R-3-(1,2-dihydroxyethyl)benzonitrile | 212374-06-6

• 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: R-3-(1,2-dihydroxyethyl)benzonitrile
• 英文别名: 3-[(1R)-1,2-dihydroxyethyl]benzonitrile
• CAS: 212374-06-6
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: DTBZIKXQEKAHFC-VIFPVBQESA-N

物化性质

• 沸点：
  361.1±32.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  R-3-(1,2-dihydroxyethyl)benzonitrile 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 R-3-(1,2-dihydroxyethyl)benzamide
  参考文献：
  名称：

  Synthesis of 3-Substituted Benzamides and 5-Substituted Isoquinolin-1(2H)-ones and Preliminary Evaluation as Inhibitors of Poly(ADP-ribose)polymerase (PARP)

  摘要：

  Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. 3-Substituted benzamides and 5-substituted isoquinolin-1-ones have been synthesised and evaluated for inhibition of PARP. Reduction of 3-(bromoacetyl)benzamide, followed by treatment with base, gave RS-3-oxiranylbenzamide. Reduction of 3-(hydroxyacetyl)benzonitrile with bakers' yeast gave 'the R-diol which was converted to R-3-(1,2-dihydroxyethyl)benzamide. Similar reduction of 3-(acetoxyacetyl)benzonitrile led towards the S-diol which was converted to its cyclic acetonide. E-2-(2,6-Dicyanophenyl)-N,N-dimethylethenamine was formed by condensation of 2,6-dicyanotoluene with dimethylformamide dimethyl acetal (DMFDMA); cyclisation under acidic conditions afforded 5-cyanoisoquinolin-1-one. Heck coupling of 5-iodoisoquinolin-1-one with propenoic acid formed E-3-(1-oxoisoquinolin-5-yl)propenoic acid. 3-Oxiranylbenzamide, 5-bromoisoquinolin-1-one and 5-iodoisoquinolin-1-one were among the most potent inhibitors of PARP activity in a preliminary screen in vitro. (C) 1998 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00029-7
• 作为产物：
  描述：

  3-(2-溴乙酰基)苯甲腈 在 baker's yeast 、 potassium acetate 、 三氟乙酸 、 [双(三氟乙酰氧基)碘]苯 、 sodium iodide 、 蔗糖 作用下， 以 水 、 乙腈 为溶剂， 反应 184.0h， 生成 R-3-(1,2-dihydroxyethyl)benzonitrile
  参考文献：
  名称：

  Synthesis of 3-Substituted Benzamides and 5-Substituted Isoquinolin-1(2H)-ones and Preliminary Evaluation as Inhibitors of Poly(ADP-ribose)polymerase (PARP)

  摘要：

  Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. 3-Substituted benzamides and 5-substituted isoquinolin-1-ones have been synthesised and evaluated for inhibition of PARP. Reduction of 3-(bromoacetyl)benzamide, followed by treatment with base, gave RS-3-oxiranylbenzamide. Reduction of 3-(hydroxyacetyl)benzonitrile with bakers' yeast gave 'the R-diol which was converted to R-3-(1,2-dihydroxyethyl)benzamide. Similar reduction of 3-(acetoxyacetyl)benzonitrile led towards the S-diol which was converted to its cyclic acetonide. E-2-(2,6-Dicyanophenyl)-N,N-dimethylethenamine was formed by condensation of 2,6-dicyanotoluene with dimethylformamide dimethyl acetal (DMFDMA); cyclisation under acidic conditions afforded 5-cyanoisoquinolin-1-one. Heck coupling of 5-iodoisoquinolin-1-one with propenoic acid formed E-3-(1-oxoisoquinolin-5-yl)propenoic acid. 3-Oxiranylbenzamide, 5-bromoisoquinolin-1-one and 5-iodoisoquinolin-1-one were among the most potent inhibitors of PARP activity in a preliminary screen in vitro. (C) 1998 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00029-7

文献信息

• Reprogramming Epoxide Hydrolase to Improve Enantioconvergence in Hydrolysis of Styrene Oxide Scaffolds
  作者：Fu‐Long Li、Yan‐Yan Qiu、Yu‐Cong Zheng、Fei‐Fei Chen、Xu–Dong Kong、Jian‐He Xu、Hui‐Lei Yu

  DOI：10.1002/adsc.202000898

  日期：2020.11.4

  Enantioconvergent hydrolysis by epoxide hydrolase is a promising method for the synthesis of important vicinal diols. However, the poor regioselectivity of the naturally occurring enzymes results in low enantioconvergence in the enzymatic hydrolysis of styrene oxides. Herein, modulated residue No. 263 was redesigned based on structural information and a smart variant library was constructed by site‐directed

  通过环氧水解酶的对映体收敛水解是一种重要的邻位二醇合成的有前途的方法。但是，天然酶的区域选择性差会导致苯乙烯氧化物的酶促水解中对映体收敛性低。在此，根据结构信息重新设计了263号残基，并使用“优化的氨基酸字母”通过定点修饰构建了一个智能变体文库，以提高来自Vigna radiata（Vr EH2）的环氧水解酶的区域选择性。M263Q变体对间位异构体R异构体的区域选择性系数（r）与野生型相比，预取代的苯乙烯氧化物提高了40-63倍，变体M263V对对位取代的苯乙烯氧化物的R异构体也表现出更高的区域选择性，从而提高了苯乙烯氧化物支架水解中的对映体收敛性。结构上的洞察力表明263号残基在通过改变结合环境来调节底物结合构象中的关键作用。此外，亲核残基Asp101和环氧化物的两个碳原子之间的攻击距离差异增加，为区域选择性的提高提供了证据。几种易于合成的高价值邻位二醇（> 88％收率，90％–98％
• Aminoalcohol derivatives
  申请人：——

  公开号：US20040138462A1

  公开（公告）日：2004-07-15

  The present invention relates to a compound formula wherein R 1 is phenyl, pyridyl, etc., each of which may be substituted with one or two substituent(s); R 2 is hydrogen, an amino protective group, etc.; R 3 and R 4 are each independently hydrogen, lower alkyl or hydroxy(lower)alkyl; R 5 is aryl, ar(lower)alkyl, etc., each of which may be substituted with one, two or three substituent(s); R 8 is hydrogen or halogen, X is a single bond or O—CH 2 —, and n is 0, 1 or 2, or a salt thereof. The compound [I] of the present invention and pharmaceutically acceptable salts thereof are useful for the prophylactic and/or the therapeutic treatment of pollakiurea or urinary incontinence. 1

  本发明涉及一种化合物配方，其中R1是苯基，吡啶基等，每个基团可以用一个或两个取代基取代；R2是氢，氨基保护基等；R3和R4各自独立地是氢，低碳基或羟基（低）碳基；R5是芳基，芳（低）碳基等，每个基团可以用一个、两个或三个取代基取代；R8是氢或卤素，X是单键或O-CH2-，n为0、1或2，或其盐。本发明的化合物[I]及其药学上可接受的盐对预防和/或治疗多尿或尿失禁非常有用。