(甲基二-2-丙烯-1-基硅烷基)-苯 | 2633-60-5

• 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
• 中文名称: (甲基二-2-丙烯-1-基硅烷基)-苯
• 英文名称: diallyl(methyl)(phenyl)silane
• 英文别名: Methyl-diallyl-phenyl-silan；methyl-phenyl-bis(prop-2-enyl)silane
• CAS: 2633-60-5
• 化学式: C₁₃H₁₈Si
• 分子量: 202.371
• InChiKey: HAJJSUOVZDTQET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  (甲基二-2-丙烯-1-基硅烷基)-苯 在 水 、 dibromoborane-methyl sulfide complex 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (Ph)(Me)Si((CH2)3B(OH)2)2
  参考文献：
  名称：

  Hydroxy- and boronic-acid-functionalized carbosilanes: Synthesis and solid state structure of Si(C6H4-4-SiMe2((CH2)3OH))4

  摘要：

  Consecutive synthesis methodologies for the preparation of carbosilanes (Ph)(Me)Si((CH2)(3)B(OH)(2))(2) (2), Si (C6H4-4-SiMe2((CH2)(3)B(OH)(2)))(4) (5), (Ph)(Me)Si((CH2)(3)OH)(2) (3), and Si(C6H4-4-SiMe3-n((CH2)(3)OH)(n))(4) (6a, n = 1; 6b, n = 2; 6c, n = 3) are reported. Boronic acids 2 and 5 are accessible by treatment of (Ph)(Me) Si(CH2CH=CH2)(2) (1) or Si(C6H4-4-SiMe2(CH2CH=CH2))(4) (4a) with HBBr2 center dot SMe2 followed by addition of water, while 3 and 6 are available by the hydroboration of 1 or Si(C6H4-4-SiMe3-n(CH2CH=CH2)(n))(4) (4a, n = 1; 4b, n = 2; 4c, n = 3) with H3B center dot SMe2 and subsequent oxidation with H2O2.The single molecular structure of 6a in the solid state is reported. Representative is that 6a crystallized in the chiral non-centrosymmetric space group P2(1)2(1)2(1) forming 2D layers due to intermolecular hydrogen bond formation of the HO functionalities along the crystallographic a and c axes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.01.006
• 作为产物：
  描述：

  3-溴丙烯 、 甲基苯基二氯硅烷 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以78%的产率得到(甲基二-2-丙烯-1-基硅烷基)-苯
  参考文献：
  名称：

  Zinc mediated allylations of chlorosilanes promoted by ultrasound: Synthesis of novel constrained sila amino acids

  摘要：

  通过锌介导和超声波促进，报道了一种用于氯硅烷的烯基化和丙炔基化的简单、快速和高效方法。作为产生的双烯基硅烷的直接应用，首次制备了三种新颖的约束硅氨基酸。

  DOI：

  10.1039/c4ob00294f

文献信息

• Synthesis of Silacyclohexanones from Divinylsilanes and Allylamines by a Rh-Catalyzed Cyclization
  作者：Jiawei Guo、Song Liu、Qinjiao Pang、Hongyun Zhang、Lu Gao、Li Chen、Zhenlei Song

  DOI：10.1021/acs.orglett.1c04183

  日期：2022.1.21

  An efficient synthesis of silacyclohexanones bearing a variety of silyl substituents has been developed by a [Rh(coe)2Cl]2/PCy3-catalyzed cyclization of divinylsilanes with Jun’s allylamine. The silacyclohexanones can be oxidized with DDQ to give the corresponding silacyclohexadienones, which are further transformed into silicon analog of 2-deoxystreptamine or exo-alkylidenesilacyclohexadienes.

  通过[Rh(coe) 2 Cl] 2 /PCy 3催化的二乙烯基硅烷与Jun's烯丙胺的环化，开发了一种有效合成具有多种甲硅烷基取代基的硅环己酮。硅杂环己酮可以用 DDQ 氧化得到相应的硅环己二烯酮，其进一步转化为 2-脱氧链霉胺或外亚烷基硅环己二烯的硅类似物。
• Controlled introduction of allylic group to chlorosilanes
  作者：Zhifang Li、Xiaojun Cao、Guoqiao Lai、Jinhua Liu、Yong Ni、Jirong Wu、Huayu Qiu

