allyl<(-)-menthoxy>dimethylsilane | 123464-08-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: allyl<(-)-menthoxy>dimethylsilane
• 英文别名: dimethyl-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-prop-2-enylsilane
• CAS: 123464-08-4
• 化学式: C₁₅H₃₀OSi
• 分子量: 254.488
• InChiKey: CEKNRPUQTVRQSE-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  壬醛 、 allyl<(-)-menthoxy>dimethylsilane 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以46%的产率得到cis-4-fluoro-2,6-dioctyltetrahydropyran
  参考文献：
  名称：

  Lewis acid-promoted condensation of allylalkoxysilanes with carbonyl compounds. Synthesis of tetrahydropyrans

  摘要：

  DOI：

  10.1021/jo00285a025
• 作为产物：
  描述：

  L-薄荷醇 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 allyl<(-)-menthoxy>dimethylsilane
  参考文献：
  名称：

  Lewis acid-promoted condensation of allylalkoxysilanes with carbonyl compounds. Synthesis of tetrahydropyrans

  摘要：

  DOI：

  10.1021/jo00285a025

文献信息

• Regio- and Stereo-selective Reaction of Chiral Alkoxy- and Aminomethyl-substituted α-Silylallyl Carbanions with Aldehydes
  作者：Li Liu、Dong Wang

  DOI：10.1039/a802886i

  日期：——

  The reactions of chiral alkoxy- and aminomethyl-substituted α-silylallyl carbanions with aldehydes gave 1-silyl-homoallylic alcohols with high γ-regioselection and E-stereoselection, as well as a diastereomeric excess of 8–69%, depending on the chiral substituents on silicon, the aldehydes and the base used.

  手性烷氧基和氨基甲基取代的α-甲硅烷基烯丙基碳负离子与醛的反应产生具有高γ-区域选择性和E-立体选择以及1-（对映体过量）8-69％的1-甲硅烷基-全烯丙基醇，具体取决于手性取代基在硅，醛和碱上使用。
• Asymmetric allylation of aldehydes and glyoxylates through `C-centered' chiral pentacoordinate allylsilicates or promoted by Lewis acid
  作者：Dong Wang、Zhi Gang Wang、Ming Wen Wang、Yong Jun Chen、Li Liu、Yi Zhu

  DOI：10.1016/s0957-4166(99)00004-x

  日期：1999.1

  One-pot asymmetric allylation of aldehydes and glyoxylates with 'C-centered' chiral pentacoordinate allylsilicates generated from a chiral diol-modified allyltrichlorosilane 8 in the presence of Lewis bases, gave optically active homoallylic alcohols 4 with relatively high enantioselectivity (up to 81% ee). The reactions proceed via a six-membered cyclic transition state. In contrast, the allylation reactions of glyoxylate with allylalkoxysilanes promoted by TiCl4 proceed through an acyclic transition state. The chiral auxiliaries residing at different positions on the molecules exhibited different abilities for asymmetric induction, depending on the reaction pathway and the stereochemistry of the transition state. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Lewis acid-promoted condensation of allylalkoxysilanes with carbonyl compounds. Synthesis of tetrahydropyrans
  作者：Z. Y. Wei、D. Wang、J. S. Li、T. H. Chan

  DOI：10.1021/jo00285a025

  日期：1989.11