(+/-)-1-cyano-1,2,3,4-tetrahydronaphthalen-1-yl acetate | 1186319-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-1-cyano-1,2,3,4-tetrahydronaphthalen-1-yl acetate
• 英文别名: 1-cyano-1,2,3,4-tetrahydronaphthalen-1-yl acetate；(1-cyano-3,4-dihydro-2H-naphthalen-1-yl) acetate
• CAS: 1186319-03-8
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: AEFUPAHMJAEYFO-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97 °C
• 沸点：
  355.0±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1-cyano-1,2,3,4-tetrahydronaphthalen-1-yl acetate 在 immobilized Candida antarctica lipase A 、 水 作用下， 以 叔丁基乙醚 为溶剂， 反应 168.0h， 以9%的产率得到3,4-二氢-1(2H)-萘酮
  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：

  3,4-二氢-1(2H)-萘酮 在 盐酸 、 4-二甲氨基吡啶 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 51.0h， 生成 (+/-)-1-cyano-1,2,3,4-tetrahydronaphthalen-1-yl acetate
  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

• One-pot three components synthesis of O-acetylcyanohydrins with TMSCN, acetic anhydride and carbonyl compounds under solvent-free condition
  作者：Santosh T. Kadam、Sung Soo Kim

  DOI：10.1016/j.tet.2009.06.020

  日期：2009.8

  One-pot three components synthesis of O-acetylcyanohydrins has been developed in the presence of B(C6F5)3 as the catalyst. Variety of aldehydes or ketones reacts with TMSCN and acetic anhydride (Ac2O) under the influence of 1 mol % of B(C6F5)3 to give good to excellent yield of the products without solvent at rt.

  在存在B（C 6 F 5）3作为催化剂的情况下，已经开发了O-乙酰基氰醇的一锅三组分合成法。在1摩尔％的B（C 6 F 5）3的影响下，各种醛或酮与TMSCN和乙酸酐（Ac 2 O）反应，从而在室温下在不使用溶剂的情况下获得了良好的优异收率。