2-isopropyl-3-oxo-3-phenylpropanenitrile | 7391-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-isopropyl-3-oxo-3-phenylpropanenitrile
• 英文别名: 2-benzoyl-3-methylbutanenitrile
• CAS: 7391-32-4
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: ABDAVEXHUNVRLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-isopropyl-3-oxo-3-phenylpropanenitrile 在 sodium hydroxide 、 钾硼氢 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 erythro-3-Hydroxy-2-isopropyl-3-phenyl-propionsaeure-amid
  参考文献：
  名称：

  Canceill,J.; Jacques,J., Bulletin de la Societe Chimique de France, 1970, p. 2180 - 2187

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[amino(phenyl)methylidene]-3-methylbutanenitrile 在 硫酸 作用下， 生成 2-isopropyl-3-oxo-3-phenylpropanenitrile
  参考文献：
  名称：

  有机锌-α-溴腈：III。相对于腈重新活化

  摘要：

  根据所用方法，有机锌化合物与腈的缩合可生成β-酮腈或酮丁腈。当起始腈为芳族化合物时，以及在α-溴异丁腈的情况下，观察到的氮化合物与β-内酰胺腈类似。

  DOI：

  10.1016/s0022-328x(00)95165-9

文献信息

• Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives
  作者：Kensuke Kiyokawa、Takaya Nagata、Satoshi Minakata

  DOI：10.1002/anie.201605445

  日期：2016.8.22

  highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N‐cyano‐N‐phenyl‐p‐toluenesulfonamide (NCTS) and p‐toluenesulfonyl cyanide (TsCN), is reported. Various β‐ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of β‐ketonitriles containing

  据报道，使用现成的氰化试剂N-氰基-N-苯基-对甲苯磺酰胺（NCTS）和对甲苯磺酰氰（TsCN）可以实现烯醇硼的高效亲电氰化。通过该新方案制备了各种β-乙腈，与现有方法相比，其具有显着广泛的底物范围。本方法还可以有效合成含有季碳原子中心的β-乙腈。另外，描述了使用手性烯醇硼用于对映选择性氰化反应的初步结果。
• Asymmetric Transfer Hydrogenation of α-Substituted-β-Keto Carbonitriles via Dynamic Kinetic Resolution
  作者：Fangyuan Wang、Tilong Yang、Ting Wu、Long-Sheng Zheng、Congcong Yin、Yongjie Shi、Xiang-Yu Ye、Gen-Qiang Chen、Xumu Zhang

  DOI：10.1021/jacs.0c13273

  日期：2021.2.17

  A catalytic protocol for the enantio- and diastereoselective reduction of α-substituted-β-keto carbonitriles is described. The reaction involves a DKR-ATH process with the simultaneous construction of β-hydroxy carbonitrile scaffolds with two contiguous stereogenic centers. A wide range of α-substituted-β-keto carbonitriles were obtained in high yields (94%–98%) and excellent enantio- and diastereoselectivities

  描述了用于α-取代的-β-酮腈的对映体和非对映体选择性还原的催化方案。该反应涉及DKR-ATH方法，该方法同时构建具有两个连续的立体异构中心的β-羟基甲腈支架。以高产率（94％–98％）和出色的对映和非对映选择性（高达> 99％ee，高达> 99：1 dr）获得了多种α-取代-β-酮腈。非对映选择性的起源也通过DFT计算得到了合理化。此外，这种方法可以快速获得异戊ox酮和他喷他多的药物中间体。
• 2-Carbonyl-3-hydroxy-alkenonitriles, their use as anti-arthritic agents and processes for their preparation
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0016277A1

  公开（公告）日：1980-10-01

  There are disclosed 2-carbonyl- 3-hydroxy-2- alkenonit- riles, their use as anti-arthritic agents and processes for their preparation. The active compounds have the formula: wherein n is an integer from 1 to 3 inclusive; M is hydrogen or a pharmaceutically acceptable cation; R6 is an alkyl group of 1 to 4 carbons; R" is one of the following aromatic groups: (1) the group in which R1, R2, R3, R4 and Ri are the same or different and are ) hydrogen, halogen, alkyl having up to 4 carbons, alkoxy having up to 4 carbons, trifluoromethyl or trichloromethyl, with the proviso that when m is the number 0 at least two of R1, R2, R3, R4 and R5 must be hydrogen; (2) the thienyl moiety wherein R, is hydrogen, an alkyl group of up to 3 carbons, fluorine, chlorine or bromine; X is Ch2 0 or S and m is the number 0 or 1, provided that when R0 is a thienyl moiety then m is O; and the tautomers of the above compounds.

  本研究公开了 2-羰基-3-羟基-2-烯腈、其作为抗关节炎剂的用途及其制备工艺。活性化合物具有如下式子 式中 n 是 1 至 3 的整数（含）； M 是氢或药学上可接受的阳离子； R6 是 1 至 4 个碳原子的烷基； R" 是下列芳香基团之一： (1) 其中 R1、R2、R3、R4 和 Ri 相同或不同，并且是 ）氢、卤素、最多 4 个碳原子的烷基、最多 4 个碳原子的烷氧基、三氟甲基或三氯甲基，但当 m 为数字 0 时，R1、R2、R3、R4 和 R5 中至少有两个必须是氢； (2) 噻吩基 其中 R 是氢、最多 3 个碳原子的烷基、氟、氯或溴； X 是 Ch2 0 或 S，m 是数字 0 或 1，但当 R0 是噻吩基时，m 是 O；以及上述化合物的同系物。
• Preiss, A.; Dietzel, St.; Fedgenhaeuer, H., Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 4, p. 569 - 574
  作者：Preiss, A.、Dietzel, St.、Fedgenhaeuer, H.、Hesse, B.

  DOI：——

  日期：——
• An Efficient Diastereoselective Reduction of α-Alkyl-β-keto Carbonitriles with TiCl4/BH3 or LiBH4/CeCl3 to syn- or anti-α-Alkyl-β-hydroxy Carbonitriles
  作者：Renato Dalpozzo、Giuseppe Bartoli、Marcella Bosco、Antonio De Nino、Antonio Procopio、Letizia Sambri、Antonio Tagarelli

  DOI：10.1002/1099-0690(200108)2001:15<2971::aid-ejoc2971>3.0.co;2-k

  日期：2001.8

  alpha -Alkyl-beta -keto carbonitriles can be reduced stereoselectively to syn- and anti-alpha -alkyl-beta -hydroxy carbonitriles. The stereoselectivity can be explained in terms of properties of the Lewis acid employed. TiCl4 in noncoordinating solvents such as dichloromethane, followed by reduction with the borane/pyridine complex, predominantly led to the syrz-alpha -alkyl-beta -hydroxy carbonitriles, according to a chelate transition state, whereas CeCl3 in coordinating solvents such as THF, followed by reduction with LiBH4, predominantly led to the anti-isomers, in agreement with an open-chain transition state. The reduction to syn-alpha -alkyl-beta -hydroxy carbonitriles is the first general preparation of these compounds.