3-(2-bromophenyl)-2,2-dimethylpropanoic acid methyl ester | 149080-23-9

• 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-(2-bromophenyl)-2,2-dimethylpropanoic acid methyl ester
• 英文别名: methyl 3-(2-bromophenyl)-2,2-dimethylpropanoate；2-Bromo-α,α-dimethylbenzenepropanoic acid, methyl ester
• CAS: 149080-23-9
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: VXWSOEJRNSVUFA-UHFFFAOYSA-N

物化性质

• 沸点：
  303.8±17.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-bromophenyl)-2,2-dimethylpropanoic acid methyl ester 在 氯化亚砜 、 十二羰基三钌 、 乙烯 、 水 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 160.0 ℃ 、1.72 MPa 条件下， 反应 123.0h， 生成 3-(2-bromobenzyl)-3-methyl-1-(pyridin-2-ylmethyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Highly Regioselective Carbonylation of Unactivated C(sp³)–H Bonds by Ruthenium Carbonyl

  摘要：

  The regioselective carbonylation of unactivated C(sp(3))-H bonds of aliphatic amides was achieved using Ru-3(CO)(12) as a catalyst. The presence of a 2-pyridinylmethylamine moiety in the amide is crucial for a successful reaction. The reaction shows a preference for C-H bonds of methyl groups as opposed to methylene C-H bonds and tolerates a variety of functional groups. The stoichiometric reaction of an amide with Ru-3(CO)(12) gave a dinuclear ruthenium complex in which the 2-pyridinylmethylamino moiety was coordinated to the ruthenium center in an N,N manner.

  DOI：

  10.1021/ja2001709
• 作为产物：
  描述：

  异丁酸甲酯 、 溴甲苯 在 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 3-(2-bromophenyl)-2,2-dimethylpropanoic acid methyl ester
  参考文献：
  名称：

  芳香族胺衍生物有机电致发光材料及其器件

  摘要：

  公开了芳香族胺衍生物有机电致发光材料及其器件。所述化合物为芳香族胺取代的芘类化合物，其中所述化合物中芳胺的其中一个芳基具有取代的六元(杂)芳环并饱和环的结构，另一个芳基为取代的(杂)芳基。所述化合物可用作有机电致发光器件中发光材料。这些新型化合物能提供更好的器件性能，如更窄的半峰宽和更高的外量子效率。还公开了一种电致发光器件和化合物配方。

  公开号：

  CN113683518A

文献信息

• Total Synthesis of (Nor)illudalane Sesquiterpenes Based on a C(sp³)–H Activation Strategy
  作者：Romain Melot、Marcus V. Craveiro、Olivier Baudoin

  DOI：10.1021/acs.joc.9b01669

  日期：2019.10.18

  Three (nor)illudalane sesquiterpenes were synthesized from a common intermediate in racemic and enantioenriched forms using Pd0-catalyzed C(sp3)-H arylation as a key step. The configuration of the isolated, highly symmetric quaternary stereocenter of the target molecules was controlled through a matched combination of chiral substrate and catalyst. Moreover, the recently developed Ir-catalyzed C-H

  使用Pd0催化的C（sp3）-H芳基化为关键步骤，从外消旋和对映体富集形式的一种常见中间体合成了三（正）伊拉达拉烷倍半萜。通过手性底物和催化剂的匹配组合来控制靶分子的分离的，高度对称的四元立体中心的构型。此外，采用最近开发的Ir催化的CH硼化/ Cu催化的甲基化方法将甲基安装在苯环上。这种策略允许高效合成外消旋和（S）构型的嘌呤奎尼酸，地喹醌和russujaponol F.
• Gem-dialkyl-7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0544287A1

  公开（公告）日：1993-06-02

  Gem-dialkyl-7-oxabicycloheptane substituted prostaglandin analogs useful in treating thrombotic and vasospastic disease have the structural formula wherein m is 1, 2 or 3; n is 0, 1, 2, 3 or 4; Z is -(CH₂)₂-, -CH=CH- or with the proviso when Z is -CH=CH-, n is l, 2, 3 or 4; R is CO₂H, CO₂lower alkyl, or CO₂alkali metal, X is O or NH; and where R¹ and R² are as defined herein and R³ and R⁴ are each independently alkyl, or R³ and R⁴ may be taken together with the carbon to which it is attached to form a 3- or 4-membered ring.

  Gem-二烷基-7-氧杂双环庚烷基取代前列腺素类似物在治疗血栓性和血管痉挛性疾病方面有用，其结构式为m为1、2或3；n为0、1、2、3或4；Z为-(CH₂)₂-，-CH=CH-或者在Z为-CH=CH-时，n为1、2、3或4；R为CO₂H、CO₂较低烷基，或CO₂碱金属，X为O或NH；其中R¹和R²如上所定义，R³和R⁴各自独立为烷基，或R³和R⁴可以与其附着的碳一起形成3-或4-成员环。
• Interphenylene 7-oxabicyclo[2.2.1]heptane oxazoles. Highly potent, selective, and long-acting thromboxane A2 receptor antagonists
  作者：Raj N. Misra、Baerbel R. Brown、Philip M. Sher、Manorama M. Patel、Steven E. Hall、Wen Ching Han、Joel C. Barrish、Octavian Kocy、Don N. Harris

  DOI：10.1021/jm00062a013

  日期：1993.5

  A series of interphenylene 7-oxabicyclo[2.2.1]heptane oxazoles (2) were prepared and evaluated for their thromboxane (TxA2) antagonistic activity in vitro and duration of action in vivo. Examination of the carboxyl side chain indicated that the interphenylene ring substitution pattern and, to a lesser extent, chain length were important factors in determining TxA2 antagonistic potency. For the carboxyl side chain, ortho substitution, a single methylene spacer between the interphenylene and oxabicycloheptane rings, and a propionic acid side-chain length were determined to be optimal. With respect to the oxazole side chain a wide range of amide substituents with diverse structures and lipophilicities were compatible with potent antagonistic activity. Finally. an acidic functional group on the alpha-chain and a hydrogen bond acceptor on the 4-position of the oxazole ring were critical for potent activity. From the analogs prepared 42 BMS-180,291: [(+)-1S-(1alpha,2alpha,3alpha,4alpha)]-2-[[3-[4-[(n-pentylamino)carbonyl]-2-oxazolyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid} was found to be a potent, selective, and orally-active TxA2 antagonist with a long duration of action and has been selected as a candidate for clinical development. In human platelet-rich plasma, 42 inhibited arachidonic acid (800 muM) and U-46,619 (10 muM) induced aggregation with I50 values of 7 and 21 nM, respectively. Radioligand binding studies of 42 with [H-3]-SQ 29,548 showed a K(d) value of 4.0 +/- 1.0 nM in human platelet membranes. Both in vitro and in vivo studies indicated 42 was devoid of direct agonistic activity. In vivo 42 (0.2 mg/kg, po) showed extended protection (T50 = 14.4 h) from U-46,619 (2 mg/kg, iv) induced death in mice, and a single oral dose of 42 (3 mg/kg) abolished U46,619-induced platelet aggregation ex vivo in African green monkeys for >24 h.