3-(3,7,11-trimethyldodeca-2,6,10-trienyl)-1H-indole | 102720-33-2

• 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: 3-(3,7,11-trimethyldodeca-2,6,10-trienyl)-1H-indole
• 英文别名: 3-farnesylindole；farnesylindole；3-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-1H-indole；3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-1H-indole
• CAS: 102720-33-2
• 化学式: C₂₃H₃₁N
• 分子量: 321.506
• InChiKey: GIEWHHJZPKZOFH-NKFKFSAASA-N

物化性质

• 沸点：
  479.7±24.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(3,7,11-trimethyldodeca-2,6,10-trienyl)-1H-indole 在 E_. coli BL₂₁(DE₃)/pCSG₂₆₀₉ mutant 、 卡那霉素碱 作用下， 反应 20.0h， 生成 3-(epoxyfarnesyl)indole
  参考文献：
  名称：

  Elucidating the Cyclization Cascades in Xiamycin Biosynthesis by Substrate Synthesis and Enzyme Characterizations

  摘要：

  Indolosesquiterpene xiamycin A features a pentacyclic core structure. The chemical synthesis of two key precursors, 3-farnesylindole and 3-(epoxyfarnesyl)-indole, allowed elucidation of the enzymatic cascades forming the pentacyclic ring system of xiamycin A by XiaO-catalyzed epoxidation and the membrane protein XiaH-catalyzed terpene cyclization. The substrate flexibility of XiaI, an indole oxygenase for assembly of the central ring, was also demonstrated.

  DOI：

  10.1021/ol503399b
• 作为产物：
  描述：

  吲哚 、 反,反-法呢基溴 在 四丁基碘化铵 、 zinc trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以49%的产率得到3-(3,7,11-trimethyldodeca-2,6,10-trienyl)-1H-indole
  参考文献：
  名称：

  Regioselective Synthesis of 3-Alkylindoles Mediated by Zinc Triflate

  摘要：

  Zinc triflate was found to be an effective reagent for the C3-alkylation of indoles by alkyl halides in the presence of Hunig's base and tetrabutylammonium iodide. This new method for indole alkylation proceeds by a S(N)1-like pathway, and is general for allylic, benzylic, and tertiary halides.

  DOI：

  10.1021/jo010996b

文献信息

• Synthesis of 3-ω-epoxido farnesyl indoles, intermediates in the biogenesis of sesquiterpenic indole alkaloids
  作者：Catherine Mirand、Michèle Döé de Maindreville、Jean Lévy

  DOI：10.1016/s0040-4039(00)98704-5

  日期：1985.1

  Epoxides 1a,b, the probable bioprecursors of a serie of indoloterpene alkaloids, were synthezised from indole and farnesyl bromides through application of the Van Tamelen regiospecific epoxidation process to the derived N-acylindolines 14a,b.

  通过将Van Tamelen区域特异性环氧化过程应用于衍生的N-酰基环吲哚14a，b，从吲哚和法呢基溴合成了一系列的吲哚并萜烯生物碱的环氧化合物1a，b。
• Nodulisporic acid E biosynthesis: <i>in vivo</i> characterisation of NodD1, an indole-diterpene prenyltransferase that acts on an emindole SB derived indole-diterpene scaffold
  作者：Kyle C. Van de Bittner、Rosannah C. Cameron、Leyla Y. Bustamante、Rudranuj Bundela、Sarah A. Kessans、Jan Vorster、Matthew J. Nicholson、Emily J. Parker

  DOI：10.1039/c9md00143c

  日期：——

  Prenylation of aromatic compounds is a key tailoring reaction in biosynthesis of bioactive indole-diterpenes. Here, we identify NodD1 as the enzyme responsible for the bisprenylation of nodulisporic acid F. This prenyltransferase showed a preference for its natural indole-diterpene substrate whereas other related enzymes were not able to catalyse this conversion.

  芳香族化合物的异戊二烯化是生物活性吲哚二萜生物合成中的关键定制反应。在这里，我们将 NodD1 确定为负责球孢酸 F 双异戊二烯化的酶。这种异戊烯基转移酶显示出对其天然吲哚二萜底物的偏好，而其他相关酶无法催化这种转化。
• Rice Bran Extracts for Inflammation and Methods of Use Thereof
  申请人：Alberte Randall S.

  公开号：US20090285919A1

  公开（公告）日：2009-11-19

  The present invention relates in part to stabilized rice bran extracts enriched in compounds that have inhibitory activity against certain anti-inflammatory therapeutic endpoints, such as the COX-1, COX-2 and 5-LOX enzymes. Another aspect of the invention relates to pharmaceutical compositions comprising the extracts and to methods of treating inflammatory diseases comprising administering the aforementioned extracts.
• Regioselective Synthesis of 3-Alkylindoles Mediated by Zinc Triflate
  作者：Xiuwen Zhu、A. Ganesan

  DOI：10.1021/jo010996b

  日期：2002.4.1

  Zinc triflate was found to be an effective reagent for the C3-alkylation of indoles by alkyl halides in the presence of Hunig's base and tetrabutylammonium iodide. This new method for indole alkylation proceeds by a S(N)1-like pathway, and is general for allylic, benzylic, and tertiary halides.
• Elucidating the Cyclization Cascades in Xiamycin Biosynthesis by Substrate Synthesis and Enzyme Characterizations
  作者：Huixian Li、Yu Sun、Qingbo Zhang、Yiguang Zhu、Shu-Ming Li、Ang Li、Changsheng Zhang

  DOI：10.1021/ol503399b

  日期：2015.1.16

  Indolosesquiterpene xiamycin A features a pentacyclic core structure. The chemical synthesis of two key precursors, 3-farnesylindole and 3-(epoxyfarnesyl)-indole, allowed elucidation of the enzymatic cascades forming the pentacyclic ring system of xiamycin A by XiaO-catalyzed epoxidation and the membrane protein XiaH-catalyzed terpene cyclization. The substrate flexibility of XiaI, an indole oxygenase for assembly of the central ring, was also demonstrated.