(E)-5,9-dimethyldeca-4,8-dienenitrile | 35219-81-9

• 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)-5,9-dimethyldeca-4,8-dienenitrile
• 英文别名: geranyl acetonitrile；homogeranyl cyanide；trans-Homogeranylcyanid；Geranylacetonitril；(4E)-5,9-dimethyl-4,8-decadienenitrile；(4E)-5,9-dimethyldeca-4,8-dienenitrile
• CAS: 35219-81-9；5579-62-4
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: JJNRLLWEOZKYJE-XYOKQWHBSA-N

物化性质

• 沸点：
  295.0±19.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-5,9-dimethyldeca-4,8-dienenitrile 在 吡啶 、 氢氧化钾 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 氯化亚砜 、 四溴环己二烯-1-酮 、 硼烷 、 双氧水 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (5R,6S,9S)-3-(2-hydroxypropan-2-yl)-6-methyl-9-prop-1-en-2-yl-1-oxaspiro[4.4]nonan-2-one
  参考文献：
  名称：

  Synthesis of Curcumanolide A, a Unique Spirolactone Sesquiterpene

  摘要：

  利用 Br+ 诱导的环化和随后的缩环法，通过 11 个步骤从高香叶基氰化物合成了外消旋形式的螺环内酯--莪术内酯 A。

  DOI：

  10.1246/cl.1992.2343
• 作为产物：
  描述：

  5-溴-2-甲基-2-戊烯 在 氢溴酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (E)-5,9-dimethyldeca-4,8-dienenitrile
  参考文献：
  名称：

  Julia,M. et al., Bulletin de la Societe Chimique de France, 1960, p. 1072 - 1079

  摘要：

  DOI：

文献信息

• ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE
  申请人：Miyagi Yukino

  公开号：US20140171675A1

  公开（公告）日：2014-06-19

  The invention relates to an isoprene oligomer that contains a trans structural moiety and a cis structural moiety, which can be represented by the following formula (1), wherein at least 1 atom or group in the trans structural moiety is replaced by another atom or group. The invention also relates to a polyisoprene, which is biosynthesized using the isoprene oligomer and isopentenyl diphosphate. Further, this invention provides a rubber composition comprising the isoprene oligomer and/or the polyisoprene, and a pneumatic tire, including tire components (e.g., treads and sidewalls) formed from the rubber composition. wherein n represents an integer from 1 to 10; m represents an integer from 1 to 30; and Y represents a hydroxy group, a formyl group, a carboxy group, an ester group, a carbonyl group, or a group represented by the following formula (2):

  该发明涉及一种含有反式结构基团和顺式结构基团的异戊二烯寡聚物，可以用以下公式（1）表示，其中反式结构基团中至少有1个原子或基团被另一个原子或基团取代。该发明还涉及一种聚异戊二烯，它是使用异戊二烯寡聚物和异戊二烯二磷酸盐生物合成的。此外，该发明提供了一种橡胶组合物，包括异戊二烯寡聚物和/或聚异戊二烯，以及一种充气轮胎，其中轮胎组件（例如胎面和侧壁）由该橡胶组合物形成。 其中n表示1到10之间的整数；m表示1到30之间的整数；Y表示一个羟基、一个甲酰基、一个羧基、一个酯基、一个酰基或由以下公式（2）表示的基团。
• Deceptive Complexity in Formation of Cleistantha-8,12-diene
  作者：Jin Liang、Amy T. Merrill、Croix J. Laconsay、Anwei Hou、Qingyu Pu、Jeroen S. Dickschat、Dean J. Tantillo、Qiang Wang、Reuben J. Peters

  DOI：10.1021/acs.orglett.2c00680

  日期：2022.4.15

  A barley diterpene synthase (HvKSL4) was found to produce (14S)-cleistantha-8,12-diene (1). Formation of the nearly planar cyclohexa-1,4-diene configuration leaves the ring poised for aromatization, but necessitates a deceptively complicated series of rearrangements steered through a complex energetic landscape, as elucidated here through quantum chemical calculations and labeling studies.

  发现大麦二萜合酶 (HvKSL4) 可产生 (14 S )-cleistantha-8,12-二烯 ( 1 )。近乎平面的 cyclohexa-1,4-diene 构型的形成使环为芳构化做好了准备，但需要通过复杂的能量景观进行一系列看似复杂的重排，如本文通过量子化学计算和标记研究所阐明的那样。
• A Stereoselective Hydroamination Transform To Access Polysubstituted Indolizidines
  作者：Sergey V. Pronin、M. Greg Tabor、Daniel J. Jansen、Ryan A. Shenvi

  DOI：10.1021/ja211090n

  日期：2012.2.1

  Stereoselective, intramolecular, formal hydroamination of dienamines via directed hydroboration is reported. Four stereocenters are set in the process. Natural and unnatural indolizidine alkaloids can be synthesized from simple unsaturated amines using the title process.
• Influence of heterocyclic and oxime-containing farnesol analogs on quorum sensing and pathogenicity in Candida albicans
  作者：Roman Shchepin、Dhammika H.M.L.P. Navarathna、Raluca Dumitru、Shane Lippold、Kenneth W. Nickerson、Patrick H. Dussault

  DOI：10.1016/j.bmc.2007.11.011

  日期：2008.2.15

  A series of synthetic molecules combining a geranyl backbone with a heterocyclic or oxime head group are quorum-sensing molecules that block the yeast to mycelium transition in the dimorphic fungus Candida albicans. A number of the analogs have an IC50 <= 10 mu M, a level of potency essentially identical to the natural quorum sensing signal, the sesquiterpene farnesol. Two of the most potent analogs, neither toxic toward healthy mice, display remarkably different effects when co-administered with C. albicans. While neither offers protection from candidiasis, one analog mimics farnesol in acting as a virulence factor, whereas the other has no effect. The results offer the first example of highly potent synthetic fungal quorum-sensing molecules, and provide the first evidence for the ability to decouple quorum sensing and virulence. (C) 2007 Elsevier Ltd. All rights reserved.
• One-step synthesis of γ-δ-unsaturated nitriles from allylic halides using cyanomethylcopper
  作者：E.J. Corey、Isao Kuwajima

  DOI：10.1016/s0040-4039(01)84357-4

  日期：1972.1