwood of Juniperus formosana HAYATA were found to contain the known constituents β-sitosterol, α-cedrol, 4-ketocedrol, 3βhydroxycedrol, isocedrolic acid, δ-cadinol, cadin-8-en-10-ol, clovandiol, sugiol, Δ5-dehydrosugiol, totarol, 7-oxototarol, cryptojaponol, emodin, and methyl α-conidendral, together with five new compounds, 7α-methoxydeoxocryptojaponol, suginal, detetrahydroconidendrin, formosanol, and junipediol. In addition, 7β-hydroxydeoxocryptojaponol was obtained (first isolation as a natural product). Junipediol has a novel sesquiterpene skeleton which was elucidated by X-ray analysis.

  研究发现，八叶杜松的热木提取物中含有已知成分 β-谷甾醇、α-柏木醇、4-酮柏木醇、3β-羟基柏木醇、异柏木酸、δ-卡地诺醇、卡地宁-8-烯-10-醇、氯凡二醇、杉醇、Δ5-脱氢杉二醇、土他洛尔、7-氧代土他洛尔、隐酮皂苷、大黄素和甲基 α-conidendral，以及五种新化合物：7α-甲氧基脱氧隐酮皂苷、苏木精、去四氢conidendrin、福莫桑醇和桧二醇。此外，还获得了 7β-hydroxydeoxocryptojaponol （首次分离出天然产物）。通过 X 射线分析，阐明了 Junipediol 的新型倍半萜骨架。