benzaldehyde cyanohydrin (pyranyl ether) | 41865-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: benzaldehyde cyanohydrin (pyranyl ether)
• 英文别名: O-(tetrahydropyran-2-yl)mandelonitrile；phenyl(tetrahydropyranoxy)acetonitrile；2-<(2-tetrahydropyranyl)oxy>-2-phenylacetonitrile；α-(tetrahydropyranyloxy)benzyl cyanide；phenyl(tetrahydro-2H-pyran-2-yloxy)acetonitrile；phenyl[(tetrahydropyran-2-yloxy)]acetonitrile；2-(oxan-2-yloxy)-2-phenylacetonitrile
• CAS: 41865-47-8
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: MVSFLKZTEIXNEN-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzaldehyde cyanohydrin (pyranyl ether) 在 盐酸 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Allylphenylketoncyanhydrin
  参考文献：
  名称：

  Allylic carbonates. Efficient allylating agents of carbonucleophiles in palladium-catalyzed reactions under neutral conditions

  摘要：

  DOI：

  10.1021/jo00209a032
• 作为产物：
  描述：

  sodium hydroxy(phenyl)methanesulfonate 在 盐酸 作用下， 以 水 为溶剂， 生成 benzaldehyde cyanohydrin (pyranyl ether)
  参考文献：
  名称：

  Anderson, John R.; Edwards, Raymond L.; Whalley, Anthony J. S., Journal of the Chemical Society. Perkin transactions I, 1982, p. 215 - 222

  摘要：

  DOI：

文献信息

• Synthesis and muscarinic activities of 1,2,4-thiadiazoles
  作者：Angus M. MacLeod、Raymond Baker、Stephen B. Freedman、Shailendra Patel、Kevin J. Merchant、Michael Roe、John Saunders

  DOI：10.1021/jm00169a041

  日期：1990.7

  synthesized by reaction of the lithium enolate of the 3-methoxycarbonyl compounds followed by ester hydrolysis and decarboxylation. The receptor-binding affinity and efficacy of these compounds as muscarinic ligands was assessed by radioligand binding assays using [3H]-N-methylscopolamine and [3H]oxotremorine-M. Optimal agonist affinity was observed for 3'-methyl compounds. Smaller substituents (H) retained

  制备了一系列在C5带有单或双环胺的新型1,2,4-噻二唑。通过3-甲氧基羰基化合物的烯醇锂反应，然后进行酯水解和脱羧反应，合成了奎尼丁和1-氮杂双环[2.2.1]庚烷衍生物。这些化合物作为毒蕈碱配体的受体结合亲和力和功效通过使用[3H] -N-甲基东pol碱和[3H]氧代短发胺-M的放射性配体结合测定法进行评估。对于3'-甲基化合物观察到最佳激动剂亲和力。较小的取代基（H）保留了较低亲和力的功效，而较大的基团则导致实质上较低的功效。观察到的结合亲和力受围绕C3-C5'键旋转的构象能以及单环或双环胺的空间要求的影响。
• Thiadiazoles useful in the treatment of senile dementia
  申请人：Merck Sharpe & Dohme Ltd.

  公开号：US05405853A1

  公开（公告）日：1995-04-11

  A class of novel thiadiazoles, substituted on one of the ring carbon atoms with a non-aromatic azacyclic or azabicyclic ring system, and substituted on the other ring carbon atom with a substituent of low lipophilicity, or a hydrocarbon substituent; are potent muscarinic agonists, and have good CNS penetrability. The compounds are therefore useful in the treatment of neurological and mental illnesses, and are also of benefit in the treatment of severe painful conditions.

