3-hydroxy-3-(naphthalen-1-yl)propanenitrile | 1029401-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-hydroxy-3-(naphthalen-1-yl)propanenitrile
• 英文别名: 3-hydroxy-3-naphthalen-1-ylpropanenitrile
• CAS: 1029401-72-6
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: ZGYIXPXUGGEAKA-UHFFFAOYSA-N

物化性质

• 沸点：
  447.0±25.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-(naphthalen-1-yl)propanenitrile 在 盐酸 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (1Z)-3-hydroxy-N'-[(E)-4-methoxybenzylidene]-3-(naphthalen-1-yl)propanehydrazonamide
  参考文献：
  名称：

  Blood Schizontocidal and Gametocytocidal Activity of 3-Hydroxy-N′-arylidenepropanehydrazonamides: A New Class of Antiplasmodial Compounds

  摘要：

  3-Hydroxy N'-arylidenepropanehydrazonamides represent a new class of antiplasmodial compounds. The two most active phenanthrene-based derivatives showed potent in vitro antiplasmodial activity against the 3D7 (sensitive) and Dd2 (multidrug-resistant) strains of plasmodium falciparum with nanomolar IC50 values in the range of 8-28 nM. Further studies revealed that the most promising derivative, bearing a 4-fluorobenzylidene moiety, demonstrated in vivo antiplasmodial activity after oral administration in a P. berghei malaria model, although no complete parasite elimination was achieved with a four dose regimen. The in vivo efficacy correlated well with the plasma concentration levels, and no acute toxicity symptoms (e.9., death or changes in general behaviour or physiological activities) were observed, which is in agreement with a > 1000 fold lower activity agains L6 cells, a primary cell line derived from mammalian (rat) skeletal myoblasts. This indicates that lead compound 29 displays selective activity against P. falciparum. Moreover, both phenanthrene-based derivatives were active against state IV/V gametocytes of p. flaciparum in vitro

  DOI：

  10.1021/jm500811p
• 作为产物：
  描述：

  1-乙烯萘 在 甲醇 、 三甲基氯硅烷 、 三乙胺 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 3-hydroxy-3-(naphthalen-1-yl)propanenitrile
  参考文献：
  名称：

  二氢异恶唑的生物催化不对称开环：从烯烃到β-羟基腈互补对映异构体的无氰化物途径

  摘要：

  通过手性腈的无氰化物合成和醛肟脱水酶催化的坎普消除反应的结合，我们在此报道醛肟脱水酶在5-sub-4,5-二氢异恶唑的不对称开环中合成手性β的新应用-羟基腈，具有广泛的底物范围，出色的对映选择性（高达99％ee）和良好的周转率（高达11 s -1）。简单分离并用碱性试剂处理后，剩余的手性5-sub-4,5-二氢异恶唑可轻松转化为它们相应的β-羟基腈。使用定点诱变，证实了含亚铁血红素的活性位点，并提出了两种可能的去质子化途径。据我们所知，这是第一个用于从一个简单的烯烃一步一步构建手性羟基和腈基的酶促反应，这为合成β-羟基互补对映异构体提供了一种新颖而有用的策略腈。

  DOI：

  10.1039/d0gc01445a

文献信息

• Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine
  作者：Satoru Matsukawa、Eri Kitazaki

  DOI：10.1016/j.tetlet.2008.02.155

  日期：2008.4

  A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.

  高碱性膦三（2,4,6-三甲氧基苯基）膦（TTMPP）使用三甲基甲硅烷基乙腈（TMSCH 2 CN）催化氰基甲基化，从而以羰基化合物和亚胺的高收率得到相应的产物。
• RhI-catalyzed aldol-type reaction of organonitriles under mild conditions
  作者：Akihiro Goto、Kohei Endo、Yu Ukai、Stephan Irle、Susumu Saito

  DOI：10.1039/b800634b

  日期：——

  An aldol-type reaction of organonitriles with aldehydes was catalyzed by a RhI(OR) species under ambient conditions, and the reaction displayed a broad substrate scope with respect to both organonitrile and aldehyde components.

  在环境条件下，RhI（OR）物种催化了有机腈与醛的醛醇型反应，并且该反应对于有机腈和醛组分均显示出较宽的底物范围。
• Synthesis and Reactivity of 4-Aralkoxy(alkoxy)-5,6-dihydro-2H-1,3-oxazine-2-ones
  作者：Thomas Kurz、Mehdi Khankischpur

  DOI：10.1055/s-0029-1217023

  日期：2009.12

  The synthesis of previously unreported 4-aralkoxy(alkoxy)-5,6-dihydro-2H-1,3-oxazine-2-ones, as well as their transformation into various novel 4-functionalized 5,6-dihydro-2H-1,3-oxazine-2-ones and 1,3-oxazinane-2-ones is described.

  本文描述了先前未报告的4-芳烷氧基(烷氧基)-5,6-二氢-2H-1,3-噁唑烷-2-酮的合成，以及它们转化为多种新型4功能化的5,6-二氢-2H-1,3-噁唑烷-2-酮和1,3-噁唑烷-2-酮的过程。
• Stereospecific Oxycyanation of Alkenes with Sulfonyl Cyanide
  作者：Kensuke Kiyokawa、Miu Ishizuka、Satoshi Minakata

  DOI：10.1002/anie.202218743

  日期：2023.3.13

  Intermolecular oxycyanation of alkenes using p-toluenesulfonyl cyanide (TsCN) in the presence of tris(pentafluorophenyl)borane (B(C6F5)3) as a catalyst was shown to be feasible. The developed method offers a simple, scalable, and straightforward approach to access synthetically useful β-hydroxy nitrile derivatives.

  在三（五氟苯基）硼烷（B（C 6 F 5）3 ）作为催化剂存在下，使用对甲苯磺酰氰（TsCN）进行烯烃的分子间氧氰化被证明是可行的。开发的方法提供了一种简单、可扩展且直接的方法来获取合成有用的β-羟基腈衍生物。
• SHIBATA, KATSUYOSHI;KONDO, HIDEHITO;URANO, KATSUYOSHI;MATSUI, MASAKI, CHEM. EXPRESS, 2,(1987) N 3, 169-172
  作者：SHIBATA, KATSUYOSHI、KONDO, HIDEHITO、URANO, KATSUYOSHI、MATSUI, MASAKI

  DOI：——

  日期：——