neopentyl bromoacetate | 101001-73-4

• 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: neopentyl bromoacetate
• 英文别名: 2,2-dimethylpropyl 2-bromoacetate
• CAS: 101001-73-4
• 化学式: C₇H₁₃BrO₂
• 分子量: 209.083
• InChiKey: YMFWXAPAYFRXMT-UHFFFAOYSA-N

物化性质

• 沸点：
  181.6±8.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  neopentyl bromoacetate 在 sodium carbonate 、 三乙胺 、 三甲基膦 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of 1,3-Dioxan-4-ylidenes

  摘要：

  A phosphine-catalyzed reaction of an allenoate with aldehydes furnished (2,6-diaryl-[1,3]dioxan-4-ylidene)-acetates 4 in excellent to moderate yields with complete diastereoselectivity and high E/Z-selectivities. Upon removal of the acetal functionality in this domino reaction product 4, delta-hydroxy-beta-ketoester 11 was obtained. The reported vinylphosphonium-based approach provides a new way to achieve a synthesis of 6-hydroxy-beta-ketoesters that differs from the classical dianion-based approach.

  DOI：

  10.1021/ol050203y
• 作为产物：
  描述：

  新戊醇 、 溴乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 neopentyl bromoacetate
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 8. Pharmacological Optimization of Orally Bioavailable 2-Pyridone-Containing Peptidomimetics

  摘要：

  The optimization of the pharmacokinetic performance of various 2-pyridone-containing human rhinovirus (HRV) 3C protease (3CP) inhibitors following oral administration to either beagle dogs or CM-monkeys is described. The molecules described in this work are composed of a 2-pyridone-containing peptidomimetic binding determinant and an alpha,beta-unsaturated ester Michael acceptor moiety which forms an irreversible covalent adduct with the active site cysteine residue of the 3C enzyme. Modification of the ester contained within these compounds is detailed along with alteration of the P-2 substituent present in the peptidomimetic portion of the inhibitors. The pharmacokinetics of several inhibitors in both dogs and monkeys are described (7 h plasma concentrations after oral administration) along with their human plasma stabilities, stabilities in incubations with human, dog, and monkey microsomes and hepatocytes, Caco-2 permeabilities, and aqueous solubilities. Compounds containing an alpha,beta-unsaturated ethyl ester fragment and either an ethyl or propargyl. P-2 moiety displayed the most promising combination of 3C enzyme inhibition (k(obs)/[1] 170 000-223 000 M-1 s(-1)), antiviral activity (EC50 = 0.047-0.058 muM, mean vs seven HRV serotypes), and pharmacokinetics following oral administration (7 h dog plasma levels = 0.248-0.682 muM; 7 h CM-monkey plasma levels = 0.057-0.896 muM).

  DOI：

  10.1021/jm030166l

文献信息

• Amine-catalyzed tunable reactions of allenoates with dithioesters: formal [4+2] and [2+2] cycloadditions for the synthesis of 2,3-dihydro-1,4-oxathiines and enantioenriched thietanes
  作者：Hai-Bin Yang、Yu-Chao Yuan、Yin Wei、Min Shi

  DOI：10.1039/c5cc01313e

  日期：——

  The chemoselective [4+2] vs. [2+2] cycloaddition between allenoates and dithioesters has been developed on the basis of switching the nucleophilic amine catalyst, offering a divergent synthesis of sulfur-containing heterocycles.

  已开发出基于切换亲核胺催化剂的烯酸酯和二硫酯之间的化学选择性[4+2] vs. [2+2]环加成反应，提供了含硫杂环化合物的分岔合成。
• Prodrugs of thrombin inhibitors
  申请人：AstraZeneca AB

  公开号：US20040162410A1

  公开（公告）日：2004-08-19

  There is provided compounds of formula I, R 1 O(O)C—CH 2 —(R)Cgl-Aze-Pab-R 2 I wherein R 1 and R 2 have meanings given in the description, which are useful as prodrugs of inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (eg thrombosis) or as anticoagulants.

  提供了公式I，其中包含化合物，R1O(O)C—CH2—(R)Cgl-Aze-Pab-R2I，其中R1和R2的含义如说明中所述，这些化合物可用作类似胰蛋白酶的抑制剂的前药，如凝血酶，并且特别适用于治疗需要抑制凝血酶的情况（例如血栓形成）或作为抗凝剂。
• Photocatalytic 1,2-oxo-alkylation reaction of styrenes with diazoacetates
  作者：Fang Li、Siqi Zhu、Rene M. Koenigs

  DOI：10.1039/d2cc02414d

  日期：——

  reactivity of diazoalkanes can be suppressed and a 1,2 oxo-alkylation reaction can be achieved (32 examples, up to 94% yield) without the formation of cyclopropane by-products via the formation of radical intermediates from ethyl diazoacetate.

  我们报告了苯乙烯与仅受体重氮烷的光催化 1,2-双官能化反应。在 DABCO 和t BuOOH 的存在下，可以抑制重氮烷烃的卡宾反应性，并且可以实现 1,2 氧代烷基化反应（32 个实例，高达 94% 的产率），而不会通过形成生成环丙烷副产物来自重氮乙酸乙酯的自由基中间体。
• C‐H Functionalization of Heterocycles with Triplet Carbenes by means of an Unexpected 1,2‐Alkyl Radical Migration
  作者：Claire Empel、Sripati Jana、Łukasz Ciszewski、Katarzyna Zawada、Chao Pei、Dorota Gryko、Rene M. Koenigs

  DOI：10.1002/chem.202300214

  日期：——

  A triplet carbene is involved in the C3-H functionalization of indole heterocycles. We herein describe a combined experimental and computational study on this reaction and unveil an unexpected 1,2-alkyl radical migration pathway.

  三线态卡宾参与吲哚杂环的 C3-H 官能化。我们在此描述了对该反应的综合实验和计算研究，并揭示了一种意想不到的 1,2-烷基自由基迁移途径。
• Prodrugs of Thrombin inhibitors
  申请人：Astra Aktiebolag

  公开号：EP0995755A1

  公开（公告）日：2000-04-26

  There is provided compounds of formula I,         R1O(O)C-CH2-(R)Cgl-Aze-Pab-R2     I wherein R1 and R2 have meanings given in the description, which are useful as prodrugs of inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (eg thrombosis) or as anticoagulants.

  提供了式 I 的化合物、 R1O(O)C-CH2-(R)Cgl-Aze-Pab-R2 I 其中 R1 和 R2 的含义见说明，可用作胰蛋白酶样蛋白酶（如凝血酶）抑制剂的原药，特别是用于治疗需要抑制凝血酶的病症（如血栓形成）或抗凝血剂。