cinnamic acid adamantyl ester

• 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: cinnamic acid adamantyl ester
• 英文别名: (E)-adamantan-1-ylcinnamate；1-adamantyl (E)-3-phenylprop-2-enoate
• 化学式: C₁₉H₂₂O₂
• 分子量: 282.382
• InChiKey: QFNOPYTULISOBR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  5.0
• 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

• 作为产物：
  描述：

  2-((3r,5r,7r)-adamantan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 二氟化氢钾 、 tert-butylammonium hexafluorophosphate(V) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 cinnamic acid adamantyl ester
  参考文献：
  名称：

  通过烷基有机硼试剂的电化学功能化引入杂原子的统一合成策略

  摘要：

  基于系统电化学分析，建立了C(sp 3 ) 基有机硼化合物的综合合成平台，用于引入杂原子。电化学介导的成键策略被证明对 sp 3的功能化非常有效-具有显着空间位阻的杂化碳原子。此外，几乎所有非金属杂原子都可以使用一个统一的协议作为反应伙伴。观察到的反应性源于底物的两个连续的单电子氧化，最终产生一个极具反应性的碳正离子作为关键中间体。详细的反应曲线可以通过多方面的电化学研究来阐明。最终，通过电化学驱动的反应发展，实现了有机硼化合物活化策略的新维度。

  DOI：

  10.1021/jacs.2c03213

文献信息

• [EN] LATENT ACIDS AND THEIR USE<br/>[FR] ACIDES LATENTS ET LEUR UTILISATION
  申请人：BASF SE

  公开号：WO2016124493A1

  公开（公告）日：2016-08-11

  Compounds of the formula (I) and (IA) wherein X is -O(CO)-; R1 is C1-C12haloalkyl or C6-C10haloaryl; R2 is located in position 7 of the coumarinyl ring and is OR8; R2a, R2b and R2C independently of each other are hydrogen; R3 is C1-C8haloalkyl or C1-C8haloalkyl; R4 is hydrogen; and R8 is C1-C6alkyI; are suitable as photosensitive acid donors in the preparation of photoresist compositions such as used for example in the preparation of spacers, insulating layers, interlayer dielectric films, insulation layers, planarization layers, protecting layers, overcoat layers, banks for electroluminescence displays and liquid crystal displays (LCD).

  化合物的化学式（I）和（IA），其中X为-O(CO)-；R1为C1-C12卤代烷基或C6-C10卤代芳基；R2位于香豆素环的第7位，为OR8；R2a、R2b和R2C彼此独立地为氢；R3为C1-C8卤代烷基或C1-C8卤代烷基；R4为氢；R8为C1-C6烷基，适用于作为感光酸给体，用于制备光刻胶组合物，例如用于制备间隔层、绝缘层、层间介质膜、绝缘层、平坦化层、保护层、覆盖层、电致发光显示器和液晶显示器（LCD）的制备。
• [EN] CARBORANE-BASED HISTONE DEACETYLASE (HDAC) INHIBITORS<br/>[FR] INHIBITEURS D'HISTONE DÉSACÉTYLASE (HDAC) À BASE DE CARBORANE
  申请人：UNIV CALIFORNIA

  公开号：WO2020117976A1

  公开（公告）日：2020-06-11

  The present disclosure provides compounds and compositions capable of treating cancer, a disease of the central nervous system, and an inflammatory autoimmune disease, and methods of use thereof.

  本公开提供了能够治疗癌症、中枢神经系统疾病以及炎症性自身免疫疾病的化合物和组合物，以及它们的使用方法。
• Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester
  作者：Jan Glaser、Martina Schultheis、Sudipta Hazra、Banasri Hazra、Heidrun Moll、Uta Schurigt、Ulrike Holzgrabe

  DOI：10.3390/molecules19021394

  日期：——

  Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC50 = 48.8 µM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.

  在对 Valeriana wallichii (V. wallichii) 根茎的氯仿提取物进行生物测定引导的分馏时，成功分离并鉴定出咖啡酸伯基酯 (1)，作为对 Leishmania major (L. major) 萌发体的活性成分（IC50 = 48.8 µM）。为了研究结构-活性关系 (SAR)，基于化合物 1 合成了一系列化合物，并在体外测试了它们对 L. major 和 L. donovani 萌发体和 L. major 非芽孢体的活性。通过使用鼠类 J774.1 细胞系和骨髓来源的巨噬细胞 (BMDM) 测定了细胞毒性。一些化合物在与标准药物五氟苯和米氟喹范围内的浓度下表现出抗利什曼病活性。在 L. major 非芽孢体实验中，化合物 15、19 和 20 显示出良好的活性，同时对 BMDM 的细胞毒性相对较低，产生了可接受的选择性指数。相邻的酚羟基化合物对鼠类细胞系 J774.1 和 BMDM 显示出较高的细胞毒性。Michael 体系似乎对于抗利什曼病活性并不是必需的。根据结果，化合物 27 可被视为进一步结构优化的新型先导结构。
• [EN] SULFONIUM DERIVATIVES AND THE USE THEROF AS LATENT ACIDS<br/>[FR] DÉRIVÉS DE SULFONIUM ET LEUR UTILISATION EN TANT QU'ACIDES LATENTS
  申请人：BASF SE

