4-(tert-butyldimethylsiloxy)-1-(dimethyl (phenyl)silyl)butan-1-one | 1240781-65-0

• 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: 4-(tert-butyldimethylsiloxy)-1-(dimethyl (phenyl)silyl)butan-1-one
• 英文别名: 4-[Tert-butyl(dimethyl)silyl]oxy-1-[dimethyl(phenyl)silyl]butan-1-one；4-[tert-butyl(dimethyl)silyl]oxy-1-[dimethyl(phenyl)silyl]butan-1-one
• CAS: 1240781-65-0
• 化学式: C₁₈H₃₂O₂Si₂
• 分子量: 336.622
• InChiKey: WNUAPJXVLGETQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tert-butyldimethylsiloxy)-1-(dimethyl (phenyl)silyl)butan-1-one 在 3-乙基-5-(2-羟乙基)-4-甲基噻唑溴化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 12.0h， 以40%的产率得到9-hydroxy-2,2,3,3,14,14,15,15-octamethyl-4,13-dioxa-3,14-disilahexadecan-8-one
  参考文献：
  名称：

  Convergent Access to Bis-spiroacetals through a Sila-Stetter–Ketalization Cascade

  摘要：

  An NHC-catalyzed sila-Stetter reaction between aliphatic acylsilanes and vinylketones bearing silyl ether substituents affords functionalized 1,4-diketones, which upon treatment under acidic conditions leads to the corresponding bis-spiroacetals. The two-step sequence may also be carried out in a one-pot operation leading to high yields of the desired bis-spiroacetals.

  DOI：

  10.1021/ol402017x
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 以 四氢呋喃 为溶剂， 反应 62.0h， 生成 4-(tert-butyldimethylsiloxy)-1-(dimethyl (phenyl)silyl)butan-1-one
  参考文献：
  名称：

  Convergent Access to Bis-spiroacetals through a Sila-Stetter–Ketalization Cascade

  摘要：

  An NHC-catalyzed sila-Stetter reaction between aliphatic acylsilanes and vinylketones bearing silyl ether substituents affords functionalized 1,4-diketones, which upon treatment under acidic conditions leads to the corresponding bis-spiroacetals. The two-step sequence may also be carried out in a one-pot operation leading to high yields of the desired bis-spiroacetals.

  DOI：

  10.1021/ol402017x

文献信息

• Stereoselective Syntheses of Trisubstituted Olefins via Platinum Catalysis: α-Silylenones with Geometrical Complementarity
  作者：Douglas A. Rooke、Eric M. Ferreira

  DOI：10.1021/ja1058197

  日期：2010.9.1

  The stereoselective syntheses of alpha-silylenones using catalytic PtCl(2) are reported. Via alkyne activation, alpha-hydroxypropargylsilanes are converted to (Z)-silylenones through a highly selective silicon migration. The complementary (E)-silylenones are accessed by a regioselective hydrosilylation of the ynone precursor. The synthetic utility of these compounds is demonstrated in cross-coupling

  报道了使用催化 PtCl(2) 立体选择性合成 alpha-silylenones。通过炔烃活化，α-羟基炔丙基硅烷通过高度选择性的硅迁移转化为 (Z)-甲硅烷酮。互补的 (E)-甲硅烷基酮通过炔酮前体的区域选择性氢化硅烷化获得。这些化合物的合成效用在交叉偶联反应中得到证明，突出了这些协议在合成几何定义的三取代烯烃方面的潜力。
• Stereoselective Synthesis of Tetrasubstituted Olefins through a Halogen-Induced 1,2-Silyl Migration
  作者：Nicholas T. Barczak、Douglas A. Rooke、Zachary A. Menard、Eric M. Ferreira

  DOI：10.1002/anie.201303007

  日期：2013.7.15

  Migrating through Si valley: The highly stereoselective formation of α‐silyl‐β‐ haloenones by way of silicon group migration is described. Electrophilic activation of the alkyne by N‐halosuccinimides induced an anti‐selective migration to give highly substituted enones (see scheme). These enone products can be readily converted to the all‐carbon tetrasubstituted alkenes while maintaining their geometry

  穿过硅谷迁移：描述了通过硅基团迁移而高度立体选择性形成α-甲硅烷基-β-芦荟酮。N-卤代琥珀酰亚胺对炔烃的亲电活化可引起反选择性迁移，从而得到高度取代的烯酮（参见方案）。这些烯酮产物可以容易地转化为全碳四取代烯烃，同时保持其几何形状。
• CARBOXYLATE SALT OR SULFONATE SALT, AND SURFACTANT
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20200024219A1

  公开（公告）日：2020-01-23

  A carboxylic acid or sulfonic acid salt containing a plurality of carbonyl groups, and a surfactant represented by the following formula: R 1 —C(═O)—R 2 —C(═O)—R 3 -A wherein R 1 , R 2 and R 3 are as defined herein, and A is —COOX or —SO 3 X, wherein X is H, a metal atom, NR 4 4 , imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent, where R 4 s are each H or an organic group and are the same as or different from each other; and any two of R 1 , R 2 , and R 3 optionally bind to each other to form a ring.

  一种含有多个羰基基团的羧酸或磺酸盐，以及由以下公式表示的表面活性剂：R1—C(═O)—R2—C(═O)—R3-A，其中R1、R2和R3如本文所定义，A为—COOX或—SO3X，其中X为H、金属原子、NR44、含有取代基的咪唑离子、含有取代基的吡啶离子或含有取代基的膦离子，其中R4分别为H或有机基团，且相互相同或不同；R1、R2和R3中的任意两个可以选择性地结合形成环。
• SULFURIC ACID ESTER OR SALT THEREOF, AND SURFACTANT
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20200172476A1

  公开（公告）日：2020-06-04

  A sulfuric acid ester containing a plurality of carbonyl groups or a salt thereof, and a surfactant. The sulfuric acid ester is a compound represented by the following formula: R 1 —C(═O)—R 2 —C(═O)—R 3 —OSO 3 X wherein R 1 , R 2 and R 3 are as defined herein; X is H, a metal atom, NR 4 4 , imidazolium optionally containing a substituent, pyridinium optionally containing a substituent, or phosphonium optionally containing a substituent, where R 4 s are each H or an organic group and are the same as or different from each other; and any two of R 1 , R 2 , and R 3 optionally bind to each other to form a ring.

  含有多个羰基基团的硫酸酯或其盐，以及表面活性剂。硫酸酯化合物由以下式子表示：R1—C(═O)—R2—C(═O)—R3—OSO3X，其中R1，R2和R3如定义所示；X是H，金属原子，NR44，含有取代基的咪唑离子，含有取代基的吡啶离子或含有取代基的磷离子，其中R4分别为H或有机基团，且彼此相同或不同；R1，R2和R3中的任意两个可以选择结合形成环。
• Convergent Access to Bis-spiroacetals through a Sila-Stetter–Ketalization Cascade
  作者：Jessica Labarre-Lainé、Redouane Beniazza、Valérie Desvergnes、Yannick Landais

  DOI：10.1021/ol402017x

  日期：2013.9.20

  An NHC-catalyzed sila-Stetter reaction between aliphatic acylsilanes and vinylketones bearing silyl ether substituents affords functionalized 1,4-diketones, which upon treatment under acidic conditions leads to the corresponding bis-spiroacetals. The two-step sequence may also be carried out in a one-pot operation leading to high yields of the desired bis-spiroacetals.