3-[(tert-butyldimethylsilyl)oxy]-2-phenylpropanal | 186199-35-9

• 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: 3-[(tert-butyldimethylsilyl)oxy]-2-phenylpropanal
• 英文别名: 3-[Tert-butyl(dimethyl)silyl]oxy-2-phenylpropanal
• CAS: 186199-35-9
• 化学式: C₁₅H₂₄O₂Si
• 分子量: 264.44
• InChiKey: VPNJPYOCYJZKRK-UHFFFAOYSA-N

物化性质

• 沸点：
  313.6±35.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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-[(tert-butyldimethylsilyl)oxy]-2-phenylpropanal 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 27.5h， 生成 2-苯基丁-3-烯-1-醇
  参考文献：
  名称：

  Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis

  摘要：

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.

  DOI：

  10.1021/jo951653e
• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 在 吡啶 、 4-二甲氨基吡啶 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-[(tert-butyldimethylsilyl)oxy]-2-phenylpropanal
  参考文献：
  名称：

  Influence of a 2-fluoro substituent on diastereoselectivity in the 1,3-dipolar cycloadditions of nitrones

  摘要：

  很明显，在氮酮的1,3-偶极环加成反应中，1,2-不对称诱导作用受到C-2位置氟原子存在的影响。通过三种不同方法合成的2-氟氮酮，与乙烯基乙醚进行了分子间的1,3-偶极环加成反应。所得异恶唑烷的立体结构通过其转化为2,7-二氧-6-氮杂双环[3.2.1]辛烷来确定。2-氟氮酮的非对映选择性与相应的2-羟氮酮相反。这一事实支持以下观点：氟原子与氮酮氧原子之间偶极排斥得到缓解的构象是2-氟氮酮的优选构象，而相应的2-羟氮酮则倾向于采取1,3-同系物应变最小的构象。

  DOI：

  10.1039/a702810e

文献信息

• [EN] TETRAHYDRO-IMIDAZO QUINOLINE COMPOSITIONS AS CBP/P300 INHIBITORS<br/>[FR] COMPOSITIONS DE TÉTRAHYDROIMIDAZO QUINOLÉINE UTILISÉES EN TANT QU'INHIBITEURS DE CBP/P300
  申请人：FORMA THERAPEUTICS INC

  公开号：WO2019055877A1

  公开（公告）日：2019-03-21

  The present disclosure is directed to inhibitors of the CBP/p300 family of bromodomains. The compounds can be useful in the treatment of disease or disorders associated with the inhibition of the CBP/p300 family of bromodomains. For instance, the disclosure is concerned with compounds and compositions for inhibition of the CBP/p300 family of bromodomains, methods of treating, preventing, or ameliorating diseases or disorders associated with the inhibition of CBP/p300 family of bromodomains, and methods of synthesis of these compounds.

  本公开内容涉及CBP/p300家族溴结构域的抑制剂。这些化合物可用于治疗与CBP/p300家族溴结构域抑制相关疾病或障碍。例如，本公开内容涉及用于抑制CBP/p300家族溴结构域的化合物和组合物，治疗、预防或改善与CBP/p300家族溴结构域抑制相关的疾病或障碍的方法，以及这些化合物的合成方法。
• New General Method for Regio- and Stereoselective Allylic Substitution with Aryl and Alkenyl Coppers Derived from Grignard Reagents
  作者：Yohei Kiyotsuka、Yuji Katayama、Hukum P. Acharya、Tomonori Hyodo、Yuichi Kobayashi

  DOI：10.1021/jo802426g

  日期：2009.3.6

  Allylic substitution with sp2-carbon reagents (aryl and alkenyl anions) was realized by using allylic picolinates and copper reagents derived from RMgBr and CuBr·Me2S to afford anti SN2′ products regio- and stereoselectively. Steric and electronic factors in the reagents and the size of the methylene substituents around the allylic moiety marginally affected the selectivity. The reaction system was