  公开号：WO2010046240A1

  公开（公告）日：2010-04-29

  Compounds of the formula (I), wherein Ar1 is for example phenylene or biphenylene both unsubstituted or substituted; Ar2 and Ar3 are for example independently of each other phenyl, naphthyl, biphenylylyl or heteroaryl, all optionally substituted; or Ar1 and Ar2 for example together with a direct bond, O, S or (CO), form a fused ring system; R is for example hydrogen, C3-C30cycloalkyl or C1-C18alkyl; and R1, R2 and R3 independently of each other are for example C1-C10haloalkyl; are effective photoacid generators (PAG).

  化合物的公式（I），其中Ar1例如是未取代或取代的苯基或联苯基; Ar2和Ar3例如是独立的苯基，萘基，联苯基或杂环基，均可选取代; 或者例如Ar1和Ar2与直接键，O，S或（CO）一起形成融合的环系统; R例如是氢，C3-C30环烷基或C1-C18烷基; R1，R2和R3独立地例如是C1-C10卤代烷基; 是有效的光酸发生剂（PAG）。
• [EN] SULPHONIUM SALT INITIATORS<br/>[FR] INITIATEURS À BASE DE SELS DE SULFONIUM
  申请人：CIBA HOLDING INC

  公开号：WO2009047151A1

  公开（公告）日：2009-04-16

  Compounds of the formula (I), wherein X is a single bond, CRaRb O, S, NRC, NCORC, CO, SO or SO2; L, L1, L2, L3, L4, L5, L6, L7 and L8 are for example hydrogen, R1 or COT; T denotes T1 or O-T2; T1 and T2 for example are hydrogen, C1-C20alkyl, C3-C12cycloalkyl, C2-C20alkenyl, C5- C12cycloalkenyl, C6-C14aryl, C3-C12heteroaryl, C1-C20alkyl substituted by one or more D, C2- C20alkyl interrupted by one or more E, C2-C20alkyl substituted by one or more D and inter- rupted by one or more E or Q; R1, R2, R3, R4, Ra, Rb and Rc are T1; D is for example R5, OR5, SR5 or Q1; E is for example O, S, COO or Q2; R5 and R6 for example are hydrogen, C1- C12alkyl or phenyl; Q is for example C6-C12bicycloalkyl, C6-C12bicycloalkenyl or C6- C12tricycloalkyl; Q1 is for example, C6-C14aryl or C3-C12heteroaryl; Q2 is for example C6- C14arylene or C3-C12heteroarylene; Y is an anion; and M is a cation; provided that at least one of L, L1, L2, L3, L4, L5, L6, L7 and L8 is other than hydrogen; and provided that (i) at least one of T1 or T2 is a group Q; or (ii) at least one D is a group Q1; or (iii) at least one E is a group Q2; are suitable as photolatent catalysts.

  化合物的式子（I），其中X是单键，CRaRb O，S，NRC，NCORC，CO，SO或SO2; L，L1，L2，L3，L4，L5，L6，L7和L8例如是氢，R1或COT; T表示T1或O-T2; T1和T2例如是氢，C1-C20烷基，C3-C12环烷基，C2-C20烯基，C5-C12环烯基，C6-C14芳基，C3-C12杂芳基，被一个或多个D取代的C1-C20烷基，被一个或多个E中断的C2-C20烷基，被一个或多个D取代并被一个或多个E或Q中断的C2-C20烷基; R1，R2，R3，R4，Ra，Rb和Rc是T1; D例如是R5，OR5，SR5或Q1; E例如是O，S，COO或Q2; R5和R6例如是氢，C1-C12烷基或苯基; Q例如是C6-C12双环烷基，C6-C12双环烯基或C6-C12三环烷基; Q1例如是C6-C14芳基或C3-C12杂芳基; Q2例如是C6-C14芳撑基或C3-C12杂芳撑基; Y是阴离子; M是阳离子; 前提是L，L1，L2，L3，L4，L5，L6，L7和L8中至少有一个不是氢; 并且前提是（i）至少有一个T1或T2是Q组; 或（ii）至少有一个D是Q1组; 或（iii）至少有一个E是Q2组; 适用于光潜催化剂。