(R)-3-(4-methylphenyl)butanenitrile | 192512-81-5

• 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: (R)-3-(4-methylphenyl)butanenitrile
• 英文别名: (R)-p-tolylbutyronitrile；(3R)-3-(4-methylphenyl)butanenitrile
• CAS: 192512-81-5
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: XHPJPLJBQPXNGJ-SNVBAGLBSA-N

物化性质

• 沸点：
  282.9±9.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (R)-3-(4-methylphenyl)butanenitrile 在 盐酸 、 二异丁基氢化铝 作用下， 生成 (R)-3-(p-tolyl)butanal
  参考文献：
  名称：

  New asymmetric construction of the benzylic quaternary stereogenic centre: an enantiocontrolled access to (−)-α-cuparenone

  摘要：

  通过采用一种新的不对称构建方法学，用于形成苄基四级立体中心，现已实现了(-)-α-cuparenone的高效且对映选择性的形式全合成。

  DOI：

  10.1039/a702667f
• 作为产物：
  描述：

  对甲基苯乙酸 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 氯化亚砜 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 (R)-3-(4-methylphenyl)butanenitrile
  参考文献：
  名称：

  Organic Synthesis in Pheromone Science

  摘要：

  给出了例子来说明化学和/或酶促不对称反应在合成宽角面粉甲虫、跳虫、黑加仑茎切割虫和科罗拉多土豆甲虫的新信息素中的应用。总结了信息素中立体化学与生物活性之间的关系，以强调在信息素感知中揭示的生物多样性。

  DOI：

  10.3390/10091023

文献信息

• Synthesis of (R)-ar-turmerone and its conversion to (R)-ar-himachalene, a pheromone component of the flea beetle: (R)-ar-himachalene is dextrorotatory in hexane, while levorotatory in chloroform
  作者：Kenji Mori

  DOI：10.1016/j.tetasy.2004.11.077

  日期：2005.2

  (R)-ar-Turmerone was synthesized from (4-methylphenyl)acetic acid by employing Evans asymmetric alkylation as the key step. (R)-ar-Turmerone was converted to (R)-ar-himachalene, which was dextrorotatory in hexane while levorotatory in chloroform. Enantiomerically impure (75% ee) (R)-3-(4-methylphenyl)butanoic acid crystallized more readily than the enantiomerically pure one.

  （- [R ）-芳-Turmerone，由（4-甲基苯基）乙酸通过使用埃文斯不对称烷基化作为关键步骤合成。（- [R ）-芳-Turmerone转化成（- [R ） -芳-himachalene，这是右旋的在己烷中的氯仿，同时左旋的。对映体不纯的（75％ee）（R）-3-（4-甲基苯基）丁酸比对映体纯的更容易结晶。
• Copper Hydride Catalyzed Enantioselective Conjugate Reduction of Unsaturated Nitriles
  作者：Jaesook Yun、Daehyung Lee、Youngmin Yang

  DOI：10.1055/s-2007-966068

  日期：——

  α,β-Unsaturated nitriles were reduced with high levels of enantioselectivity via copper hydride catalysis. In this procedure, bench-top stable copper(II) acetate and Josiphos ligand are used as the chiral catalyst and an inexpensive hydrosilane, polymethylhydrosiloxane (PMHS) is employed as the stoichiometric reducing agent. While the reactions are conducted at 0 °C in most cases, they also can be

  通过氢化铜催化，α,β-不饱和腈以高水平的对映选择性被还原。在此过程中，台式稳定的乙酸铜 (II) 和 Josiphos 配体用作手性催化剂，廉价的氢硅烷聚甲基氢硅氧烷 (PMHS) 用作化学计量还原剂。虽然反应在大多数情况下是在 0°C 下进行的，但它们也可以在室温下以更高的速率进行，而对映体过量没有显着下降。
• Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2011.03.012

  日期：2011.3

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Nitriles
  作者：Daehyung Lee、Daesung Kim、Jaesook Yun

  DOI：10.1002/anie.200600184

  日期：2006.4.21
• New asymmetric construction of the benzylic quaternary stereogenic centre: an enantiocontrolled access to (−)-α-cuparenone
  作者：Takamitsu Kosaka、Toshikazu Bando、Kozo Shishido

  DOI：10.1039/a702667f

  日期：——

  An efficient and enantiocontrolled formal total synthesis of (-)-α-cuparenone has been accomplished by employing a new asymmetric construction methodology for formation of the benzylic quaternary stereogenic centre.

  通过采用一种新的不对称构建方法学，用于形成苄基四级立体中心，现已实现了(-)-α-cuparenone的高效且对映选择性的形式全合成。