3-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acryloyl chloride | 159534-29-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acryloyl chloride
• 英文别名: 2-<(tert-Butyldimethylsilyl)oxy>cinnamoyl chloride；(E)-3-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-enoyl chloride
• CAS: 159534-29-9
• 化学式: C₁₅H₂₁ClO₂Si
• 分子量: 296.869
• InChiKey: FXBKGWPASCNAMD-ZHACJKMWSA-N

物化性质

• 沸点：
  340.7±25.0 °C(predicted)
• 密度：
  1.055±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acryloyl chloride 在 氢氟酸 作用下， 生成 2-Methyl-4,6-dinitrophenyl 2'-hydroxycinnamate
  参考文献：
  名称：

  Associative and Dissociative Pathways in the Alkaline Hydrolysis of Aryl 2-Hydroxycinnamates

  摘要：

  Aryl 2-hydroxycinnamate esters hydrolyze in alkaline solutions (20% dioxane-water v/v) obeying the rate law k(obs) = k(2) + k(b)[OH-]/(1 + a(H)/K-a), where K-a is the ionization constant of the hydroxy group of the ester and kb is the second-order rate constant for the attack of hydroxide ion on the ionized ester. Kinetic data and activation parameters for the hydrolysis of the 2,4-dinitrophenyl ester show that the mechanism giving rise to the k(a) term cannot be a simple B(Ac)2 type process and suggest the occurrence of a E1cB mechanism involving an ''extended'' o-oxoketene intermediate. The Bronsted plot of the apparent second-order rate constants (k(a)K(a)/k(w)) versus the pK of the leaving group indicates that the reaction mechanism changes from E1cB to B(Ac)2 for esters with leaving groups having pK higher than about 6.

  DOI：

  10.1021/jo00106a016
• 作为产物：
  描述：

  反式-2-羟基肉桂酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 生成 3-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acryloyl chloride
  参考文献：
  名称：

  Associative and Dissociative Pathways in the Alkaline Hydrolysis of Aryl 2-Hydroxycinnamates

  摘要：

  Aryl 2-hydroxycinnamate esters hydrolyze in alkaline solutions (20% dioxane-water v/v) obeying the rate law k(obs) = k(2) + k(b)[OH-]/(1 + a(H)/K-a), where K-a is the ionization constant of the hydroxy group of the ester and kb is the second-order rate constant for the attack of hydroxide ion on the ionized ester. Kinetic data and activation parameters for the hydrolysis of the 2,4-dinitrophenyl ester show that the mechanism giving rise to the k(a) term cannot be a simple B(Ac)2 type process and suggest the occurrence of a E1cB mechanism involving an ''extended'' o-oxoketene intermediate. The Bronsted plot of the apparent second-order rate constants (k(a)K(a)/k(w)) versus the pK of the leaving group indicates that the reaction mechanism changes from E1cB to B(Ac)2 for esters with leaving groups having pK higher than about 6.

  DOI：

  10.1021/jo00106a016

文献信息

• Compounds having protected hydroxy groups
  申请人：Givaudan SA

  公开号：US06437150B1

  公开（公告）日：2002-08-20

  The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

  本发明涉及具有保护羟基的化合物的公式(I)。这些化合物是感官剂（如香料）、掩蔽剂和抗微生物剂的前体。当激活时，公式(I)的化合物被裂解并形成一个或多个感官和/或抗微生物化合物。
• Oxygenated Analogues of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as Potential Extended-Action Cocaine-Abuse Therapeutic Agents
  作者：David B. Lewis、Dorota Matecka、Ying Zhang、Ling-Wei Hsin、Christina M. Dersch、David Stafford、John R. Glowa、Richard B. Rothman、Kenner C. Rice

  DOI：10.1021/jm990291q

  日期：1999.12.2

  An investigation into the preparation of potential extended-release cocaine-abuse therapeutic agents afforded a series of compounds related to 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (1a) and 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (1b) (GBR 12935 and GBR 12909, respectively), which were designed, synthesized, and evaluated for their ability to bind to

  对潜在的可卡因滥用滥用治疗剂的制备进行了研究，得到了一系列与1- [2-（二苯基甲氧基）乙基] -4-（3-苯基丙基）哌嗪（1a）和1- [2- [双（4-氟苯基）甲氧基]乙基] -4-（3-苯基丙基）哌嗪（分别为GBR 12935和GBR 12909），已设计，合成并评估了其与多巴胺转运蛋白的结合能力（DAT）并抑制[（3）H]标记的多巴胺（DA）的摄取。在1a-1d的苯丙基部分的苯环上加成羟基和甲氧基取代基会产生一系列有效的DAT配体（选择性5-28）。包括羟基以将中链羧酸酯结合到分子中，形成油溶性前药，适合“长效” 注射技术。在丙基侧链上引入含氧官能团后，得到的酮29和30大大降低了对DAT的亲和力，并降低了抑制[（3）H] DA和苯甲醇31-36的吸收能力，它们在结合DAT和抑制[（3）H] DA摄取方面具有很高的效力和选择性。32个对映体（34和36）在生物学测试中几乎相同。化合
• Aryl-acrylic acid esters
  申请人：Givaudan Roure (International) SA

  公开号：US06096918A1

  公开（公告）日：2000-08-01

  The acrylic acid esters of Formula I are useful for the delivery of organoleptic compounds, especially for flavors, fragrances, masking agents and antimicrobial compounds. They can also deliver fluorescent whitening agents.

  公式I的丙烯酸酯对于传递有机感官化合物非常有用，特别是用于香料、香气、掩蔽剂和抗微生物化合物。它们还可以传递荧光增白剂。