cadina-4,10(15)-dien-3-one | 131417-74-8

• 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: cadina-4,10(15)-dien-3-one
• 英文别名: (4Ar,5S,8aR)-3-methyl-8-methylidene-5-propan-2-yl-1,4a,5,6,7,8a-hexahydronaphthalen-2-one
• CAS: 131417-74-8
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: QUTSKAAVYUOEQA-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cadina-4,10(15)-dien-3-one 在 lanthanum(III) chloride 、 lithium aluminium tetrahydride 、 Beauveria Bassiana ATCC 7159 作用下， 以 四氢呋喃 为溶剂， 反应 336.17h， 生成 (4S)-cadina-10(15)-en-3-one
  参考文献：
  名称：

  Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159

  摘要：

  Incubation of cadina-4.10(15)-dien-3-one with Beauveria bassiana ATCC 7159 has resulted in the production of nine novel sesquiterpenes. These metabolites were identified as (4S)-cadin-10(15)-en-3-one, (4S)-3 alpha-hydroxycadin-10(15)-ene, (4R)-3 alpha-hydloxycadin-10(15)-ene, (4S)-3 beta-hydroxycadin-10(15)-ene, (4S)-3 beta-hydroxycadina-10(15),12(14)-diene, (4S)-13-hydroxycadin-10(15)-en-3-one, (4S)-12-hydroxycadin-10(15)-en-3-one, (4R)-3 beta,14-dihydroxycadin-10(15)-ene and 3 alpha-hydroxycadina-4,10(15)diene. The allylic alcohol 3 alpha-hydroxycadina-4 10(15)-diene was also biotransformed to afford cadina-4,10(15)-dien-3-one, (4S)-cadin-10(15)-en-3-one and (4S)-12-hpdroxycadin-10(15)-en-3-one. The insecticidal potential and phytotoxicity of the isolated metabolites have been evaluated, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00024-8
• 作为产物：
  描述：

  3α-hydroxycadina-4,10(15)-diene 在 Beauveria Bassiana ATCC 7159 作用下， 反应 336.0h， 以20 mg的产率得到(4S)-12-hydroxycadina-10(15)-en-3-one
  参考文献：
  名称：

  Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159

  摘要：

  Incubation of cadina-4.10(15)-dien-3-one with Beauveria bassiana ATCC 7159 has resulted in the production of nine novel sesquiterpenes. These metabolites were identified as (4S)-cadin-10(15)-en-3-one, (4S)-3 alpha-hydroxycadin-10(15)-ene, (4R)-3 alpha-hydloxycadin-10(15)-ene, (4S)-3 beta-hydroxycadin-10(15)-ene, (4S)-3 beta-hydroxycadina-10(15),12(14)-diene, (4S)-13-hydroxycadin-10(15)-en-3-one, (4S)-12-hydroxycadin-10(15)-en-3-one, (4R)-3 beta,14-dihydroxycadin-10(15)-ene and 3 alpha-hydroxycadina-4,10(15)diene. The allylic alcohol 3 alpha-hydroxycadina-4 10(15)-diene was also biotransformed to afford cadina-4,10(15)-dien-3-one, (4S)-cadin-10(15)-en-3-one and (4S)-12-hpdroxycadin-10(15)-en-3-one. The insecticidal potential and phytotoxicity of the isolated metabolites have been evaluated, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00024-8

文献信息

• Biotransformation of squamulosone by Curvularia lunata ATCC 12017
  作者：Dwight O Collins、Greg O Buchanan、William F Reynolds、Paul B Reese

  DOI：10.1016/s0031-9422(01)00060-7

  日期：2001.6

  Squamulosone (aromadendr-1(10)-en-9-one). isolated in large quantity from the plant Hyptis verticillata Jacq. (Labiatae), was incubated with the fungus Curvularia lunata ATCC 12017 in two different growth media. Six metabolites were isolated from each medium, with five of the products being common to both fermentations. All seven metabolites are novel. The insecticidal activity of these aromadendranes was evaluated against the sweet potato weevil Cylas formicarius elegantulus. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Biotransformation of cadina-4,10(15)-dien-3-one and 3α-hydroxycadina-4,10(15)-diene by Curvularia lunata ATCC 12017
  作者：Dwight O Collins、Paul B Reese

  DOI：10.1016/s0031-9422(01)00487-3

  日期：2002.3

  Cadina-4,10(15)-dien-3-one (1) was metabolised by Curvularia lunata ATCC 12017 in two different growth media to give three metabolites, one of which, 12-hydroxycadina-4,10(15)-dien-3-one (4), was new. Incubation of 3a-hydroxycadina-4,10(15)-diene (2) with the fungus produced three new analogues, namely, (4S)-1alpha,3alpha-dihydroxycadin-10(15)-ene (5), 3alpha,14-dihydroxycadina-4,10(15)diene (6) and 3alpha, 12-dihydroxycadina-4,10(15)-diene (7). (C) 2002 Elsevier Science Ltd. All rights reserved.