  通过使用烯丙基吡啶甲酸酯和衍生自RMgBr和CuBr·Me 2 S的铜试剂实现Sp 2-碳试剂（芳基和烯基阴离子）的烯丙基取代，可以在区域和立体选择性地提供抗S N 2'产物。试剂中的立体和电子因素以及烯丙基部分周围的亚甲基取代基的大小在一定程度上影响了选择性。该反应系统也与烷基试剂相容。此外，该取代被应用于四元中心的构建和（-）-倍半茶烯酚的合成。吸电子的C的吡啶基的性质和螯合（═ ö）-C 5 H ^ 4 Ñ到MgBr 2 发现原位产生的碳负责替代的高效率。
• Metalloporphyrin as an Efficient Catalyst in the Regioselective Isomerization of Epoxides to Carbonyl Compounds
  作者：Toshikatsu Takanami、Rina Hirabe、Masayoshi Ueno、Fumio Hino、Kohji Suda

  DOI：10.1246/cl.1996.1031

  日期：1996.12

  Regioselective ring-opening isomerization of epoxides to carbonyl compounds can effectively be catalyzed by iron (III) tetraphenylporphyrin, Fe(tpp)ClO4.

  环氧化物向羰基化合物的区域选择性开环异构化可以由铁 (III) 四苯基卟啉 Fe(tpp)ClO4 有效催化。
• Highly Regio- and Stereoselective Rearrangement of Epoxides to Aldehydes Catalyzed by High-Valent Metalloporphyrin Complex, Cr(TPP)OTf
  作者：Kohji Suda、Taketoshi Kikkawa、Shin-ichiro Nakajima、Toshikatsu Takanami

  DOI：10.1021/ja047104k

  日期：2004.8.1

  characteristic Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes. This Cr(TPP)OTf-catalyzed reaction is an operationally simple and especially convenient method for synthesizing optically active beta-siloxy aldehydes from 2,3-epoxy silyl ethers which are readily available in enantiomerically enriched forms by the Sharpless epoxidation of allylic alcohols followed

  三氟甲磺酸铬 (III) 四苯基卟啉三氟甲磺酸盐 Cr(TPP)OTf 在环氧化物向醛的区域和立体选择性重排中作为一种有效且具有特征性的路易斯酸催化剂起作用。这种 Cr(TPP)OTf 催化的反应是一种操作简单且特别方便的方法，用于从 2,3-环氧甲硅烷基醚合成光学活性 β-甲硅烷氧基醛，这些乙丙醚​​很容易通过烯丙醇的 Sharpless 环氧化以富含对映体的形式获得硅烷化。
• Influence of a 2-fluoro substituent on diastereoselectivity in the 1,3-dipolar cycloadditions of nitrones
  作者：Masataka Ihara、Yuko Tanaka、Nobuyuki Takahashi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1039/a702810e

  日期：——

  It is clear that the role of 1,2-asymmetric induction on the 1,3-dipolar cycloaddition of nitrones is influenced by the presence of a fluorine atom at the C-2 position. 2-Fluoro nitrones, synthesized by three different methods, have been subjected to the intermolecular 1,3-dipolar cycloaddition with ethyl vinyl ether. The stereostructures of isoxazolidines formed were determined by their conversion into 2,7-dioxa-6-azabicyclo[3.2.1]octanes. The diastereoselectivity of 2-fluoro nitrones was the reverse of that of the corresponding 2-hydro nitrones. This fact supports that the conformation with relief from the dipole repulsion between the fluorine atom and the oxygen atom of the nitrone is a preferred one for 2-fluoro nitrones, while the corresponding 2-hydro nitrones adopt the conformation with the least 1,3-allylic strain.

  很明显，在氮酮的1,3-偶极环加成反应中，1,2-不对称诱导作用受到C-2位置氟原子存在的影响。通过三种不同方法合成的2-氟氮酮，与乙烯基乙醚进行了分子间的1,3-偶极环加成反应。所得异恶唑烷的立体结构通过其转化为2,7-二氧-6-氮杂双环[3.2.1]辛烷来确定。2-氟氮酮的非对映选择性与相应的2-羟氮酮相反。这一事实支持以下观点：氟原子与氮酮氧原子之间偶极排斥得到缓解的构象是2-氟氮酮的优选构象，而相应的2-羟氮酮则倾向于采取1,3-同系物应变最小的构象。