methyl 3,5-dimethyladamantane-1-carboxylate | 24556-25-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3,5-dimethyladamantane-1-carboxylate
• 英文别名: 3,5-Dimethyladamantane-1-carboxylic acid, methyl ester
• CAS: 24556-25-0
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: KKHBYYBTKDEXEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.928
• 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：

  methyl 3,5-dimethyladamantane-1-carboxylate 在 triethylamine pentahydrogen fluoride salt 作用下， 以78%的产率得到methyl 3-fluoro-5,7-dimethyladamantane-1-carboxylate
  参考文献：
  名称：

  Synthesis of functionalized adamantanes from fluoroadamantanes

  摘要：

  Selective introduction of functional groups on the tert-carbon of adamantane was performed by substitution with fluorides. A methyl, phenacyl, aryl, cyclohexyl, alkoxy, or azido group was introduced into the adamantane skeleton without influencing the other functional groups present. Various functionalized adamantanes were synthesized using this scheme. A fluorinated analog of memantine (3-fluoro-5,7-dimethyl-1-adamantylammoniurn acetate 25) was synthesized from methyl 3,5-dimethyladamantane-1-carboxylate 6. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.059
• 作为产物：
  描述：

  methyl 3-fluoro-5-methyladamantane-1-carboxylate 、 三甲基铝 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到methyl 3,5-dimethyladamantane-1-carboxylate
  参考文献：
  名称：

  Synthesis of functionalized adamantanes from fluoroadamantanes

  摘要：

  Selective introduction of functional groups on the tert-carbon of adamantane was performed by substitution with fluorides. A methyl, phenacyl, aryl, cyclohexyl, alkoxy, or azido group was introduced into the adamantane skeleton without influencing the other functional groups present. Various functionalized adamantanes were synthesized using this scheme. A fluorinated analog of memantine (3-fluoro-5,7-dimethyl-1-adamantylammoniurn acetate 25) was synthesized from methyl 3,5-dimethyladamantane-1-carboxylate 6. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.059

文献信息

• Selective Phthalimido-N-oxyl (PINO)-Catalyzed C–H Cyanation of Adamantane Derivatives
  作者：Jan-Philipp Berndt、Frederik Erb、Lukas Ochmann、Jaqueline Beppler、Peter Schreiner

  DOI：10.1055/s-0037-1610403

  日期：2019.3

  present a new method for the selective C(sp3)–H cyanation of adamantane derivatives with PINO as the hydrogen abstracting reagent. A cyano radical is thereby transferred from p -toluenesulfonyl cyanide, allowing the cyanation of adamantane derivatives in up to 71% yield. The protocol presents a novel way to orthogonally functionalized adamantanes that are otherwise difficult to prepare. Mechanistic studies

  我们提出了一种以 PINO 作为夺氢试剂对金刚烷衍生物进行选择性 C(sp3)-H 氰化的新方法。氰基由此从对甲苯磺酰氰转移，使金刚烷衍生物氰化的产率高达 71%。该协议提出了一种新的方法来正交功能化金刚烷，否则很难制备。机理研究支持激进途径的假设。
• ADAMANTANE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1164125A1

  公开（公告）日：2001-12-19

  Adamantane derivatives are represented by Formula (1), (6) or (9) : [In Formula (1), R1 is a hydrogen atom or a methyl group; each of R2 and R3 is, identical to or different from each other, a hydrogen atom or a methyl group; each of A1 and A2 is, identical to or different from each other, a -C(=O)-O- group or -O-C(=O)- group, where the right-hand side of these two groups is on the adamantane ring side; each of X1 and X2 is, identical to or different from each other, a straight- or branched-chain alkylene group having 1 to 12 carbon atoms. In Formula (6), each of R4 and R5 is, identical to or different from each other, a hydrogen atom or a methyl group; each of R6 and R7 is, identical to or different from each other, a hydrogen atom or a methyl group; each of A3 and A4 is, identical to or different from each other, a group represented by the following formula:-A5-O-C(=O)- (wherein A5 is a straight- or branched-chain alkylene group having 1 to 6 carbon atoms, where the right-hand side of the above formula is on the adamantane ring side); X is a straight- or branched-chain alkylene group having 1 to 12 carbon atoms; and each of m and n is 0 or 1. In Formula (9), R8 is a hydrogen atom or a methyl group; each of R9 and R10 is, identical to or different from each other, a hydrogen atom or a methyl group; R11 is a hydrogen atom, a straight- or branched-chain alkyl group having 1 to 4 carbon atoms, or a group represented by the following Formula (10): (wherein R12 is an acryloyl group, methacryloyl group, 1-adamantylcarbonyl group or 3,5-dimethyladamant-1-ylcarbonyl group; and s is an integer from 1 to 6); and each of p, q and r is an integer from 1 to 6.] These adamantane derivatives are useful as, for example, raw materials for dental materials.