  DOI：10.1016/j.jorganchem.2006.07.023

  日期：2006.11

  controlled manner. Thus allylation of trisubstituted chlorosilanes (R3SiCl) afforded a variety of aryl, aralkyl, and alkenyl substituted allylsilanes. Dichlorosilanes (R2SiCl2) can either afford monoallylated silanes or diallylated silanes depending on the amount of allylsamarium bromide used. Similarly, trichlorosilanes (RSiCl3) can selectively afford mono-, di-, and tri-allylation products. Finally

  用烯丙基溴化mar已经实现了氯硅烷的烯丙基化，特别是以可控的方式。因此，三取代的氯硅烷（R 3 SiCl）的烯丙基化得到各种芳基，芳烷基和烯基取代的烯丙基硅烷。根据所用的烯丙基溴化amount的量，二氯硅烷（R 2 SiCl 2）既可以提供单烯丙基化的硅烷，也可以提供二烯丙基化的硅烷。类似地，三氯硅烷（RSiCl 3）可以选择性提供单，二和三烯丙基化产物。最后，使全氯硅烷（SiCl 4）逐步烯丙基化，并以令人满意的产率获得相应的分别含有一个，两个，三个或四个烯丙基的硅烷。
• Rh-catalyzed 1,4-addition of triallyl(aryl)silanes to α,β-unsaturated carbonyl compounds
  作者：Toshiyuki Kamei、Mizuho Uryu、Toyoshi Shimada

  DOI：10.1016/j.tetlet.2016.03.002

  日期：2016.4

  4-addition of triallyl(aryl)silane to α,β-unsaturated carbonyl compounds was developed. Triallyl(aryl)silanes were used as air- and moisture-stable silicon nucleophiles. Allylsilanes were converted to silanols in situ and underwent transmetalation. This method can accept a wide range of functionalized triallyl(aryl)silane and α,β-unsaturated carbonyl compounds.

  开发了Rh催化的三烯丙基（芳基）硅烷向α，β-不饱和羰基化合物的1,4-加成反应。三烯丙基（芳基）硅烷被用作对空气和水分稳定的硅亲核试剂。将烯丙基硅烷原位转化为硅烷醇并进行金属转移。该方法可以接受各种官能化的三烯丙基（芳基）硅烷和α，β-不饱和羰基化合物。
• Selective mono- and di-allylation and allenylation of chlorosilanes using indium
  作者：Zhifang Li、Chenjun Yang、Hongfang Zheng、Huayu Qiu、Guoqiao Lai

  DOI：10.1016/j.jorganchem.2008.08.028

  日期：2008.12

  Allyl and allenyl groups have been introduced into silicon systems by the allylation and allenylation of chlorosilanes using allyl bromide or propargyl bromide with indium. The allylation of chlorosilanes afforded a variety of aryl, aralkyl, and alkenyl substituted allylsilanes. By applying this method, the reactions of 1-bromo-3-methylbut-2-ene, 3-bromo-2-methylprop-1-ene and 3-bromobut-1-ene with

  通过使用烯丙基溴或炔丙基溴与铟的氯硅烷的烯丙基化和烯丙基化，已将烯丙基和烯丙基引入硅系统。氯硅烷的烯丙基化提供了各种芳基，芳烷基和烯基取代的烯丙基硅烷。通过应用该方法，1-溴-3-甲基丁-2-烯，3-溴-2-甲基丙-1-烯和3-溴丁-1-烯与氯硅烷的反应也可以顺利进行，从而产生区域选择性的烯丙基重排产物丰产。在铟的介导下，二氯硅烷（R 2 SiCl 2）和三氯硅烷（RSiCl 3）可以根据烯丙基溴和铟的用量提供单烯丙基化硅烷或二烯丙基化硅烷。
• Enantioselective Synthesis of Silacyclopentanes
  作者：Kazunobu Igawa、Daisuke Yoshihiro、Yusuke Abe、Katsuhiko Tomooka

  DOI：10.1002/anie.201511728

  日期：2016.5.4

  A variety of functionalized silacyclopentanes were synthesized by highly enantioselective β‐eliminations of silacyclopentene oxides followed by stereospecific transformations. The reaction mechanism of the β‐elimination was elucidated by DFT calculations. An in vitro biological assay with an oxy‐functionalized silacyclopentane showed substantial binding to a serotonin receptor protein.

  通过高度对映选择性的硅杂环戊烯氧化物的β-消除反应，然后进行立体有择的转变，合成了多种功能化的硅杂环戊烷。通过DFT计算阐明了消除β的反应机理。用氧官能化的硅环戊烷进行的体外生物测定显示与血清素受体蛋白具有实质性结合。