4-(hydroxymethyl)-2-nitrobenzonitrile | 89939-36-6

• 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: 4-(hydroxymethyl)-2-nitrobenzonitrile
• 英文别名: 3-Nitro-4-cyan-benzylalkohol；α-hydroxy-2-nitro-p-tolunitrile
• CAS: 89939-36-6
• 化学式: C₈H₆N₂O₃
• 分子量: 178.147
• InChiKey: CZAOZHSQQHDAIV-UHFFFAOYSA-N

物化性质

• 熔点：
  78.5-80.5 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  421.2±40.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(hydroxymethyl)-2-nitrobenzonitrile 在 氢氧化钾 作用下， 生成 2-羟基-4-(羟基甲基)苯甲腈
  参考文献：
  名称：

  Banse, Chemische Berichte, 1894, vol. 27, p. 2165

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氰基-3-硝基苯甲酸 在 N-甲基吗啉 、 氯甲酸异丁酯 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.53h， 以2 g的产率得到4-(hydroxymethyl)-2-nitrobenzonitrile
  参考文献：
  名称：

  Improving the Selectivity of PACE4 Inhibitors through Modifications of the P1 Residue

  摘要：

  Paired basic amino acid cleaving enzyme 4 (PACE4), a serine endoprotease of the proprotein convertases family, has been recognized as a promising target for prostate cancer. We previously reported a selective and potent peptide based inhibitor for PACE4, named the multi-Leu peptide (Ac-LLLLRVKR-NH2 sequence), which was then modified into a more potent and stable compound named C23 with the following structure: Ac-DLeu-LLLRVK-Amba (Amba: 4-amidinobenzylamide). Despite improvements in both in vitro and in vivo profiles of C23, its selectivity for PACE4 over furin was significantly reduced. We examined other Argmimetics instead of Amba to regain the lost selectivity. Our results indicated that the replacement of Amba with 5-(aminomethyl)picolinimidamide increased affinity for PACE4 and restored selectivity. Our results also provide a better insight on how structural differences between 51 pockets of PACE4 and furin could be employed in the rational design of selective inhibitors.

  DOI：

  10.1021/acs.jmedchem.8b01381
• 作为试剂：
  描述：

  乙酸烯丙酯 、 (3S,4R)-5-((4-methoxybenzyl)oxy)-4-methylpentane-1,3-diol 在 4-(hydroxymethyl)-2-nitrobenzonitrile 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以87.5%的产率得到
  参考文献：
  名称：

  胞藻霉素C关键中间体的催化不对称合成

  摘要：

  我们完成了sphyphycin C的正式全合成。该合成证明了催化不对称直接硫代酰胺-醛醇缩醛反应在制备聚酮化合物结构中的效用，并且是通过非对映选择性烯丙基化和烯丙基化环化作为其他关键转化而完成的。报告的过程以比先前报告的合成更少的步骤（14个步骤）访问与C7–C18框架相对应的Miyashita的关键片段。

  DOI：

  10.1016/j.tetlet.2015.12.051

文献信息

• Practical and Chemoselective Reduction of Acyl Chloride to Alcohol by Borohydride in Aqueous Dichloromethane
  作者：Ramya Rajan、Sachin Badgujar、Kamaljit Kaur、Yashwardhan Malpani、Pranab R. Kanjilal

  DOI：10.1080/00397910903340645

  日期：2010.8.31

  simple methodology for the reduction of acid chlorides to their corresponding alcohols has been developed. Various carboxylic acids were converted to alcohols in excellent yields using NaBH4-K2CO3 in a mixed solvent system of dichloromethane and water (1:1) in the presence of a phase-transfer catalyst at low temperature. The importance of the work is its simplicity, selectivity, excellent yield, and very

  已开发出一种将酰氯还原为其相应醇的简单方法。在低温相转移催化剂的存在下，在二氯甲烷和水 (1:1) 的混合溶剂体系中，使用 NaBH4-K2CO3 将各种羧酸转化为醇，收率极好。这项工作的重要性在于它的简单性、选择性、出色的收率和非常短的反应时间。这种新的还原条件已被证明是在各种官能团存在下对一系列酰氯的出色化学选择性方法。
• Acetal benzylmaltosides as inhibitors of smooth muscle cell proliferation
  申请人：American Home Products Corporation

  公开号：US06340670B1

  公开（公告）日：2002-01-22

  This invention provides smooth muscle cell proliferation inhibitors of formula I having the structure with the variables defined herein.