  金刚烷衍生物由式（1）、（6）或（9）表示： [在式(1)中，R1 是氢原子或甲基；R2 和 R3 各自是相同或不同的氢原子或甲基；A1和A2各自是相同或不同的-C(=O)-O-基团或-O-C(=O)-基团，其中这两个基团的右侧位于金刚烷环侧；X1和X2各自是相同或不同的具有1至12个碳原子的直链或支链亚烷基。在式(6)中，R4 和 R5 各自是相同或不同的氢原子或甲基；R6 和 R7 各自是相同或不同的氢原子或甲基；A3 和 A4 各自是相同或不同的下式所代表的基团：-A5-O-C(=O)-（其中 A5 是具有 1 至 6 个碳原子的直链或支链亚烷基，上式的右侧为金刚烷环侧）； X 是具有 1 至 12 个碳原子的直链或支链亚烷基；m 和 n 均为 0 或 1。在式 (9) 中，R8 是氢原子或甲基；R9 和 R10 各自是相同或不同的氢原子或甲基；R11 是氢原子、具有 1 至 4 个碳原子的直链或支链烷基或下式 (10) 所代表的基团： (其中 R12 为丙烯酰基、甲基丙烯酰基、1-金刚烷基羰基或 3,5-二甲基金刚烷-1-基羰基；s 为 1 至 6 的整数）；p、q 和 r 均为 1 至 6 的整数]。这些金刚烷衍生物可用作牙科材料的原料等。
• RADIATION-SENSITIVE RESIN COMPOSITION
  申请人：JSR Corporation

  公开号：EP1602975A1

  公开（公告）日：2005-12-07

  A radiation-sensitive resin composition comprising an acid-labile group-containing resin obtained by living radical polymerization having a specific structure which is insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid, and a photoacid generator, wherein the ratio of weight average molecular weight to number average molecular weight (weight average molecular weight/number average molecular weight) of the acid-labile group-containing-resin is smaller than 1.5.

  一种辐射敏感树脂组合物，包括一种通过活自由基聚合获得的具有特定结构的含酸基团树脂，该树脂不溶于碱或几乎不溶于碱，但在酸的作用下可溶于碱，还包括一种光酸发生器，其中含酸基团树脂的重量平均分子量与数量平均分子量之比（重量平均分子量/数量平均分子量）小于 1.5。
• FLUORINE-CONTAINING POLYMER, PURIFICATION METHOD, AND RADIATION-SENSITIVE RESIN COMPOSITION
  申请人：JSR Corporation

  公开号：EP2003148A2

  公开（公告）日：2008-12-17

  An object of the present invention is to provide a novel fluorine-containing polymer, a radiation-sensitive resin composition for liquid immersion lithography which contains the fluorine-containing polymer, which leads to a pattern having an excellent shape and excellent depth of focus, wherein the amount of an eluted component in a liquid for liquid immersion lithography such as water that comes in contact with the resist during exposure in liquid immersion lithography is little, and which provides a larger receding contact angle between the resist film and the liquid for liquid immersion lithography such as water, and a method for purifying the fluorine-containing polymer. The present resin composition comprises a novel fluorine-containing polymer (A) containing repeating units represented by the general formulae (1) and (2) and having Mw of 1,000-50,000, a resin (B) having an acid-unstable group, a radiation-sensitive acid generator (C), a nitrogen-containing compound (D) and a solvent (E).

  本发明的目的是提供一种新型含氟聚合物、一种用于液浸光刻的辐射敏感树脂组合物，该组合物含有该含氟聚合物，可使图案具有极佳的形状和极佳的焦深、其中，在液浸光刻过程中，液浸光刻用液体（如水）中与光刻胶接触的被洗脱成分的量很少，而且光刻胶膜与液浸光刻用液体（如水）之间的后退接触角较大；以及一种纯化含氟聚合物的方法。本树脂组合物包括含有通式（1）和（2）表示的重复单元且 Mw 为 1,000-50,000 的新型含氟聚合物（A）、具有酸不稳定基团的树脂（B）、辐射敏感酸发生器（C）、含氮化合物（D）和溶剂（E）。
• Fluorine-containing polymer, purification method, and radiation-sensitive resin composition
  申请人：JSR CORPORATION

  公开号：US10082733B2

  公开（公告）日：2018-09-25

  An object of the present invention is to provide a novel fluorine-containing polymer, a radiation-sensitive resin composition for liquid immersion lithography which contains the fluorine-containing polymer, which leads to a pattern having an excellent shape and excellent depth of focus, wherein the amount of an eluted component in a liquid for liquid immersion lithography such as water that comes in contact with the resist during exposure in liquid immersion lithography is little, and which provides a larger receding contact angle between the resist film and the liquid for liquid immersion lithography such as water, and a method for purifying the fluorine-containing polymer. The present resin composition comprises a novel fluorine-containing polymer (A) containing repeating units represented by the general formulae (1) and (2) and having Mw of 1,000-50,000, a resin (B) having an acid-unstable group, a radiation-sensitive acid generator (C), a nitrogen-containing compound (D) and a solvent (E).

  本发明的目的是提供一种新型含氟聚合物、一种用于液浸光刻的辐射敏感树脂组合物，该组合物含有该含氟聚合物，可使图案具有极佳的形状和极佳的焦深、其中，在液浸光刻过程中，液浸光刻用液体（如水）中与光刻胶接触的被洗脱成分的量很少，而且光刻胶膜与液浸光刻用液体（如水）之间的后退接触角较大；以及一种纯化含氟聚合物的方法。本树脂组合物包括含有通式（1）和（2）表示的重复单元且 Mw 为 1,000-50,000 的新型含氟聚合物（A）、具有酸不稳定基团的树脂（B）、辐射敏感酸发生器（C）、含氮化合物（D）和溶剂（E）。