[(4bS,8aS,9S)-3-hydroxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-9-yl] acetate | 190721-59-6

• 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: [(4bS,8aS,9S)-3-hydroxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-9-yl] acetate
• CAS: 190721-59-6
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: DKFWEVHDRVCABW-JAXLGGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(4bS,8aS,9S)-3-hydroxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-9-yl] acetate 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 6α-hydroxyferruginol
  参考文献：
  名称：

  6-Oxoferruginol and 6α-Acetoxyferruginol, New Abietane-Type Diterpenes from the Heartwood of Juniperus formosana

  摘要：

  New abietane diterpenes, 6 alpha-acetoxyferruginol and 6-oxoferruginol were isolated from the heartwood of Juniperus formosana Hay. var. concolor Hay. together with the known compounds ferruginol, sugiol, xanthoperol, 5-epi-xanthoperol, and 6,12-'dihydroxyabieta-5,8,11,13-tetraen-7-one. The structures of the new compounds were elucidated on the basis of spectral and chemical evidence.

  DOI：

  10.1021/np960389x
• 作为产物：
  描述：

  6α-hydroxy-7-oxoferruginol 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 43.0h， 生成 [(4bS,8aS,9S)-3-hydroxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-9-yl] acetate
  参考文献：
  名称：

  Diterpenes from the Heartwood of Juniperus formosana HAY. var. concolr HAY.

  摘要：

  从杜松（Juniperus formosana HAY. var. concolor HAY）的心材中分离出了三种二萜，即 6β-hydroxyferruginol (1a)、formosaninol (2a) 和 formosanin (2b)。根据光谱分析和化学证据，推断出福尔马林醇的结构是一种具有 6-O-7' 和 7-O-6' 连接的二聚铁杉醇。福尔马林是福尔马林醇的二甲醚。6α-Hydroxy-7-oxoferruginol 可通过氢化铝锂还原和酸化转化为 6α- 和 6β-hydroxyferruginols、6-oxoferruginol 和 formosaninol。从隐花中分离出的 6β-hydroxyferruginol 的结构被修正为 6α-hydroxyferruginol 。

  DOI：

  10.1248/cpb.44.1431

文献信息

• 6-Oxoferruginol and 6α-Acetoxyferruginol, New Abietane-Type Diterpenes from the Heartwood of <i>Juniperus formosana</i>
  作者：Yueh-Hsiung Kuo、Ming-Tsang Yu

  DOI：10.1021/np960389x

  日期：1997.6.1

  New abietane diterpenes, 6 alpha-acetoxyferruginol and 6-oxoferruginol were isolated from the heartwood of Juniperus formosana Hay. var. concolor Hay. together with the known compounds ferruginol, sugiol, xanthoperol, 5-epi-xanthoperol, and 6,12-'dihydroxyabieta-5,8,11,13-tetraen-7-one. The structures of the new compounds were elucidated on the basis of spectral and chemical evidence.
• Diterpenes from the Heartwood of Juniperus formosana HAY. var. concolr HAY.
  作者：Yueh-Hsiung KUO、Ming-Tsang YU

  DOI：10.1248/cpb.44.1431

  日期：——

  Three was diterpenes, 6β-hydroxyferruginol (1a), formosaninol (2a), and formosanin (2b), were isolated from the heartwood of Juniperus formosana HAY. var. concolor HAY. The structure of formosaninol was deduced to be a dimeric ferruginol with 6-O-7' and 7-O-6' linkages on the basis of spectroscopic analysis and chemical evidence. Formosanin was a dimethyl ether of formosaninol. 6α-Hydroxy-7-oxoferruginol can be converted to 6α- and 6β-hydroxyferruginols, 6-oxoferruginol and formosaninol by lithium aluminum hydride reduction and acidification. The structure of 6β-hydroxyferruginol isolated from Cryptomeria japonica was revised to 6α-hydroxyferruginol.

  从杜松（Juniperus formosana HAY. var. concolor HAY）的心材中分离出了三种二萜，即 6β-hydroxyferruginol (1a)、formosaninol (2a) 和 formosanin (2b)。根据光谱分析和化学证据，推断出福尔马林醇的结构是一种具有 6-O-7' 和 7-O-6' 连接的二聚铁杉醇。福尔马林是福尔马林醇的二甲醚。6α-Hydroxy-7-oxoferruginol 可通过氢化铝锂还原和酸化转化为 6α- 和 6β-hydroxyferruginols、6-oxoferruginol 和 formosaninol。从隐花中分离出的 6β-hydroxyferruginol 的结构被修正为 6α-hydroxyferruginol 。