  本发明提供了具有本文定义的变量结构的式I平滑肌细胞增殖抑制剂。
• Acylated benzylmaltosides as inhibitors of smooth muscle cell proliferation
  申请人：Mayer C. Scott

  公开号：US20050176652A1

  公开（公告）日：2005-08-11

  This invention provides smooth muscle cell proliferation inhibitors of formula I having the structure wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each, independently, hydrogen, acyl of 2-7 carbon atoms, haloacyl of 2-7 carbon atoms, nitroacyl of 2-7 carbon atoms, cyanoacyl of 2-7 carbon atoms, trifluoromethylacyl of 3-8 carbon atoms, or benzoyl in which the phenyl moiety is substituted with R 8 ; R 6 and R 7 are each, independently, —OH, —OR 9 , O-tert-butyldimethylsilyl, O-trialkylsilyl of 1-6 carbon atoms per alkyl moiety, O-triphenylsilyl, R 8 , R 10 , R 11 , and R 12 are each, independently, hydrogen, —CN, —NO 2 , halogen, CF 3 , alkyl of 1-6 carbon atoms, acetyl, benzoyl, or alkoxy of 1-6 carbon atoms; R 9 is acyl of 2-7 carbon atoms, haloacyl of 2-7 carbon atoms, nitroacyl of 2-7 carbon atoms, cyanoacyl of 2-7 carbon atoms, trifluoromethylacyl of 3-8 carbon atoms, or benzoyl in which the phenyl moiety is substituted with R 8 ; Y is O, S, NH, NMe, or CH 2 ; W is halogen, —CN, CF 3 , alkyl of 1-6 carbon atoms, haloalkyl of 1-6 carbon atoms, nitroalkyl of 1-6 carbon atoms, cyanoalkyl of 1-6 carbon atoms, alkoxyalkyl of 2-12 carbon atoms, alkoxy of 1-6 carbon atoms, or phenyl mono-, di-, or tri-substituted with R 8 ; Z is —NO 2 , —NH 2 , —NHR 13 , or —NHCO-Het; R 13 is acyl of 2-7 carbon atoms, haloacyl of 2-7 carbon atoms, nitroacyl of 2-7 carbon atoms, cyanoacyl of 2-7 carbon atoms, trifluoromethylacyl of 3-8 carbon atoms, benzoyl in which the phenyl moiety is substituted with R 8 , or R 13 is an α-amino acid in which the a carboxyl group forms an amide with the nitrogen of Z, wherein if said amino acid is glutamic acid or aspartic acid, the non-α carboxylic acid is an alkyl ester in which the alkyl moiety contains from 1-6 carbon atoms; Het is pyridyl substituted with R 8 , thienyl substituted with R 8 , furyl substituted with R 8 , oxazolyl substituted with R 8 , pyrazinyl substituted with R 8 , pyrimidinyl substituted with R 8 , or thiazolyl substituted with R 8 ; R 14 is R 8 , —NH 2 , —CO 2 H, or —NH-acyl of 2-7 carbon atoms; n=0-3; with the proviso that when Z is —NHR 13 and Y is O, at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is hydrogen, or at least one of R 6 and R 7 is OH, or a pharmaceutically acceptable salt thereof.

  本发明提供具有结构式I的平滑肌细胞增殖抑制剂，其中R1、R2、R3、R4和R5各自独立地为氢、2-7个碳原子的酰基、2-7个碳原子的卤代酰基、2-7个碳原子的硝基酰基、2-7个碳原子的氰基酰基、3-8个碳原子的三氟甲基酰基或苯甲酰基，其中苯基部分被R8取代；R6和R7各自独立地为-OH、-OR9、O-叔丁基二甲基硅烷基、1-6个碳原子的三烷基硅基或三苯基硅基；R8、R10、R11和R12各自独立地为氢、-CN、-NO2、卤素、CF3、1-6个碳原子的烷基、乙酰基、苯甲酰基或1-6个碳原子的烷氧基；R9为2-7个碳原子的酰基、2-7个碳原子的卤代酰基、2-7个碳原子的硝基酰基、2-7个碳原子的氰基酰基、3-8个碳原子的三氟甲基酰基或苯甲酰基，其中苯基部分被R8取代；Y为O、S、NH、NMe或CH2；W为卤素、-CN、CF3、1-6个碳原子的烷基、1-6个碳原子的卤代烷基、1-6个碳原子的硝基烷基、1-6个碳原子的氰基烷基、2-12个碳原子的烷氧基、1-6个碳原子的烷氧基或苯基单、二或三取代的R8；Z为-NO2、-NH2、-NHR13或-NHCO-Het；R13为2-7个碳原子的酰基、2-7个碳原子的卤代酰基、2-7个碳原子的硝基酰基、2-7个碳原子的氰基酰基、3-8个碳原子的三氟甲基酰基、苯甲酰基，其中苯基部分被R8取代，或者R13是α-氨基酸，其中α-羧基与Z的氮形成酰胺，如果该氨基酸是谷氨酸或天冬氨酸，则非α-羧酸是含有1-6个碳原子的烷基酯；Het是被R8取代的吡啶基、噻吩基、呋喃基、噁唑基、吡嗪基、嘧啶基或噻唑基；R14为R8、-NH2、-CO2H或2-7个碳原子的-NH-酰基；n=0-3；条件是，当Z为-NHR13且Y为O时，R1、R2、R3、R4和R5中至少有一个为氢，或R6和R7中至少有一个为-OH，或其药学上可接受的盐。
• Julia,M.; Chastrette,F., Bulletin de la Societe Chimique de France, 1962, p. 2255 - 2261
  作者：Julia,M.、Chastrette,F.

  DOI：——

  日期：——
• ACYLATED BENZYLMALTOSIDES AS INHIBITORS OF SMOOTH MUSCLE CELL PROLIFERATION
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1133510A2

  公开（公告）日：2001-09-19