allyl(isopropoxy)dimethylsilane | 98582-95-7

• 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: allyl(isopropoxy)dimethylsilane
• 英文别名: 2-Dimethyl(prop-2-enyl)silyloxypropane；dimethyl-propan-2-yloxy-prop-2-enylsilane
• CAS: 98582-95-7
• 化学式: C₈H₁₈OSi
• 分子量: 158.316
• InChiKey: JJPKGWUPOXGKOY-UHFFFAOYSA-N

物化性质

• 沸点：
  135.2±19.0 °C(Predicted)
• 密度：
  0.798±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  allyl(isopropoxy)dimethylsilane 生成 1,3-二烯丙基四甲基二硅烷
  参考文献：
  名称：

  Brook Michael A., Crowe Grant D., Hiemstra Henk, Can. J. Chem., 72 (1994) N 1, S 264-267

  摘要：

  DOI：
• 作为产物：
  描述：

  二烯丙基二甲基硅烷 在 水 作用下， 生成 allyl(isopropoxy)dimethylsilane
  参考文献：
  名称：

  Brook, Michael A.; Crowe, Grant D.; Hiemstra, Henk, Canadian Journal of Chemistry, 1994, vol. 72, # 1, p. 264 - 268

  摘要：

  DOI：
• 作为试剂：
  描述：

  叔丁基锂 、 苯甲醛 在 allyl(isopropoxy)dimethylsilane 作用下， 以 四氢呋喃 为溶剂， 生成 2,2-二甲基-1-苯基-1-丙醇
  参考文献：
  名称：

  通过烯丙基（异丙氧基）二甲基硅烷一锅三组分合成线性取代的均烯丙基醇。

  摘要：

  [反应：见正文]两步法涉及从烯丙基（异丙氧基）二甲基硅烷（6）合成乙烯基硅烷，然后将所得的乙烯基硅烷进行Pd催化的交叉偶联，从而开发出一种新颖的面向多样性的化合物，三组分合成具有通用结构的1的均芳醇买得起1。

  DOI：

  10.1021/ol048892l

文献信息

• Asymmetric amino-hydroxylation of dienylsilanes. An efficient route to amino-cyclitols
  作者：Rémy Angelaud、Yannick Landais、Kurt Schenk

  DOI：10.1016/s0040-4039(97)00079-8

  日期：1997.2

  Sharpless asymmetric amino-hydroxylation of a silyl-2,5-cyclohexadiene occurs with complete regio- and diastereocontrol. An enantioselectivity of up to 68% e.e. was also observed. An application of the methodology to the synthesis of relevant examples of amino-cyclitols is described.

  甲硅烷基2,5-环己二烯的无尖锐的不对称氨基羟基化反应发生，具有完全的区域和非对映异构控制。还观察到高达68％ee的对映选择性。描述了该方法在氨基-环醇的相关实例的合成中的应用。
• 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.
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.
• The behavior of alkoxides with allyl(chloromethyl)dimethylsilanes and (chloromethyl)dimethylvinylsilane; the abilities of allyl and vinyl groups to migrate from pentacoordinate silicon
  作者：E.A. Sans、H. Shechter

  DOI：10.1016/s0040-4039(00)98411-9

  日期：1985.1
• Tamao, Kohei; Nakajo, Eiji; Ito, Yoshihiko, Synthetic Communications, 1987, vol. 17, # 14, p. 1637 - 1646
  作者：Tamao, Kohei、Nakajo, Eiji、Ito, Yoshihiko

  DOI：——

  日期：——