(+/-)-1-hydroxy-1,2,3,4-tetrahydronaphthalene carbonitrile | 76311-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-1-hydroxy-1,2,3,4-tetrahydronaphthalene carbonitrile
• 英文别名: 1-hydroxy-1,2,3,4-tetrahydro-[1]naphthonitrile；1-Hydroxy-1,2,3,4-tetrahydro-[1]naphthonitril；α-Tetralon-cyanhydrin；1-cyano-1-hydroxy-1,2,3,4-tetrahydronaphthalene；1-hydroxy-3,4-dihydro-2H-naphthalene-1-carbonitrile
• CAS: 76311-47-2
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: JGMIPIYDFBVXEV-UHFFFAOYSA-N

物化性质

• 沸点：
  365.1±37.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  甲氧基乙酰氯 、 (+/-)-1-hydroxy-1,2,3,4-tetrahydronaphthalene carbonitrile 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (+/-)-1-cyano-1,2,3,4-tetrahydronaphthalen-1-yl methoxyacetate
  参考文献：
  名称：

  Lipase catalyzed resolution of the quaternary stereogenic center in ketone-derived benzo-fused cyclic cyanohydrins

  摘要：

  The enantioselective preparation of both enantiomers of the benzo-fused cyanohydrin derived from alpha-tetralone via lipase catalyzed processes is described. The (S)-enantiomer has been obtained as the remaining substrate in the CAL-A catalyzed aminolysis of the methoxyacetylated derivative, using a structurally related amine as the nucleophile. The (R)-enantiomer has been obtained as the product of CAL-A or PSL-C catalyzed hydrolysis of the methoxyacetylated derivative in organic solvents. The resolutions of several structural analogs of this cyanohydrin have been also tested under similar conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.004
• 作为产物：
  描述：

  1-(trimethylsilyloxy)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile 在 盐酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 (+/-)-1-hydroxy-1,2,3,4-tetrahydronaphthalene carbonitrile
  参考文献：
  名称：

  Lipase catalyzed resolution of the quaternary stereogenic center in ketone-derived benzo-fused cyclic cyanohydrins

  摘要：

  The enantioselective preparation of both enantiomers of the benzo-fused cyanohydrin derived from alpha-tetralone via lipase catalyzed processes is described. The (S)-enantiomer has been obtained as the remaining substrate in the CAL-A catalyzed aminolysis of the methoxyacetylated derivative, using a structurally related amine as the nucleophile. The (R)-enantiomer has been obtained as the product of CAL-A or PSL-C catalyzed hydrolysis of the methoxyacetylated derivative in organic solvents. The resolutions of several structural analogs of this cyanohydrin have been also tested under similar conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.004

文献信息

• Cu(OTf)2 catalyzed trimethylsilyl cyanide addition to carbonyl compounds
  作者：P. Saravanan、R.Vijaya Anand、Vinod K. Singh

  DOI：10.1016/s0040-4039(98)00594-2

  日期：1998.5

  Copper (II) triflate was found to catalyze Trimethylsilyl cyanide addition to a variety of ketones and aldehydes at rt in an efficient manner.

  发现在室温下，三氟甲磺酸铜（II）可以有效地催化三甲基甲硅烷基氰化物加成到各种酮和醛中。
• Study of the Reaction Between Cyanohydrins and Chlorosulfonyl Isocyanate. A New, Efficient Method for the One-Pot Synthesis of 2,4-Oxazolidinediones
  作者：M. Victoria García、J. Carlos Menéndez、Mercedes Villacampa、Mónica M. Söllhuber

  DOI：10.1055/s-1991-26548

  日期：——

  The reaction between cyanohydrins and chlorosulfonyl isocyanate, followed by acid hydrolysis, provides and efficient route for the one-pot preparation of 5,5-disubstituted 2,4-oxazolidinediones.

  氰基卤素与氯磺酰异氰酸酯发生反应，然后进行酸水解，为一次过制备 5,5 二甲基 2,4-oxazolidinediones 提供了有效的途径。
• Absolute Configuration of Ketone Cyanohydrins by ¹H NMR: The Special Case of Polar Substituted Tertiary Alcohols
  作者：Iria Louzao、Rosa García、José Manuel Seco、Ricardo Riguera

  DOI：10.1021/ol8023314

  日期：2009.1.1

  The absolute configuration of ketone cyanohydrins can be assigned from analysis of the 1H NMR spectra of the corresponding (R)- and (S)-MPA ester derivatives and use of ΔδRS signs. This is an application of the NMR methodology for stereochemical assignment to tertiary alcohols possessing polar groups as substituents.

  酮氰醇的绝对构型可以从分析被分配1个相应的（的1 H NMR谱- [R和（ - ）小号）-MPA酯衍生物和使用Δδ RS迹象。这是NMR方法在立体化学上分配给具有极性基团作为取代基的叔醇的应用。
• Novel spiro-oxazolidinediones
  申请人：Pfizer Inc.

  公开号：US04226875A1

  公开（公告）日：1980-10-07

  Novel spiro-oxazolidinediones useful as aldose reductase inhibitors and as therapeutic agents for the treatment of chronic diabetic complications are disclosed. Pharmaceutical compositions containing the novel compounds and a method of treating chronic diabetic complications are also disclosed.

  本发明公开了一种新型的螺环氧噻唑啉二酮，可用作醛糖还原酶抑制剂和治疗慢性糖尿病并发症的治疗剂。还公开了含有这种新型化合物的药物组合物以及治疗慢性糖尿病并发症的方法。
• Lapworth; Manske, Journal of the Chemical Society, 1928, p. 2546
  作者：Lapworth、Manske

  DOI：——

  日期：——