3-羟基-1-金刚烷甲酸乙酯 | 122661-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-1-金刚烷甲酸乙酯
• 中文别名: 3-羟基金刚烷羧酸乙酯
• 英文名称: 1-Carbethoxy-3-hydroxyadamantane
• 英文别名: Ethyl 3-hydroxyadamantane-1-carboxylate
• CAS: 122661-59-0
• 化学式: C₁₃H₂₀O₃
• mdl: MFCD07783691
• 分子量: 224.3
• InChiKey: VVWVYPCOMWTLII-UHFFFAOYSA-N

物化性质

• 沸点：
  311.3±25.0℃ (760 Torr)
• 密度：
  1.245±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  125.4±15.9℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.923
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为产物：
  描述：

  3-羟基金刚烷-1-羧酸 以95%的产率得到
  参考文献：
  名称：

  MATSUI, AKIRA;JOSIDA, DZEHNITI;IKEHDA, KIESI;VATABEH, TAKASUKEH

  摘要：

  DOI：

文献信息

• Oxidation of Deactivated Cage Substrates in the System H2SO4–HNO3
  作者：E. A. Ivleva、I. S. Grinʼ、I. S. Uchaev、Yu. N. Klimochkin

  DOI：10.1134/s1070428020030082

  日期：2020.3

  the adamantane series in the system H2SO4–HNO3 have been studied, and the effective rate constants have been determined. The reaction is described by the pseudo-first-order kinetic equation. The primary kinetic isotope effect has been estimated at 2.9±0.3. The rate-determining step of the oxidation process is cleavage of the adamantane C–H bond. The presence of an ethyl group at the bridgehead position

  摘要研究了H 2 SO 4 -HNO 3体系中16种金刚烷系列羧酸酯的氧化动力学 ，并确定了有效的速率常数。该反应由拟一级动力学方程式描述。初步的动力学同位素效应估计为2.9±0.3。氧化过程的决定速率的步骤是金刚烷CH键的断裂。在桥头位置存在乙基会增加金刚烷底物对氧化的反应性，而甲基，乙氧羰基和乙氧羰基甲基会降低反应性。
• ADAMANTANE DERIVATIVES AND PROCESS FOR PRODUCING THEM
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP0927711A1

  公开（公告）日：1999-07-07

  In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2):    wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group; or R1 and R2 may bond together to form a double bond or an aromatic or non-aromatic ring; Y is O or OH and n = 1 to 3; or the imide compound and a co-catalyst (e.g., a transition metal compound), an adamantane derivative having a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is oxidized with oxygen. According to the above method, an adamantane derivative having a hydroxyl group together with a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is efficiently obtained.

  在存在式（2）所示的酰亚胺化合物（如 N-羟基邻苯二甲酰亚胺）的情况下： 其中 R1 和 R2 分别代表氢原子、卤素原子、烷基、芳基、环烷基；或 R1 和 R2 可键合在一起形成双键或芳香环或非芳香环；Y 为 O 或 OH，n = 1 至 3； 或亚胺化合物和助催化剂（如过渡金属化合物），具有诸如硝基、氨基、羟基、羧基、羟甲基和异氰酸基等官能团的金刚烷衍生物与氧发生氧化反应。根据上述方法，可有效地获得具有羟基和硝基、氨基、羟基、羧基、羟甲基和异氰酸基等官能团的金刚烷衍生物。
• Linear Free Energy Relationship Studies of the Dimethyldioxirane C-H Bond Insertion Reaction
  作者：Robert W. Murray、Hong Gu

  DOI：10.1021/jo00122a059

  日期：1995.9

  The relative rates of reaction of a series of p-substituted cumenes with dimethyldioxrane have been studied. The products are the corresponding cumyl alcohols. Treatment of the rate data with the Hammett substituent constants reveals that the insertion reaction is an electrophilic process with rho = -2.76. Similar treatment of the data with the Brown-Okamoto substituent constants gives rho(+) = -1.61. The second-order rate constants for the reaction of a series of substituted adamantanes with dimethyldioxirane were also determined. Again, the products are the corresponding adamantanols. The rate constants were correlated with several types of substituent constants. The best correlations were obtained with the Taft sigma(*) and sigma(I) constants which gave rho(*) = -1.08 and rho(I) -2.39, respectively. Thus, the insertion reaction in this aliphatic system is also electrophilic.
• US6392104B1
  申请人：——

  公开号：US6392104B1

  公开（公告）日：2002-05-21
• USRE39744E1
  申请人：——

  公开号：USRE39744E1

  公开（公告）日：2007-07-24