3-[(tert-butyldimethylsilyl)oxy]-2-chloropropanal | 919102-55-9

• 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: 3-[(tert-butyldimethylsilyl)oxy]-2-chloropropanal
• 英文别名: 3-{[tert-Butyl(dimethyl)silyl]oxy}-2-chloropropanal；3-[tert-butyl(dimethyl)silyl]oxy-2-chloropropanal
• CAS: 919102-55-9
• 化学式: C₉H₁₉ClO₂Si
• 分子量: 222.787
• InChiKey: PZRHTYBEGYYHHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  221.1±25.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  3-[(tert-butyldimethylsilyl)oxy]-2-chloropropanal 、 methyl-2-(naphthalen-2-yl)diazene-1-carboxylate 在 bode’s catalyst 、 N,N-二异丙基乙胺 作用下， 以 甲基叔丁基醚 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  串联脱芳构化/重芳构化策略：对映选择性 N-杂环卡宾催化的 α-芳基化†

  摘要：

  在本研究中，描述了卡宾催化的偶氮萘与 α-氯醛的串联脱芳构化/重芳构化反应的第一个例子。该协议能够以优异的对映选择性（高达 99% ee）以良好的收率有效组装手性二氢肉桂酮衍生物。此外，该策略不仅可以实现高度对映选择性的 NHC 催化的亲核芳族取代，还可以形成正式的 Csp 2 -Csp 3键。

  DOI：

  10.1039/c8sc04601h
• 作为产物：
  描述：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 在 N-氯代丁二酰亚胺 、 DL-脯氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 3-[(tert-butyldimethylsilyl)oxy]-2-chloropropanal
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters

  摘要：

  The N-heterocyclic carbene (NHC)-catalyzed trifluoromethylation of alpha-chloro aldehydes was developed, allowing straightforward access to valuable alpha-trifluoromethyl ester derivatives. The unique combination of an electrophilic trifluoromethylation reagent with NHC catalysis was the key for the functionalization of a broad range of alpha-chloro aldehydes, and the products are formed in moderate to good yields. Investigations of the enantioselective version of this reaction afforded the enantioenriched products in moderate yields with good ee values.

  DOI：

  10.1021/acs.orglett.8b01482

文献信息

• Lithium Aldol Reactions of α-Chloroaldehydes Provide Versatile Building Blocks for Natural Product Synthesis
  作者：Robert Britton、Shira Halperin、Baldip Kang

  DOI：10.1055/s-0030-1260032

  日期：2011.6

  The lithium aldol reaction of α-chloroaldehydes provides 1,2-anti-configured β-ketochlorohydrins. The scope of this reaction is demonstrated as well as its application to the synthesis of the C4-C15 segment of haterumalide NA.

  α-氯醛的锂醇缩合反应提供了1,2-反式构型的β-酮氯醇。该反应的范围得到了展示，并介绍了其在合成haterumalide NA的C4-C15片段中的应用.
• ENANTIOSELECTIVE REACTIONS CATALYZED BY CHIRAL TRIAZOLIUM SALTS
  申请人：Bode Jeffrey

  公开号：US20100210452A1

  公开（公告）日：2010-08-19

  This invention provides a convenient method for converting imines and other electrophiles into heterocyclic ring systems. The process does not require the use of metallic reagents, and is catalyzed by an organic heterocyclic carbene catalyst. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. Chiral heterocyclic carbene catalysts of the invention and methods of using these catalysts produce chiral heterocycles in high enantiomeric and diastereomeric excess.

  本发明提供了一种将亚胺和其他亲电试剂转化为杂环环系统的方便方法。该过程不需要使用金属试剂，而是由有机杂环卡宾催化剂催化。因此，它可产生所需化合物而不伴随大量金属废物的产生。本发明的手性杂环卡宾催化剂及其使用方法可产生高对映选择性和立体异构选择性的手性杂环。
• Enantioselective reactions catalyzed by chiral triazolium salts
  申请人：Bode Jeffrey

  公开号：US08501658B2

  公开（公告）日：2013-08-06

  This invention provides a convenient method for converting imines and other electrophiles into heterocyclic ring systems. The process does not require the use of metallic reagents, and is catalyzed by an organic heterocyclic carbene catalyst. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. Chiral heterocyclic carbene catalysts of the invention and methods of using these catalysts produce chiral heterocycles in high enantiomeric and diastereomeric excess.

  本发明提供了一种将亚胺和其他亲电试剂转化为杂环环系统的便捷方法。该过程不需要使用金属试剂，且由有机杂环卡宾催化剂催化。因此，它可以在不产生大量金属废物的情况下产生所需的化合物。本发明的手性杂环卡宾催化剂及使用这些催化剂的方法可以高对映选择性地产生手性杂环化合物。
• N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters
  作者：Fabien Gelat、Atanu Patra、Xavier Pannecoucke、Akkattu T. Biju、Thomas Poisson、Tatiana Besset

  DOI：10.1021/acs.orglett.8b01482

  日期：2018.7.6

  The N-heterocyclic carbene (NHC)-catalyzed trifluoromethylation of alpha-chloro aldehydes was developed, allowing straightforward access to valuable alpha-trifluoromethyl ester derivatives. The unique combination of an electrophilic trifluoromethylation reagent with NHC catalysis was the key for the functionalization of a broad range of alpha-chloro aldehydes, and the products are formed in moderate to good yields. Investigations of the enantioselective version of this reaction afforded the enantioenriched products in moderate yields with good ee values.
• A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation
  作者：Zijun Wu、Jian Wang

  DOI：10.1039/c8sc04601h

  日期：——

  the carbene-catalyzed tandem dearomatization/rearomatization reaction of azonaphthalenes with α-chloroaldehydes is described. This protocol enables the efficient assembly of chiral dihydrocinnolinone derivatives in good yields with excellent enantioselectivities (up to 99% ee). Moreover, this strategy enables not only the highly enantioselective NHC-catalyzed nucleophilic aromatic substitution, but also

  在本研究中，描述了卡宾催化的偶氮萘与 α-氯醛的串联脱芳构化/重芳构化反应的第一个例子。该协议能够以优异的对映选择性（高达 99% ee）以良好的收率有效组装手性二氢肉桂酮衍生物。此外，该策略不仅可以实现高度对映选择性的 NHC 催化的亲核芳族取代，还可以形成正式的 Csp 2 -Csp 3键。