2-chloro-4-(tert-butyldimethylsililoxy)butanal | 669772-02-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-chloro-4-(tert-butyldimethylsililoxy)butanal
• 英文别名: 4-(t-butyldimethylsilyloxy)-2-chlorobutanal；4-[Tert-butyl(dimethyl)silyl]oxy-2-chlorobutanal
• CAS: 669772-02-5
• 化学式: C₁₀H₂₁ClO₂Si
• 分子量: 236.814
• InChiKey: HEGBGNCTMMYRDT-UHFFFAOYSA-N

物化性质

• 沸点：
  245.0±25.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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-chloro-4-(tert-butyldimethylsililoxy)butanal 在 potassium permanganate 、 disodium hydrogenphosphate 、 叔丁醇 作用下， 生成 2-chloro-4-tert-butyldimethylsilyloxybutanoic acid
  参考文献：
  名称：

  醛的直接有机催化不对称α-氯化

  摘要：

  已经开发了醛的直接有机催化对映选择性 α-氯化。使用容易获得的催化剂如 l-脯氨酸酰胺和 (2R,5R)-二苯基吡咯烷，以 NCS 作为氯源，对一系列不同的醛进行反应。α-氯醛的产率高达 99%，ee 高达 95%。通过标准还原将 α-氯醛转化为相应的 α-氯醇（>90% 产率）并进一步转化为末端环氧化物和氨基醇，证明了醛的对映选择性 α-氯化的合成效用在不损失光学纯度的情况下获得。氧化 α-氯醛，然后酯化，得到光学活性的 α-氯酯，而没有损失光学纯度。

  DOI：

  10.1021/ja049231m
• 作为产物：
  描述：

  4-(叔丁基二甲基甲硅烷基)氧代-1-丁醇 在 磺酰氯 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 2-chloro-4-(tert-butyldimethylsililoxy)butanal
  参考文献：
  名称：

  13-Demethyl-13-substituted-13,14-dihydroretinols as potential affinity labels of retinol-binding proteins: syntheses and stability studies

  摘要：

  13-Demethyl-13-substituted-13,14-dihydroretinois were synthesized and their stability under various conditions was measured in order to evaluate whether they would be useful as affinity labels of retinol binding proteins and retinol metabolizing enzymes. The 13-chloro analog could not be isolated because it eliminated HCl under the Wittig reaction conditions of its preparation. The trans- and cis-13,14-epoxy analogs are stable in non-protic organic solvents, but undergo an elimination reaction under various chromatographic conditions and in mixtures of organic solvents with water or alcohol. The 13-hydroxy and 13-methoxy analogs are stable in aqueous solutions and are therefore suitable for biological studies. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.09.002

文献信息

• Direct Organocatalytic Asymmetric α-Chlorination of Aldehydes
  作者：Nis Halland、Alan Braunton、Stephan Bachmann、Mauro Marigo、Karl Anker Jørgensen

  DOI：10.1021/ja049231m

  日期：2004.4.1

  The direct organocatalytic enantioselective α-chlorination of aldehydes has been developed. The reaction proceeds for a series of different aldehydes with NCS as the chlorine source using easily available catalysts such as l-proline amide and (2R,5R)-diphenylpyrrolidine. The α-chloro aldehydes are obtained in up to 99% yield and up to 95% ee. The synthetic utility of the enantioselective α-chlorination

  已经开发了醛的直接有机催化对映选择性 α-氯化。使用容易获得的催化剂如 l-脯氨酸酰胺和 (2R,5R)-二苯基吡咯烷，以 NCS 作为氯源，对一系列不同的醛进行反应。α-氯醛的产率高达 99%，ee 高达 95%。通过标准还原将 α-氯醛转化为相应的 α-氯醇（>90% 产率）并进一步转化为末端环氧化物和氨基醇，证明了醛的对映选择性 α-氯化的合成效用在不损失光学纯度的情况下获得。氧化 α-氯醛，然后酯化，得到光学活性的 α-氯酯，而没有损失光学纯度。
• 13-Demethyl-13-substituted-13,14-dihydroretinols as potential affinity labels of retinol-binding proteins: syntheses and stability studies
  作者：Revital Yefidoff、Limor Weiss、David Avisar、Amnon Albeck

  DOI：10.1016/j.bioorg.2003.09.002

  日期：2004.2

  13-Demethyl-13-substituted-13,14-dihydroretinois were synthesized and their stability under various conditions was measured in order to evaluate whether they would be useful as affinity labels of retinol binding proteins and retinol metabolizing enzymes. The 13-chloro analog could not be isolated because it eliminated HCl under the Wittig reaction conditions of its preparation. The trans- and cis-13,14-epoxy analogs are stable in non-protic organic solvents, but undergo an elimination reaction under various chromatographic conditions and in mixtures of organic solvents with water or alcohol. The 13-hydroxy and 13-methoxy analogs are stable in aqueous solutions and are therefore suitable for biological studies. (C) 2003 Elsevier Inc. All rights reserved.