(R,E)-1-methyl-4-(prop-1-en-1-ylsulfinyl)benzene | 156767-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,E)-1-methyl-4-(prop-1-en-1-ylsulfinyl)benzene
• 英文别名: (R)-(E)-1-propenyl p-tolylsulfoxide；(E)-1-(p-tolylsulfinyl)-1-propene；1-methyl-4-[(R)-[(E)-prop-1-enyl]sulfinyl]benzene
• CAS: 156767-62-3
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: YSASRYWCORFSIM-STWLFGJUSA-N

物化性质

• 沸点：
  340.9±21.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,E)-1-methyl-4-(prop-1-en-1-ylsulfinyl)benzene 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 Methanesulfonic acid (E)-(R)-1-ethyl-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester
  参考文献：
  名称：

  通过无环烯丙基甲磺酸酯的S（N）2'置换形成对映选择性碳-碳键（1）。

  摘要：

  对映体纯的烯丙基甲磺酰氧基乙烯基亚砜的铜介导的S（N）2'置换以高收率和立体选择性发生。在这些加合物中，新产生的手性中心与乙烯基亚砜官能团相邻，后者应允许随后的手性转移操作。另外，对映体纯的烯基砜和带有烯丙基立体中心的烯烃很容易从这些加合物中以高度几何控制的方式获得。已经研究了结构相关的甲氧基氧化硫和砜与有机铜酸盐的S（N）2'置换。从烯丙基醇位置的单一对映异构体，可以通过调节硫的氧化水平来控制新手性中心的绝对构型。

  DOI：

  10.1021/jo961292i
• 作为产物：
  描述：

  4-甲基苯基亚硫酰氯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (R,E)-1-methyl-4-(prop-1-en-1-ylsulfinyl)benzene
  参考文献：
  名称：

  Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam

  摘要：

  Bornane-10,2-sultam 1 is stereoselectively converted by DMAP-assisted sulfinylation to diastereomerically pure (2R)-N-[(R)-p-tolylsulfinyl]-bornane-10,2-sultam 2 in 77% yield. The crystalline sulfinylating agent 2 reacts with a variety of nucleophiles to afford sulfoxides 3 and sulfinimines 5 in excellent yields and enantioselectivities. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00472-3

文献信息

• Synthesis of Cyclopentenones with C4-Quaternary Stereocenters via Stereospecific [3,3]-Sigmatropic Rearrangement and Applications in Total Synthesis of Sesquiterpenoids
  作者：Weiping Zhou、Arnaud Voituriez

  DOI：10.1021/jacs.1c07966

  日期：2021.10.27

  A cationic gold(I)-catalyzed asymmetric [3,3]-sigmatropic rearrangement of sulfonium leads after cyclization to cyclopentenones with a C4-quaternary stereocenter. Starting with simple vinyl sulfoxides and propargyl silane, numerous compounds were isolated with moderate to good yields and excellent enantiomeric excesses (26 examples). The application of this simple methodology allowed the efficient

  锍的阳离子金 (I) 催化不对称 [3,3]-σ 重排在环化后生成具有 C4-季立体中心的环戊烯酮。从简单的乙烯基亚砜和炔丙基硅烷开始，以中等至良好的收率和优异的对映异构体过量分离了许多化合物（26 个实例）。应用这种简单的方法可以有效地合成五种天然倍半萜类化合物，包括 enokipodin A 和 B、hitoyopodin A、lagopodin A 和 isocuparene-3,4-diol。
• A formal and enantioselective synthesis of (−)-serricornin, the sex pheromone of the cigarette beetle (lasioderma serricorne F.)
  作者：J. Tércio、B. Ferreira、Jacqueline A. Marques、J.P. Marino

  DOI：10.1016/0957-4166(94)80026-x

  日期：1994.4
• Highly Stereocontrolled Formal Synthesis of Brassinolide via Chiral Sulfoxide-Directed S_N2‘ Reactions
  作者：Joseph P. Marino、Alfonso de Dios、Laura J. Anna、Roberto Fernández de la Pradilla

  DOI：10.1021/jo951264k

  日期：1996.1.1

  An efficient stereocontrolled methodology for the preparation of the four contiguous chiral centers of the brassinosteroid side chain is described. Allylic mesyloxy sulfinyl steroids have been found to undergo highly stereoselective S(N)2' displacements when treated with cyanocuprates that provide the required acyclic stereocontrol in the key C-24 position of the steroidal side chain. Preparation of a direct precursor of brassinolide]I, as well as a precursor of naturally occurring (24R)-epibrassinolide, (+)-18, is carried out in two additional steps utilizing asymmetric dihydroxylations of(22E)-olefins (+)-2 and (+)-17. In this manner, a formal synthesis of this plant growth promoter has been completed, and the extension of the scope of this methodology has been explored providing a straightforward route to this family of steroids. Alternative routes to the key olefin (+)-2 are also outlined. Improved selectivity in the addition to aldehyde 7 for the preparation of the Cram (22R)-allylic hydroxy sulfoxides is achieved by controlling the chirality at sulfur or by a condensation-symmetric oxidation sequence employing the analogous vinyl sulfide reagent 22.
• Asymmetric carbon-carbon bond formation via sulfoxide-directed SN2' displacements of acyclic allylic mesylates
  作者：J. P. Marino、A. Viso、Roberto Fernandez de la Pradilla、P. Fernandez

  DOI：10.1021/jo00004a002

  日期：1991.2

  The addition of organocyanocuprates to acylic allylic mesylates bearing a chiral sulfoxide in the 2-position occurs with complete S(N)2' regioselectivity, high E/Z stereoselectivity (15:1) and high asymmetric induction to produce enantiometrically pure trisubstituted vinyl sulfoxides.