1,1-Diethoxy-3-trimethylsilanyl-2-trimethylsilanylmethyl-propan-2-ol | 187995-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-Diethoxy-3-trimethylsilanyl-2-trimethylsilanylmethyl-propan-2-ol
• 英文别名: 1,1-Diethoxy-3-trimethylsilyl-2-(trimethylsilylmethyl)propan-2-ol
• CAS: 187995-42-2
• 化学式: C₁₄H₃₄O₃Si₂
• 分子量: 306.593
• InChiKey: WPAVUYHWDYSYIY-UHFFFAOYSA-N

物化性质

• 沸点：
  342.2±37.0 °C(Predicted)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-Diethoxy-3-trimethylsilanyl-2-trimethylsilanylmethyl-propan-2-ol 在 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 (1S,2S,5S)-2-Ethoxy-3-methylene-8-oxa-bicyclo[3.2.1]oct-6-ene
  参考文献：
  名称：

  Vinyl Oxocarbenium Ions in Intermolecular [4 + 3] Cycloaddition Reactions

  摘要：

  DOI：

  10.1021/jo962374+
• 作为产物：
  描述：

  (三甲基硅基)甲基氯化镁 、 2,2-二乙氧基乙酸乙酯 在 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到1,1-Diethoxy-3-trimethylsilanyl-2-trimethylsilanylmethyl-propan-2-ol
  参考文献：
  名称：

  [4+3] Cycloadditions of some allylic dioxolanes

  摘要：

  Four allylic dioxolanes were prepared and reacted with several dienes in the presence of Lewis acids, affording [4+3] cycloadducts. The reaction could be conducted with catalytic amounts of Lewis acid. The use of a chiral Lewis acid gave a cycloadduct with only a low enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.036

文献信息

• Heteroatom-stabilized allylic cations in 4+3 cycloadditions. A tandem Peterson olefination/4+3 cycloaddition reaction
  作者：Michael Harmata、Darin E. Jones

  DOI：10.1016/s0040-4039(97)00775-2

  日期：1997.6

  The readily available tertiary alcohols 4a-c react with selected dienes in the presence of titanium tetrachloride to give 4+3 cycloaddition products. The process is best rationalized as a Peterson olefination followed by allylic cation formation and 4+3 cycloaddition. (C) 1997 Elsevier Science Ltd.
• Chiral cations in 4+3 cycloadditions
  作者：Michael Harmata、Darin E. Jones、Mehmet Kahraman、Uday Sharma、Charles L. Barnes

  DOI：10.1016/s0040-4039(99)00080-5

  日期：1999.3

  The reaction of the chiral acetal 4 with furan and cyclopentadiene in the presence of a Lewis acid gives 4+3 cycloadducts in very good yields. Diastereoselectivity in the case of furan is exceptionally high, while that for the reaction with cyclopentadiene is lower. The sense of diastereoselection in the case of furan is opposite to that which would be predicted on the basis of mechanistic models for the origin of stereoselectivity in many reactions of chiral acetals mediated by Lewis acids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Vinyl Oxocarbenium Ions in Intermolecular [4 + 3] Cycloaddition Reactions
  作者：Michael Harmata、Darin E. Jones

  DOI：10.1021/jo962374+

  日期：1997.3.1
• [4+3] Cycloadditions of some allylic dioxolanes
  作者：Michael Harmata、James A. Brackley、Charles L. Barnes

  DOI：10.1016/j.tetlet.2006.09.036

  日期：2006.11

  Four allylic dioxolanes were prepared and reacted with several dienes in the presence of Lewis acids, affording [4+3] cycloadducts. The reaction could be conducted with catalytic amounts of Lewis acid. The use of a chiral Lewis acid gave a cycloadduct with only a low enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.