2-(benzyloxy)-2-cyclohexylacetaldehyde | 89869-02-3

• 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: 2-(benzyloxy)-2-cyclohexylacetaldehyde
• 英文别名: (benzyloxy)cyclohexylacetaldehyde；2-Cyclohexyl-2-phenylmethoxyacetaldehyde
• CAS: 89869-02-3
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: AKHOMAUEAISMTN-UHFFFAOYSA-N

物化性质

• 沸点：
  328.3±17.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)-2-cyclohexylacetaldehyde 在 indium 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 (4S,5R)-5-(Benzyloxy-cyclohexyl-methyl)-4-methyl-3-methylene-dihydro-furan-2-one
  参考文献：
  名称：

  Experimental Test of Setting Three Contiguous Stereogenic Centers in Water. Diastereoselective Coupling of Geometrically Biased Allylic Bromides to α-Oxy Aldehydes with Indium

  摘要：

  Indium-promoted additions of (Z)-2-(bromomethyl)-2-butenoate to several alpha-(tert-butyldimethylsiloxy) and alpha-(benzyloxy) aldehydes in water have been examined in order to assess the direction and sense of asymmetric induction in these coupling reactions. High levels of the 3,4-syn;4,5-anti diastereomers were produced, reflecting the promising synthetic potential of this chemistry. This stereodifferentiation has been attributed to the strong geometric bias exercised by this allylindium reagent and adherence to a Felkin-Ahn transition-state alignment. Support for this interpretation was gained by comparing the fate of (E)-cinnamyl bromide under comparable circumstances. In this case, the 3,4-anti;4,5-anti diastereomer predominated as expected.

  DOI：

  10.1021/jo970267p
• 作为产物：
  描述：

  3-Benzyloxy-3-cyclohexylprop-1-ene 在 二甲基硫 、 氧气 、 臭氧 作用下， 生成 2-(benzyloxy)-2-cyclohexylacetaldehyde
  参考文献：
  名称：

  Davis, Anthony P.; Jaspars, Marcel, Journal of the Chemical Society. Perkin transactions I, 1992, # 16, p. 2111 - 2118

  摘要：

  DOI：

文献信息

• Aniline mediated oxidative C–C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(d)-amino acid derivatives
  作者：Bin Hu、Yunfeng Li、Zhongjun Li、Xiangbao Meng

  DOI：10.1039/c3ob40685g

  日期：——

  4-methyl aniline mediated method for the oxidative C–C bond cleavage has been developed. The reaction proceeds in air using molecular oxygen as the oxidant, affording one-carbon shortened esters in moderate to good yields within a short time. Moreover, it provides a model reaction for the highly enantioselective synthesis of (D)-serine esters by combining with a L-proline catalyzed Mannich reaction.

  无金属和 4-甲基苯胺已经开发了介导的氧化碳-碳键裂解的方法。该反应使用分子氧作为氧化剂在空气中进行，在短时间内以中等至良好的收率提供了一个碳短的酯。而且，它通过与L-脯氨酸催化的曼尼希反应结合，为（D）-丝氨酸酯的高度对映选择性合成提供了模型反应。
• Diastereoselective Synthesis of α-Oxyaminesvia Gold-, Silver- and Copper-Catalyzed, Three-Component Couplings of α-Oxyaldehydes, Alkynes, and Amines in Water
  作者：Baosheng Huang、Xiaoquan Yao、Chao-Jun Li

  DOI：10.1002/adsc.200606118

  日期：2006.8

  The three-component couplings of α-oxyaldehydes, alkynes, and amines in water were investigated by using gold, silver and copper catalysts. Gold(I) was found to be the most effective catalyst in this reaction to afford propargylamines in good yields and moderate diastereoselectivities. On the other hand, silver catalysts show the best catalytic activities on non-coordinating α-alkyl-substituted aldehydes

  通过使用金，银和铜催化剂研究了水中的α-氧化醛，炔烃和胺的三组分偶联。发现金（I）是该反应中以高收率和中等非对映选择性提供炔丙基胺的最有效催化剂。另一方面，银催化剂对非配位的α-烷基取代的醛显示出最佳的催化活性。
• A protective strategy in carbene complex chemistry. Synthesis of functionalized Fischer carbene complexes via dianion formation
  作者：Satoshi Aoki、Tsutomu Fujimura、Eiichi Nakamura

  DOI：10.1021/ja00034a034

  日期：1992.4

  Anionic derivatives of Fischer-type carbene complexes (A and B) are stable toward strong bases and nucleophiles, and their organic moieties R and R 2 can be elaborated under strongly basic conditions to provide access to heteroaromatic and aliphatic carbene complexes bearing organic functional groups. The concept of anionic protection has been illustrated by the reactions of dianions 9 and 14 and the

  Fischer 型卡宾配合物（A 和 B）的阴离子衍生物对强碱和亲核试剂稳定，它们的有机部分 R 和 R 2 可以在强碱性条件下进行加工，以提供带有有机官能团的杂芳族和脂肪族卡宾配合物。阴离子保护的概念已通过二价阴离子 9 和 14 的反应以及具有多达四个手性中心的卡宾配合物的制备得到说明。还描述了一些实现芳族卡宾配合物邻位锂化的尝试
• Indium-catalyzed Barbier allylation reaction
  作者：Jacques Augé、Nadège Lubin-Germain、Sylvain Marque、Latifa Seghrouchni

  DOI：10.1016/s0022-328x(03)00515-1

  日期：2003.8

  bromide was investigated using a catalytic amount of indium (0), indium (I) or indium (III) salts in the presence of a reducer and chlorotrimethylsilane (TMSCl). The Mn/TMSCl couple turned out to be the most efficient system to regenerate active indium in the allylation reaction of various carbonyl compounds including α- and β-oxygenated aldehydes.

  在还原剂和三甲基氯硅烷（TMSCl）存在下，使用催化量的铟（0），铟（I）或铟（III）盐研究了羰基化合物与烯丙基溴的Barbier烯丙基化反应。事实证明，Mn / TMSCl对是在各种羰基化合物（包括α-和β-氧化醛）的烯丙基化反应中再生活性铟的最有效系统。
• Chelation controlled diastereofacial selectivity in crotyltri--butylstannane additions to α-alkoxyaldehydes
  作者：Gary E. Keck、Eugene P. Boden

  DOI：10.1016/s0040-4039(01)90065-6

  日期：1984.1

  Lewis acid mediated additions of crotyltri-n-butylstannane to chiral α-alkoxyaldehydes generally show excellent (⩾99:1) diastereofacial selectivity; proper choice of lewis acid is crucial for controlling erythro/threo selectivity in the bond formation.

  路易斯酸介导的巴豆基三正丁基锡烷向手性α-烷氧基醛中的加成通常表现出极好的（⩾99：1）非对映选择性。正确选择路易斯酸对于控制键形成中的赤/苏选择性至关重要。