Hncguuqcbjwxqv-izzdovswsa- | 90541-60-9

• 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: Hncguuqcbjwxqv-izzdovswsa-
• 英文别名: [(E)-1-ethoxyprop-1-enoxy]-triethylsilane
• CAS: 90541-60-9
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: HNCGUUQCBJWXQV-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Hncguuqcbjwxqv-izzdovswsa- 、 苯乙酮 在 二溴双(2,3,4,5,6-五氟苯基)锡烷 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以87%的产率得到Ethyl 2-methyl-3-phenyl-3-triethylsilyloxybutanoate
  参考文献：
  名称：

  Unusual Preference for Ketone and Reversal of Chemoselectivity in Lewis Acid-Catalyzed Aldol Reaction of Ketene Silyl Acetal

  摘要：

  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.

  DOI：

  10.1021/jo981218v
• 作为产物：
  描述：

  2-溴丙酸乙酯 、 (Et₃Si)₂Hg 以83%的产率得到
  参考文献：
  名称：

  RYBIN, L. I.;GENDIN, D. V.;VYAZANKINA, O. A.;VYAZANKIN, N. S., IZV. AN CCCP. CEP. XIM., 1983, N 7, 1672-1674

  摘要：

  DOI：

文献信息

• Preference of Electron Transfer to Nucleophilic Addition in Reactions of Ketene Silyl Acetals with Quinones and Catalysis of Magnesium Ion
  作者：Morifumi Fujita、Shunichi Fukuzumi、Gen-etsu Matsubayashi、Junzo Otera

  DOI：10.1246/bcsj.69.1107

  日期：1996.4

  β,β-Dimethyl-substituted ketene silyl acetal (1a) reduces p-chloranil and other activated quinones with electron-withdrawing substituents to produce the carbon–oxygen adduct, the hydrolysis of which yields the corresponding hydroquinone ether. The structure of the hydroquinone ether has been determined by the X-ray crystal analysis. The reactions are significantly slowed down in benzene where the charge-transfer

  β,β-二甲基取代的烯酮甲硅烷基缩醛 (1a) 还原对氯苯醌和其他具有吸电子取代基的活化醌，生成碳氧加合物，水解生成相应的氢醌醚。氢醌醚的结构已通过 X 射线晶体分析确定。苯中的反应显着减慢，其中观察到在 1a 和活化的醌之间形成的电子供体 - 受体复合物的电荷转移光谱。观察到的速率常数与从 1a 到 p-氯苯醌的电子转移过程预测的速率常数的比较表明，1a 添加到 p-氯苯醌是通过从 1a 到 p-氯苯醌的电子转移进行的。虽然 1a 和对苯醌之间不发生反应，其电子亲合力明显小于对氯苯醌，在镁离子存在下，对苯醌被 1a 还原是有效的。Mg2...的动力学表达式
• Stereoselective formation of silylketene acetals from esters and trialkylsilyl perchlorates.
  作者：Craig S. Wilcox、Robert E. Babston

  DOI：10.1016/s0040-4039(01)80003-4

  日期：1984.1
• WILCOX, C. S.;BABSTON, R. E., TETRAHEDRON LETT., 1984, 25, N 7, 699-702
  作者：WILCOX, C. S.、BABSTON, R. E.

  DOI：——

  日期：——
• VYAZANKINA, O. A.;GENDIN, D. V.;VYAZANKIN, N. S., TEZ. DOKL. 4 BCEC. KONF. PO METALLOORGAN. XIMII, KAZAN, 13-16 IYUNYA, 198+
  作者：VYAZANKINA, O. A.、GENDIN, D. V.、VYAZANKIN, N. S.

  DOI：——

  日期：——
• 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.