crotyltrifluorosilane | 55712-74-8

• 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: crotyltrifluorosilane
• 英文别名: Crotyl-trifluorosilane；but-2-enyl(trifluoro)silane
• CAS: 55712-74-8
• 化学式: C₄H₇F₃Si
• 分子量: 140.18
• InChiKey: CJXYVJHFYSFWFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-3-甲基-2-丁酮 、 crotyltrifluorosilane 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以72%的产率得到2,3,4-Trimethyl-hex-5-ene-2,3-diol
  参考文献：
  名称：

  Chemistry of organosilicon compounds. 260. Allylation of .alpha.-hydroxy ketones with allyltrifluorosilanes and allyltrialkoxysilanes in the presence of triethylamine. Stereochemical regulation involving chelated bicyclic transition states

  摘要：

  DOI：

  10.1021/ja00198a069

文献信息

• Highly Regio- and Stereoselective Allylation of α-Diketones via the Fluorosilicate Route
  作者：Rainer Gewald、Mitsuo Kira、Hideki Sakurai

  DOI：10.1055/s-1996-4151

  日期：1996.1

  Allylation of enolizable α-diketones with allyltrifluorosilanes in the presence of triethylamine gave the corresponding tertiary homoallyl alcohols in good yield in a highly regio- and stereospecific manner. The reaction proceeds as diallylation with allyltrifluorosilanes yielding the 1,2-diols with high diastereoselectivity. The more sterically demanding crotyl- and prenyltrifluorosilanes lead exclusively to monoallylated products with the allyl group being added γ-regioselectively. In addition, highly diastereoselective crotylation was observed in the formation of the monoallylated α-hydroxy ketones. Asymmetric α-diketones were generally allylated at the less enolized ketone group except when both diketone and allylsilane were sterically hindered.

  在三乙胺存在下，使用烯丙基三氟硅烷对可烯醇化的α-二酮进行烯丙基化，得到了相应的三级同烯丙醇，产率良好，并且具有高度的区域选择性和立体选择性。该反应以双烯丙基化进行，使用烯丙基三氟硅烷生成具有高二元选择性的1,2-二醇。更具空间位阻的烯丙基-和预烯丙基三氟硅烷则专门生成单烯丙基化产物，烯丙基团以γ-区域选择性加成。此外，在形成单烯丙基化的α-羟基酮时观察到了高度的二元选择性烯丙基化。当二酮和烯丙基硅烷都受到空间位阻时，通常对不太烯醇化的酮基进行烯丙基化。
• Reactivity Control of an Allylsilane Bearing a 2-(Phenylazo)phenyl Group by Photoswitching of the Coordination Number of Silicon
  作者：Naokazu Kano、Masaki Yamamura、Takayuki Kawashima

  DOI：10.1021/ja037404m

  日期：2004.5.1

  Photoswitching of the coordination number of silicon between four and five in allyldifluoro[2-(phenylazo)phenyl]silane, which was confirmed by X-ray analysis and multinuclear NMR spectroscopy, caused multistep reactions to proceed or stop, yielding tetrafluoro[2-(1-allyl-2-phenylhydrazino)phenyl]silicate without altering other reaction conditions.

  通过 X 射线分析和多核 NMR 光谱证实，烯丙基二氟 [2-(苯基偶氮)苯基]硅烷中硅的配位数在 4 和 5 之间发生光切换，导致多步反应进行或停止，生成四氟 [2-( 1-烯丙基-2-苯基肼基)苯基]硅酸盐而不改变其他反应条件。
• Stereoselective Allylation of<i>β</i>-Hydroxy- and<i>β</i>-Amino-<i>α</i>,<i>β</i>-enones with Allyltrifluorosilane/Triethylamine Systems
  作者：Mitsuo Kira、Kazuhiko Sato、Kazushi Sekimoto、Rainer Gewald、Hideki Sakurai

  DOI：10.1246/cl.1995.281

  日期：1995.4

  Reactions of allyltrifluorosilanes with β-functional-α,β-enones such as o-hydroxy- and o-aminophenyl ketones and 1,3-diketones in the presence of triethylamine yielded the corresponding tertiary homoallyl alcohols in regiospecific and highly diastereoselective manner.

  在三乙胺存在下，烯丙基三氟硅烷与β-官能团-α,β-烯酮（如邻羟基和邻氨基苯基酮以及 1,3-二酮）发生反应，以区域特异性和高非对映选择性的方式生成相应的叔均烯丙基醇。
• Regiospecific and highly stereoselective allylation of aldehydes with allyltrifluorosilane activated by fluoride ions.
  作者：Mitsuo Kira、Mineo Kobayashi、Hideki Sakurai

  DOI：10.1016/s0040-4039(01)83867-3

  日期：1987.1
• Chemistry of organosilicon compounds. 260. Allylation of .alpha.-hydroxy ketones with allyltrifluorosilanes and allyltrialkoxysilanes in the presence of triethylamine. Stereochemical regulation involving chelated bicyclic transition states
  作者：Kazuhiko Sato、Mitsuo Kira、Hideki Sakurai

  DOI：10.1021/ja00198a069

  日期：1989.8