1-(dimethylphenylsilyl)prop-2-en-1-ol | 719992-93-5

• 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
• 英文名称: 1-(dimethylphenylsilyl)prop-2-en-1-ol
• 英文别名: 1-(dimethylphenylsilyl)-2-propen-1-ol；1-[Dimethyl(phenyl)silyl]prop-2-en-1-ol
• CAS: 719992-93-5
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: KZWYPWCWHQYTQW-UHFFFAOYSA-N

物化性质

• 沸点：
  266.4±33.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(dimethylphenylsilyl)prop-2-en-1-ol 在 tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate 、 copper(II) acetate monohydrate 、 溶剂黄146 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 13.5h， 生成 (Z)-6-(dimethyl(phenyl)silyl)-6-oxo-2-phenyl-N-tosylhex-2-enamide
  参考文献：
  名称：

  Switchable C–H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

  摘要：

  A controllable Rh-catalyzed protocol to access alkylation and akenylation-annulation off N-tosyl acrylamide with, acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp(2) C-H alkylation/alkenylation the instrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or alkylation Products with slight modification of the reaction conditions.

  DOI：

  10.1021/acs.orglett.7b01107
• 作为产物：
  描述：

  苯基二甲基氯硅烷 、 丙烯醛 在 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 1-(dimethylphenylsilyl)prop-2-en-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted γ-Lactams by the [3+2] Annulation of α-Siloxy Allylic Silanes with Chlorosulfonyl Isocyanate

  摘要：

  A stereoselective synthesis of gamma-lactams by the [3+2] annulation of alpha-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted gamma-lactams. Oxidation of the silyl group afforded access to complex beta-hydroxy-gamma-lactams.

  DOI：

  10.1021/ol060596g

文献信息

• Divergent Functionalization of Indoles with Acryloyl Silanes via Rhodium-Catalyzed C–H Activation
  作者：Ping Lu、Chao Feng、Teck-Peng Loh

  DOI：10.1021/acs.orglett.5b01258

  日期：2015.7.2

  by rhodium-catalyzed C–H functionalization of indoles with acryloyl silanes was developed, providing a convenient and highly effective method for the synthesis of functionalized acylsilane derivatives. By tuning the reaction condition, this C–H-activation-initiated reaction proceeds divergently with acryloyl silianes to selectively afford alkylation or alkenylation products via hydroarylation or oxidative

  通过铑催化丙烯腈对吲哚的C–H官能化，开发了一种协议，为合成官能化的酰基硅烷衍生物提供了一种方便而高效的方法。通过调节反应条件，这种由C–H活化引发的反应与丙烯酰基甲硅烷分叉进行，分别通过加氢芳基化或氧化交叉偶联选择性地提供烷基化或烯基化产物。在这两种情况下采用的温和的反应条件均允许宽范围的功能性以及高的反应效率。此外，通过可见光诱导的反应级联，很容易从2-烯基化产物中获得多环吲哚衍生物。
• α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita-Baylis-Hillman Reactions
  作者：Gangababu Marri、Frédéric Justaud、Saibal Das、René Grée

  DOI：10.1002/ejoc.201801343

  日期：2019.1.10

  A short approach toward new acrolein‐type derivatives, functionalized in position 2 is described. It involves, as the key step, a smooth transformation of acylsilanes into aldehydes by irradiation in water‐organic solvent mixtures. The functionalized enals obtained by this new route appear as versatile building blocks for the preparation of natural products and/or bioactive compounds.

  描述了一种新的丙烯醛类衍生物的简短方法，该衍生物在位置2进行了功能化。作为关键步骤，它涉及通过在水-有机溶剂混合物中进行辐照将酰基硅烷平稳地转化为醛。通过这种新途径获得的功能化的烯醛似乎是用于制备天然产物和/或生物活性化合物的通用结构单元。
• Stereoselective Sc(OTf) ₃ ‐Catalyzed Aldol Reactions of Disubstituted Silyl Enol Ethers of Aldehydes with Acetals
  作者：Peter‐Yong Wang、Itai Massad、Ilan Marek

  DOI：10.1002/anie.202101634

  日期：2021.6

  access to stereodefined disubstituted aldehyde-derived silyl enol ethers allowed their successful application in a stereoselective aldol reaction affording the products with excellent yields and diastereomeric ratios. The counter-intuitive stereochemical behavior of this Mukaiyama-aldol reaction is accounted for by a non-classical open transition state.

  易于和模块化获得立体定义的二取代醛衍生的甲硅烷基烯醇醚，使其成功应用于立体选择性羟醛反应中，从而提供了具有优异收率和非对映体比率的产物。此Mukaiyama-aldol反应的违反直觉的立体化学行为是由非经典的开放过渡态引起的。
• Ru-Catalyzed Synthesis of α,β-Unsaturated Acylsilanes and Its Applications in C–N Bond Formation
  作者：Yongli Li、Hao Zhang、Jiawei Li、Dalong Shen、Zhenxing Liu

  DOI：10.1021/acs.orglett.2c04024

  日期：2022.12.16

  α,β-Unsaturated acylsilanes have multifunctional sites and can be used in many transformations. However, the existing methods for preparing them generally suffer from problems, such as low atom and step economy, a narrow substrate scope, etc. Herein, an efficient and general method for accessing α,β-unsaturated acylsilanes through Ru-catalyzed cross-metathesis has been developed. This method is applied

  α,β-不饱和酰基硅烷具有多功能位点，可用于多种转化。然而，现有制备它们的方法普遍存在原子和步骤经济性低、底物范围窄等问题。本文提出了一种通过Ru催化交叉复分解制备α,β-不饱和酰基硅烷的高效通用方法。已经被开发出来。该方法适用于各种酰基硅烷，尤其是经典方法难以制备的β-烷基-α,β-不饱和酰基硅烷。此外，产品的效用已通过两个不同的 C-N 键形成反应得到证明。
• Stereoconvergent [1,2]- and [1,4]-Wittig Rearrangements of 2-Silyl-6-aryl-5,6-dihydropyrans: A Tale of Steric vs Electronic Regiocontrol of Divergent Pathways
  作者：Luis M. Mori-Quiroz、Robert E. Maleczka

  DOI：10.1021/jo5026942

  日期：2015.1.16

  The regiodivergent ring contraction of diastereomeric 2-silyl-5,6-dihydro-6-aryl-(2H)-pyrans via [1,2]- and [1,4]-Wittig rearrangements to the corresponding a-silylcyclopentenols or (alpha-cyclopropyl)acylsilanes favor the [1,4]-pathway by ortho and para directing groups in the aromatic appendage and/or by sterically demanding silyl groups. The [1,2]-pathway is dominant with meta directing or electron-poor aromatic moieties. Exclusive [1,2]-Wittig rearrangements are observed when olefin substituents proximal to the silyl are present. cis and trans diastereomers exhibit different reactivities, but converge to a single [1,2]- or [1,4]-Wittig product with high diastereoselectivity and yield.