  一类新型噻二唑类化合物，其中一个环上的碳原子被非芳香性氮杂环或氮杂双环系统取代，另一个环上的碳原子被低亲脂性取代基或烃基取代；这些化合物是有效的肌肉收缩素激动剂，并具有良好的中枢神经系统穿透性。因此，这些化合物在治疗神经和精神疾病方面具有用途，并且在治疗严重疼痛症状方面也具有益处。
• Generally Applicable Organocatalytic Tetrahydropyranylation of Hydroxy Functionalities with Very Low Catalyst Loading
  作者：Peter Schreiner、Mike Kotke

  DOI：10.1055/s-2007-965917

  日期：2007.3

  This paper presents the first acid-free, organocatalytic tetrahydropyran and 2-methoxypropene protection of alcohols, phenols, and other ROH derivatives utilizing privileged N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea and a polystyrene-bound analogue. The reactions are broadly applicably (also on preparative scale), in particular, to acid-sensitive substrates such as aldol products, hydroxy esters, acetals, silyl-protected alcohols, and cyanohydrins. The catalytic efficiency is truly remarkably with turnover numbers of 100,000 and turnover frequencies of up to 5700 h-1 at catalyst loadings down to 0.001 mol%. The computationally supported mechanistic interpretation emphasizes the hydrogen bond assisted heterolysis of the alcohol and concomitant preferential stabilization of the oxyanion hole in the transition state.

  本文介绍了首个无酸、有机催化的四氢吡喃和2-甲氧基丙烯对醇、酚及其他ROH衍生物的保护方法，利用了特权的N,N'-双[3,5-双(三氟甲基)苯基]硫脲及其聚苯乙烯结合类似物。这些反应广泛适用于（包括制备规模）对酸敏感的底物，如醛醇产物、羟基酯、缩醛、硅烷保护的醇和氰醇。催化效率非常高，转化数达到10万，转化频率高达每小时5700次，催化剂负载量低至0.001 mol%。通过计算支持的机理解释强调了氢键辅助的醇异裂和过渡态中氧阴离子穴的优先稳定。
• Photoreactivity of .alpha.-fluorinated phenyl alkyl ketones
  作者：Peter J. Wagner、Michael J. Thomas、Allen E. Puchalski

  DOI：10.1021/ja00284a042

  日期：1986.11

  The photoreactivities of the mono-, di-, and tri-..cap alpha..-fluorinated acetophenones have been compared to that of acetophenone itself. All four ketones have similar triplet excitation energies; the three fluorinated ketones have reduction potentials 0.5-0.7 eV lower than that of acetophenone. Triplet reactivity toward alkylbenzenes keeps increasing with fluorine substitution, since the rate-determining

  单-、二-和三-..帽α..-氟化苯乙酮的光反应性已与苯乙酮本身的光反应性进行了比较。所有四种酮都具有相似的三线态激发能；三种氟化酮的还原电位比苯乙酮低0.5-0.7 eV。随着氟取代，对烷基苯的三重反应性不断增加，因为随着酮还原电位的降低，速率决定步骤变为电荷转移络合。一级/三级 CH 对对伞花烃的选择性随着氟的数量增加而增加。对环戊烷的三线态反应性也因氟化而增加，但在两个氟原子处达到峰值，因为最低的三线态从 n,..pi..* 转换为 ..pi..,..pi..* 与两个或三个氟原子和..皮..,..皮.. * 三元组在简单的氢原子提取中是无反应的。相反，戊苯酮的..cap alpha..-氟化不会显着增加三重..gamma..-氢提取的速率。对反应性的诱导效应显然被构象效应所抵消。..cap α..-氟化苯酮主要产生环丁醇而不是 Norrish II 型消除。..cap alpha.
• Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines
  作者：Ichiro Minami、Yukihiro Ohashi、Isao Shimizu、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)94850-0

  日期：——

  Allylation of carbonucleophiles with allylic carbamates under neutral conditions has been studied. The C-allylation of carbonucleophile is competitive with the N-allylation of amines, and the structure of amines is crucial for the selectivity. Bulky secondary amines gave the best results. Also a new method of protection-deprotection of amines as carbamates has been developed. Smooth deprotection is

  已经研究了在中性条件下碳烯亲油与烯丙基氨基甲酸酯的烯丙基化。亲碳亲核体的C-烯丙基化与胺的N-烯丙基化竞争，并且胺的结构对于选择性至关重要。大体积的仲胺效果最好。还开发了一种胺作为氨基甲酸酯的保护-脱保护的新方法。通过氨基甲酸烯丙酯与甲酸的钯催化反应，可以实现平滑的脱保护。该方法特别适用于伯胺，包括旋光氨基酸。