(Z)-Undec-9-enenitrile | 131379-24-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-Undec-9-enenitrile
• 英文别名: 9-undecenenitrile；9-Undecenenitrile, (9Z)-
• CAS: 131379-24-3
• 化学式: C₁₁H₁₉N
• 分子量: 165.279
• InChiKey: RPLWLQJSZFPHGM-IHWYPQMZSA-N

物化性质

• LogP：
  3.842 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  cis-8-undecenaldoxime 在 Sn_1.9WClO_6.3*9H₂O 作用下， 以 邻二甲苯 为溶剂， 149.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以95%的产率得到(Z)-Undec-9-enenitrile
  参考文献：
  名称：

  钨锡混合氢氧化物作为有效的多相催化剂，用于醛肟的脱水成腈。

  摘要：

  DOI：

  10.1002/anie.200605004

文献信息

• METHOD FOR THE CONTROLLED HYDROFORMYLATION AND ISOMERIZATION OF A NITRILE/ESTER/OMEGA UNSATURATED FATTY ACID
  申请人：ARKEMA FRANCE

  公开号：US20160115120A1

  公开（公告）日：2016-04-28

  A method to synthesize a fatty nitrile/ester aldehyde comprising the following steps: 1) hydroformylation of a ω-unsaturated fatty nitrile/ester/acid substrate under particular conditions of partial pressure, temperature, reaction time, conversion rate of the ω-unsaturated fatty nitrile/ester/acid reactant, catalyst, [substrate]/[metal] molar ratio and [ligand]/[metal] molar ratio so as after the reaction to obtain: a hydroformylation product comprising at least one fatty nitrile/ester/acid aldehyde of formula: OHC—(CH 2 ) r+2 —R, and an isomerate comprising at least one fatty nitrile/ester/acid isomer with internal unsaturation in which at least 80% of the internal isomer(s) of the isomerate are formed of the ω-1 unsaturated isomer of formula CH 3 —CH═CH—(CH 2 ) r−1 —R; followed by: 2) separation and recovery of the fatty nitrile/ester/acid aldehyde and of the isomerate.

  一种合成脂肪酸腈/酯醛的方法，包括以下步骤： 1）在特定的分压、温度、反应时间、ω-不饱和脂肪酸腈/酯/酸底物的转化率、催化剂、[底物]/[金属]摩尔比和[配体]/[金属]摩尔比条件下，对ω-不饱和脂肪酸腈/酯/酸底物进行氢甲酰化反应，以便在反应后获得： a. 一个氢甲酰化产物，包括至少一种公式为 OHC—(CH2)r+2—R 的脂肪酸腈/酯/酸醛；和 b. 一个异构物，包括至少一种具有内部不饱和的脂肪酸腈/酯/酸异构体，其中至少80%的内部异构体是由公式为 CH3—CH═CH—(CH2)r−1—R 的ω-1不饱和异构体形成的；随后进行： 2）分离和回收脂肪酸腈/酯/酸醛和异构物。
• Rhodium versus Iridium Catalysts in the Controlled Tandem Hydroformylation-Isomerization of Functionalized Unsaturated Fatty Substrates
  作者：Jérémy Ternel、Jean-Luc Couturier、Jean-Luc Dubois、Jean-François Carpentier

  DOI：10.1002/cctc.201402783

  日期：2015.2

  10‐undecenitrile (1) and related unsaturated fatty substrates (H2CCH(CH2)7CH2R; R=CO2Me, CH2Br, CHO) has been studied with rhodium, iridium, ruthenium, and palladium biphephos catalysts. The reactions proceeded effectively with all four systems, with high selectivities for the linear aldehyde (ratio of linear/branched aldehydes=99:1). The biphephos‐bis[chloro(cyclooctadiene)iridium] system showed a non‐optimized

  10 undecenitrile（的加氢甲酰化1）和相关的不饱和脂肪酸底物（H 2 CCH（CH 2）7 CH 2 R等R = CO 2 Me中的CH 2 BR，CHO）已经研究了铑，铱，钌，以及二苯醚钯催化剂。该反应在所有四个系统中均有效地进行，对线性醛具有高选择性（线性/支化醛的比率= 99：1）。Biphephos-双[氯（环辛二烯）铱]系统显示出未优化的加氢甲酰化转化频率（TOF HF）为770 h -1，仅比基于铑的系统（TOF HF）低约5倍= 3320 h -1）; 钯和钌联苯双酚体系的活性较低（TOF HF分别为210和310 h -1）。通过回收利用，在两种情况下均实现了卓越的生产率（TON≈58000 mol（1 / 1- int）mol（Ir）-1和250 000 mol（1 / 1- int）mol（Rh）-1，其中int＝内部烯烃）。这些催化剂使末端烯烃竞争异构
• The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, .alpha.,.beta.-unsaturated ketones, and allylic, aryl, and vinyl halides
  作者：Lishan Zhu、Richard M. Wehmeyer、Reuben D. Rieke

  DOI：10.1021/jo00004a021

  日期：1991.2

  Highly reactive zinc, prepared by the lithium naphthalenide reduction of ZnCl2, readily undergoes oxidative addition to alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds in excellent yields. Significantly, the reaction will tolerate a spectrum of functional groups on the organic halides. Accordingly, this approach can now be used to prepare a wide variety of highly functionalized organozinc compounds. In the presence of Cu(I) salts, the organozinc compounds cross-couple with acid chlorides, conjugatively add to alpha,beta-unsaturated ketones, and regioselectively undergo S(N)2' substitution reactions with allylic halides. They also cross-couple with aryl or vinyl halides with Pd(0) catalysts.
• A Tungsten–Tin Mixed Hydroxide as an Efficient Heterogeneous Catalyst for Dehydration of Aldoximes to Nitriles
  作者：Kazuya Yamaguchi、Hiroshi Fujiwara、Yoshiyuki Ogasawara、Miyuki Kotani、Noritaka Mizuno

  DOI：10.1002/anie.200605004

  日期：2007.5.18