ethyl 2-(1-((tert-butyldimethylsilyl)oxy)cyclohexyl)acetate

• 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: ethyl 2-(1-((tert-butyldimethylsilyl)oxy)cyclohexyl)acetate
• 英文别名: Ethyl 2-[1-[tert-butyl(dimethyl)silyl]oxycyclohexyl]acetate
• 化学式: C₁₆H₃₂O₃Si
• 分子量: 300.514
• InChiKey: ONDJEFIZVSSTGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 、 环己酮 在 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以98%的产率得到ethyl 2-(1-((tert-butyldimethylsilyl)oxy)cyclohexyl)acetate
  参考文献：
  名称：

  碳酸诱导的位阻酮的Mukaiyama Aldol型反应

  摘要：

  1,1,3,3-四（三氟甲磺酰基）丙烷（Tf 2 CHCH 2 CHTf 2）是对位阻酮的Mukaiyama aldol型反应最有效的布朗斯台德酸预催化剂之一。通过使用0.5〜2.0摩尔％的Tf 2 CHCH 2 CHTf 2，α-取代的环己酮与2-甲硅烷基氧呋喃的乙烯基类Mukaiyama aldol反应平稳地进行，从而以优异的收率得到了aldol产物，而没有非对映选择性的损失。在类似条件下，无环烯酮甲硅烷基缩醛也可作为对位阻酮的亲核试剂。这些发现表明，Tf 2 CHCH 2 CHTf 2 诱导的Mukaiyama aldol型反应可以克服反应位点之间的空间位阻。

  DOI：

  10.1021/jo100915e

文献信息

• Cooperative organocatalysis of Mukaiyama-type aldol reactions by thioureas and nitro compounds
  作者：Konstantin V. Bukhryakov、Victor G. Desyatkin、Valentin O. Rodionov

  DOI：10.1039/c6cc01984f

  日期：——

  A unique organocatalytic system for Mukaiyama-type aldol reactions based on the cooperative action of nitro compounds and thioureas has been identified. This system is compatible with a wide range of...

  基于硝基化合物和硫脲的协同作用，已经确定了用于Mukaiyama型羟醛反应的独特有机催化体系。该系统兼容多种...
• Parallel recognition by virtue of differentiation between ketone and aldehyde
  作者：Jian-xie Chen、Junzo Otera

  DOI：10.1016/s0040-4039(98)00039-2

  日期：1998.3

  The concept of parallel recognition has been applied to differentiate between ketone and aldehyde: (C6F5)2SnBr2-catalyzed Mukaiyama-aldol reaction of a mixture of these two carbonyl substrates with a mixture of enol silyl ethers derived from esters and ketones results in exclusive formation of ketone/ester and aldehyde/ketone aldol adducts, respectively.

  平行识别的概念已用于区分酮和醛：（C 6 F 5）2 SnBr 2催化的这两种羰基底物的混合物与衍生自酯和酮的烯醇甲硅烷基醚的混合物的Mukaiyama- aldol反应分别导致酮/酯和醛/酮羟醛加合物的排他性形成。
• Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered Ketones
  作者：Hikaru Yanai、Yasuhiro Yoshino、Arata Takahashi、Takeo Taguchi

  DOI：10.1021/jo100915e

  日期：2010.8.6

  Brønsted acid precatalysts for the Mukaiyama aldol type reactions of sterically hindered ketones. By using Tf2CHCH2CHTf2 in a range from 0.5 to 2.0 mol %, the vinylogous Mukaiyama aldol reaction of α-substituted cyclohexanones with 2-silyloxyfurans smoothly proceeded to give the aldol products in excellent yield without the loss of diastereoselectivity. Under similar conditions, acyclic ketene silyl acetals

  1,1,3,3-四（三氟甲磺酰基）丙烷（Tf 2 CHCH 2 CHTf 2）是对位阻酮的Mukaiyama aldol型反应最有效的布朗斯台德酸预催化剂之一。通过使用0.5〜2.0摩尔％的Tf 2 CHCH 2 CHTf 2，α-取代的环己酮与2-甲硅烷基氧呋喃的乙烯基类Mukaiyama aldol反应平稳地进行，从而以优异的收率得到了aldol产物，而没有非对映选择性的损失。在类似条件下，无环烯酮甲硅烷基缩醛也可作为对位阻酮的亲核试剂。这些发现表明，Tf 2 CHCH 2 CHTf 2 诱导的Mukaiyama aldol型反应可以克服反应位点之间的空间位阻。
• Parallel Differentiated Recognition of Ketones and Acetals
  作者：Jian-xie Chen、Junzo Otera

  DOI：10.1002/(sici)1521-3773(19980202)37:1/2<91::aid-anie91>3.0.co;2-a

  日期：1998.2.2
• Unusual Preference for Ketone and Reversal of Chemoselectivity in Lewis Acid-Catalyzed Aldol Reaction of Ketene Silyl Acetal
  作者：Jian-xie Chen、Katsumasa Sakamoto、Akihiro Orita、Junzo Otera

  DOI：10.1021/jo981218v

  日期：1998.12.1

  Ketene silyl acetals undergo facile reaction with ketones in the presence of a Lewis acid such as (C6F5)(2)SnBr2, TMSOTf, or Sc(OTf)(3). This unique reactivity allows ketones to react in preference to aldehydes or acetals in competitive aldol-type reactions. Upon treatment with keto aldehydes or keto acetals, ketene silyl acetals provide single products derived from the exclusive reaction with the ketonic function. Particularly noteworthy is the discrimination of ketones from aldehydes in naked forms. It has been proved that such bias results from the differentiated recognition of ketone and aldehyde carbonyls. The ternary system consisting of ketene silyl acetal, carbonyl, and an appropriate Lewis acid is crucial for achieving the effective differentiation.