5,5-dimethylhex-2-enenitrile | 357166-76-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5,5-dimethylhex-2-enenitrile
• 英文别名: 5,5-Dimethylhex-2-enenitrile
• CAS: 357166-76-8
• 化学式: C₈H₁₃N
• 分子量: 123.198
• InChiKey: RUWJJIJENZKKDA-UHFFFAOYSA-N

物化性质

• 沸点：
  179.2±9.0 °C(predicted)
• 密度：
  0.834±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  5,5-dimethylhex-2-enenitrile 在 Mn(dpm)3 苯硅烷 、 氧气 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 以27%的产率得到2-Hydroxy-5,5-dimethyl-hexanenitrile
  参考文献：
  名称：

  Direct conversion of α,β-unsaturated nitriles into cyanohydrins using Mn(dpm)3 catalyst, dioxygen and phenylsilane

  摘要：

  Treatment of alpha,beta -unsaturated nitriles with Mn(dpm)(3) (3 mol%), PhSiH3 in isopropyl alcohol in the presence of oxygen resulted in reduction and alpha- and beta -hydroxylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00693-1
• 作为产物：
  描述：

  4-Bromo-3,3-dimethyl-butyraldehyde 在 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 5,5-dimethylhex-2-enenitrile
  参考文献：
  名称：

  Acceleration of the 4-exo radical cyclization to a synthetically useful rate. Cyclization of the 2,2-dimethyl-5-cyano-4-pentenyl radical

  摘要：

  DOI：

  10.1016/s0040-4039(00)89002-4

文献信息

• <i>Z</i> ‐Selective α‐Arylation of α,β‐Unsaturated Nitriles via [3,3]‐Sigmatropic Rearrangement
  作者：Mengyuan Chen、Yuchen Liang、Taotao Dong、Weijian Liang、Yanping Liu、Yage Zhang、Xin Huang、Lichun Kong、Zhi‐Xiang Wang、Bo Peng

  DOI：10.1002/anie.202010740

  日期：2021.2

  The Morita‐Baylis–Hillman (MBH) reaction and [3, 3]‐sigmatropic rearrangement are two paradigms in organic synthesis. We have merged the two types of reactions to achieve [3,3]‐rearrangement of aryl sulfoxides with α,β‐unsaturated nitriles. The reaction was achieved by sequentially treating both coupling partners with electrophilic activator (Tf2O) and base, offering an effective approach to prepare

  Morita-Baylis-Hillman（MBH）反应和[3，3]-σ重排是有机合成的两个范例。我们将两种类型的反应合并在一起，以实现[3,3]-芳基亚砜与α，β-不饱和腈的重排。该反应是通过依次用亲电子活化剂（Tf 2 O）和碱处理两个偶合伙伴而实现的，提供了一种有效的方法，可通过直接的α-C-H芳基化制备具有Z-选择性的合成型多功能α-芳基α，β-不饱和腈未改性的α，β-不饱和腈 控制实验和DFT计算支持四个阶段的反应序列，包括Tf 2的组装O活化的芳基亚砜，具有α，β-不饱和腈，类似MBH的Lewis碱，[3,3]-重排和E1cB-消除。在这些阶段中，路易斯碱的加成是非对映选择性的，而E1cB-消除是顺式选择性的，这可能说明了反应的显着Z选择性。
• [EN] 5, 7-SUBSTITUTED-IMIDAZO [1, 2-C] PYRIMIDINES AS INHIBITORS OF JAK KINASES<br/>[FR] [1,2-C]PYRIMIDINES 5,7-IMIDAZO-SUBSTITUÉES COMME INHIBITEURS DE JAK KINASES
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2011130146A1

  公开（公告）日：2011-10-20

  Compounds of Formula I: (Formula should be inserted here) and stereoisomers and pharmaceutically acceptable salts and solvates thereof in which R1, R2, R3, R4, R5, R6, R7, X1 and X2 have the meanings given in the specification, are inhibitors of one or more JAK kinases and are useful in the treatment of autoimmune diseases, inflammatory diseases, rejection of transplanted organs, tissues and cells, as well as hematologic disorders and malignancies and their co-morbidities.

  化合物的化学式I：（应在此处插入化学式），以及其立体异构体和药学上可接受的盐和溶剂化合物，其中R1、R2、R3、R4、R5、R6、R7、X1和X2的含义如规范中所述，是一种或多种JAK激酶的抑制剂，并且在治疗自身免疫疾病、炎症性疾病、移植器官、组织和细胞的排斥反应、以及血液学紊乱和恶性肿瘤及其共病症方面具有用处。
• 5,7-substituted-imidazo[1,2-C]pyrimidines as inhibitors of JAK kinases
  申请人：Burgess Laurence E.

  公开号：US08962596B2

  公开（公告）日：2015-02-24

  Compounds of Formula I: and stereoisomers and pharmaceutically acceptable salts and solvates thereof in which R1, R2, R3, R4, R5, R6, R7, X1 and X2 have the meanings given in the specification, are inhibitors of one or more JAK kinases and are useful in the treatment of autoimmune diseases, inflammatory diseases, rejection of transplanted organs, tissues and cells, as well as hematologic disorders and malignancies and their co-morbidities.

  公式I的化合物及其立体异构体和药学上可接受的盐和溶剂化合物，其中R1、R2、R3、R4、R5、R6、R7、X1和X2的含义如规范中所述，是一种或多种JAK激酶的抑制剂，可用于治疗自身免疫疾病、炎症性疾病、移植器官、组织和细胞的排斥反应，以及血液学疾病和恶性肿瘤及其共病症。
• 5,7-SUBSTITUTED-IMIDAZO[1,2-C]PYRIMIDINES AS INHIBITORS OF JAK KINASES
  申请人：Burgess Laurence E.

  公开号：US20130131039A1

  公开（公告）日：2013-05-23

  Compounds of Formula I: (Formula should be inserted here) and stereoisomers and pharmaceutically acceptable salts and solvates thereof in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , X 1 and X 2 have the meanings given in the specification, are inhibitors of one or more JAK kinases and are useful in the treatment of autoimmune diseases, inflammatory diseases, rejection of transplanted organs, tissues and cells, as well as hematologic disorders and malignancies and their co-morbidities.

  化合物I的公式为（应在此处插入公式），其立体异构体及其药学上可接受的盐和溶剂化物均为JAK激酶的抑制剂，可用于治疗自身免疫性疾病、炎症性疾病、移植器官、组织和细胞的排斥反应，以及血液学疾病和恶性肿瘤及其共病症的治疗。其中，R1、R2、R3、R4、R5、R6、R7、X1和X2的含义如规范中所述。
• Acceleration of the 4-exo radical cyclization to a synthetically useful rate. Cyclization of the 2,2-dimethyl-5-cyano-4-pentenyl radical
  作者：Seung-Un Park、Thomas R. Varick、Martin Newcomb

  DOI：10.1016/s0040-4039(00)89002-4

  日期：——