2,2-bis(4-fluorophenyl)acetonitrile | 37742-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-bis(4-fluorophenyl)acetonitrile
• 英文别名: bis(4-fluorophenyl)acetonitrile；4-fluoro-α-(4-fluorophenyl)benzeneacetonitrile
• CAS: 37742-99-7
• 化学式: C₁₄H₉F₂N
• 分子量: 229.229
• InChiKey: JPKIYKWSYBYKIS-UHFFFAOYSA-N

物化性质

• 沸点：
  314.1±32.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-bis(4-fluorophenyl)acetonitrile 在 盐酸 、 3 A molecular sieve 、 氨 、 氢气 、 镍 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0~60.0 ℃ 、6.08 MPa 条件下， 反应 29.0h， 生成 S 9788
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017
• 作为产物：
  描述：

  对溴氟苯 在 indium(III) bromide 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2,2-bis(4-fluorophenyl)acetonitrile
  参考文献：
  名称：

  C（sp2-）-H键的插入中的不同选择性：双金催化竞争实验中的苯甲富烯。

  摘要：

  通过双重金催化，开发了前所未有的，通常几乎定量的三环芳族化合物。这种合成途径通过在容易获得的起始原料中插入C（sp 2）-H键，扩大了苯并富烯衍生物的范围。相对于竞争的芳族CH位置，该插入以排他的化学选择性进行。在选择性确定步骤中具有两个相互竞争的邻-芳基CH键的双向合成也显示出完美的选择性。通过对两种可能的中间体的计算研究可以解释这一结果。两个不等价的芳基CH键与苄基甲基的分子内竞争也显示出完美的选择性。

  DOI：

  10.1002/chem.201801031

文献信息

• I₂-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO₂ incorporating oxyamination of the CC bond
  作者：Sheng Wang、Xiaowei Zhang、Chengyao Cao、Chao Chen、Chanjuan Xi

  DOI：10.1039/c7gc01992k

  日期：——

  oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency

  据报道烯烃与环境CO 2的无金属氧化胺化反应。在存在I 2和DBU的情况下，将CO 2作为保护基团原位施用，以调节氨基的亲核性并促进具有高化学选择性的4-戊烯胺的双环化。此外，该反应提供了一种可行的方法来制备对功能基团具有良好耐受性且在温和条件下具有高效率的脯氨醇氨基甲酸酯。
• Synthesis of α-aryl nitriles through B(C6F5)3-catalyzed direct cyanation of α-aryl alcohols and thiols
  作者：Gurusamy Rajagopal、Sung Soo Kim

  DOI：10.1016/j.tet.2009.03.073

  日期：2009.5

  Various α-aryl nitriles have been prepared in excellent yield from the corresponding α-aryl alcohols employing 3 mol % of B(C6F5)3 (1) as Lewis acid catalyst and (CH3)3SiCN (TMSCN) as cyanide source. Cyano transfer from TMSCN to alcohol proceeds within short reaction time at rt. α-Aryl thiols also produce corresponding nitriles in good to excellent yield at reflux condition.

  使用3 mol％的B（C 6 F 5）3（1）作为路易斯酸催化剂和（CH 3）3 SiCN（TMSCN）作为氰化物，由相应的α-芳基醇以优异的产率制备了各种α-芳基腈。来源。在室温下，在短的反应时间内，从TMSCN转移到乙醇的氰基转移。在回流条件下，α-芳基硫醇还可以产生相应的腈，收率好至极好。
• Palladium(II)‐Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of <i>N</i> ‐Protecting Groups
  作者：Chaohuang Chen、Chuanqi Hou、Pinhong Chen、Guosheng Liu

  DOI：10.1002/cjoc.201900516

  日期：2020.4

  An efficient palladium‐catalyzed regioselective 5‐exo aminotrifluoromethoxylation of alkenes has been established herein, which provides a practical route towards the synthesis of OCF3‐containing pyrrolidines. tert‐Butyloxycarbonyl (Boc) as an amino protecting group plays a significant role in both the chemo‐ and regioselectivities. In addition, preliminary mechanistic studies reveal that the amino

  本文已经建立了一种有效的钯催化烯烃的区域选择性5-外氨基三氟甲氧基化反应，为合成含OCF 3的吡咯烷提供了一条可行的途径。叔丁氧羰基（Boc）作为氨基保护基团在化学和区域选择性中都起着重要作用。此外，初步的机理研究表明，底物的氨基保护基团和钯催化剂的抗衡阴离子在反应效率中起着关键作用，大概是由于烷基-Pd（II）中间体的异构化。此外，还可以通过引入空间庞大的吡啶基-恶唑啉配体来实现不对称的5-exo氨基三氟甲氧基化反应。
• Arylalkylheterocyclic amines,N-substituted by aryloxyalkyl group in a
  申请人：A. H. Robins Company, Incorporated

  公开号：US04950674A1

  公开（公告）日：1990-08-21

  A method of inhibiting Type 1 allergic responses in a living animal body with substituted heterocyclic amines is disclosed wherein the active agents are expressed generally by the formula which includes certain known and certain known compounds: ##STR1## wherein P is zero, one or two; m is one to six inclusive; A is selected from hydrogen, hydroxy or cyano; d is zero or one; Q is --CH--, CH.sub.2 -- or ##STR2## n is zero or one and when Q is --CH-- and n is one, a double bond is formed with one of the adjacent carbons but not both at the same time, and when n and d are zero at the same time, a double bond is formed between the .alpha. carbon and a carbon of the central heterocyclic amine ring; Ar, D and R are selected from phenyl, substituted phenyl, pyridinyl, thienyl, furanyl or naphthyl and in addition, R may have the values benzyl, substituted benzyl, cycloalkyl or loweralkyl and D may additionally have the values: 2H-1-benzopyran-2-one,4-oxo-4H-1-benzopyran-2-carboxylic acid loweralkyl ester, 2,3-dihydro-4H-1-benzopyran-4-one, 1,4-benzodioxanloweralkyl-2-yl or 1,1'-biphenyl-4-yl and the pharmaceutically acceptable salts thereof.

  揭示了一种利用取代杂环胺抑制活体动物体内的1型过敏反应的方法，其中活性剂通常由以下公式表示：其中P为零、一或二；m为一到六（包括六）；A选自氢、羟基或氰基；d为零或一；Q为--CH--、CH.sub.2--或n为零或一，当Q为--CH--且n为一时，与相邻碳之一形成双键，但不同时与两个相邻碳形成双键；当n和d同时为零时，在中心杂环胺环的α碳和一个碳之间形成双键；Ar、D和R选自苯基、取代苯基、吡啶基、噻吩基、呋喃基或萘基，此外，R可能具有苄基、取代苄基、环烷基或较低烷基的值，D还可能具有以下值：2H-1-苯并吡喃-2-酮、4-氧代-4H-1-苯并吡喃-2-羧酸较低烷基酯、2,3-二氢-4H-1-苯并吡喃-4-酮、1,4-苯并二氧杂环较低烷基-2-基或1,1'-联苯基-4-基，以及其药学上可接受的盐。
• N-aryl-piperazinealkanamides useful for protecting hearts from
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04766125A1

  公开（公告）日：1988-08-23

  Novel N-aryl-piperazinealkanamides, having particular substituents attached to one of the carbon atoms of the piperazine ring, which compounds are useful to protect hearts from myocardial injury caused by ischaemia, anoxia or hypoxia.

  新型N-芳基哌嗪烷酰胺，其中特定取代基连接到哌嗪环的一个碳原子上，这些化合物对于保护心脏免受缺血、缺氧或低氧引起的心肌损伤是有用的。