(E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol | 434955-77-8

• 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: (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol
• 英文别名: 10,11-dihydroxynerolidol；1.6-Farnesadiene-3.10.11-triol；(6E)-2,6,10-trimethyldodeca-6,11-diene-2,3,10-triol
• CAS: 434955-77-8；622347-72-2
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: BGUYVWYUIXKRDO-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以80%的产率得到(E)-8-hydroxy-4,8-dimethyl-deca-4,9-dienal
  参考文献：
  名称：

  Cyclonerodiol biosynthesis and the enzymic conversion of farnesyl to nerolidyl pyrophosphate

  摘要：

  DOI：

  10.1021/ja00394a032
• 作为产物：
  描述：

  香叶基丙酮 在 高氯酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 10.25h， 生成 (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol
  参考文献：
  名称：

  Cyclonerodiol biosynthesis and the enzymic conversion of farnesyl to nerolidyl pyrophosphate

  摘要：

  DOI：

  10.1021/ja00394a032

文献信息

• Asymmetric dihydroxylation of linalool, nerolidol and citronellyl acetate. Enantioselective synthesis of (3S, 6S)-tetrahydro-2,2,6-trimethyl-6-vinyl-2H-pyran-3-ol
  作者：Giovanni Vidari、Andrea Giori、Antonella Dapiaggi、Gianluigi Lanfranchi

  DOI：10.1016/s0040-4039(00)91832-x

  日期：1993.10

  The asymmetric Sharpless' dihydroxylation of linalool, citronellyl acetate and nerolidol was investigated. High diastereo-. enantio- and positional selectivity was observed for the first two terpenes. A highly diastereo- and enantioselective synthesis of (3S,6S)-tetrahydro- 2,2,6-trimethyl - 6-vinyl-2H -pyran-3-ol is described.
• Biotransformations of Acyclic Terpenoids, (±)-<i>trans</i>-Nerolidol and Geranylacetone, by <i>Glomerella </i><i>cingulata</i>
  作者：Mitsuo Miyazawa、Hirokazu Nankai、Hiromu Kameoka

  DOI：10.1021/jf950464u

  日期：1996.1.1

  Microbial transformations of (+/-)-trans-nerolidol and geranylacetone were carried out with a plant pathogenic fungus, Glomerella cingulata. (+/-)-trans-Nerolidol and geranylacetone were hydrated at a remote double bond as the main metabolic pathway. A large amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,11-diol and small amount of(E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol were obtained from (+/-)-trans-nerolidol. Geranylacetone was transformed to (E)-10-hydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. (E)-9,10-Dihydroxy-6,10-dimethyl-5-undecen-2-one, (E)-6,10-dimethyl-5,9-undecadien-2-ol, (E)-6,10-dimethyl-5-undecene-2,9,10-trio and (E)-6,10-dimethyl-5-undecene-2,10-diol were also obtained from geranylacetone. The structures of metabolic products were determined by spectroscopic data.
• Madyastha, K M; Gururaja, T L, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 609 - 614
  作者：Madyastha, K M、Gururaja, T L

  DOI：——

  日期：——
• HOLMES, DUNCAN S.;ASHWORTH, DEREEN M.;ROBINSON, JOHN A., HELV. CHIM. ACTA, 73,(1990) N, C. 260-271
  作者：HOLMES, DUNCAN S.、ASHWORTH, DEREEN M.、ROBINSON, JOHN A.

  DOI：——

  日期：——
• Cyclonerodiol biosynthesis and the enzymic conversion of farnesyl to nerolidyl pyrophosphate
  作者：David E. Cane、Radha Iyengar、Ming-Shi Shiao

  DOI：10.1021/ja00394a032

  日期：1981.2