2-bromo-4-methylpentanophenone | 33809-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-4-methylpentanophenone
• 英文别名: 2-bromo-4-methyl-1-phenyl-pentan-1-one；2-Brom-4-methyl-1-phenyl-pentan-1-on；α-Brom-isocaprophenon；ω-Brom-ω-isobutyl-acetophenon；2-Bromo-4-methyl-1-phenylpentan-1-one
• CAS: 33809-96-0
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: QYPPBNQXKUFBJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-4-methylpentanophenone 在 sodium tetrahydroborate 、 甲酸 、 硫酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 32.0h， 生成 (2S,3S)-4,5,5-trimethyl-3-(2-methylpropyl)-2-phenylmorpholine
  参考文献：
  名称：

  Boswell, G. Evan; Musso, David L.; Kelley, James L., Journal of Heterocyclic Chemistry, 1996, vol. 33, # 1, p. 33 - 40

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-1-苯基戊烷-1-酮 在 溴 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以30%的产率得到2-bromo-4-methylpentanophenone
  参考文献：
  名称：

  外消旋α-溴酮与芳基锌试剂的催化不对称交叉偶联

  摘要：

  镍盒：已开发出第一种用于将芳基锌试剂与 α-溴酮交叉偶联的催化不对称方法（参见方案）。这种立体会聚的碳-碳键形成过程发生在异常温和的条件下并且没有活化剂，从而允许产生潜在的不稳定的三级立体中心。

  DOI：

  10.1002/anie.200804888

文献信息

• Enantioselective Alkenylation via Nickel-Catalyzed Cross-Coupling with Organozirconium Reagents
  作者：Sha Lou、Gregory C. Fu

  DOI：10.1021/ja1017046

  日期：2010.4.14

  A new family of organometallic compounds, organozirconium reagents, are shown to serve as suitable partners in cross-coupling reactions of (activated) secondary alkyl electrophiles. Thus, the first catalytic method for coupling secondary alpha-bromoketones with alkenylmetal reagents has been developed, specifically, a mild, versatile, and stereoconvergent carbon-carbon bond-forming process that generates

  一个新的有机金属化合物家族，有机锆试剂，被证明可作为（活化的）仲烷基亲电试剂交叉偶联反应的合适伙伴。因此，开发了第一种将仲 α-溴酮与烯基金属试剂偶联的催化方法，特别是一种温和、通用和立体会聚的碳-碳键形成过程，可生成具有良好对映选择性的潜在不稳定 β, γ-不饱和酮。
• Theilig, Chemische Berichte, 1953, vol. 86, p. 96,107
  作者：Theilig

  DOI：——

  日期：——
• Wedekind; Bruch, Justus Liebigs Annalen der Chemie, 1929, vol. 471, p. 98
  作者：Wedekind、Bruch

  DOI：——

  日期：——
• Effects of anti-ecdysteroid azole analogues of metyrapone on the larval development of the fleshfly,<i>Neobellieria bullata</i>
  作者：Iván Bélai、Béla Darvas、Krisztina Bauer、Mahmoud H. Tag El-Din

  DOI：10.1002/ps.2780440304

  日期：1995.7

  AbstractBased on our previous finding that PIM (phenyl‐imidazolyl‐metyra‐pon; 2‐(1‐imidazolyl)‐2‐methyl‐1‐phenylpropan‐1‐one, 1) is a strong inhibitor of ecdysone 20‐monooxygenase (IC50 = 7.89 × 10−7 M) from the fleshfly, Neobellieria bullata (Parker) and has also a good toxic action in vivo against this insect, 17 imidazole and 1,2,4‐triazole analogues of metyrapone were synthesized and evaluated for their action against N. bullata larvae in terms of toxicity, length of larval development, weight of the puparium as well as special symptoms, i.e. malformations of the anterior and posterior spiracles, and of the mandibles. The introduction of p‐methoxy (LC50 = 49 mg kg−1 in diet) or p‐chloro (LC50 = 97 mg kg−1) substituents on the benzene ring of PIM resulted in a significant increase in toxicity compared to that of metyrapone (LC50 = 561 mg kg−1) and PIM (LC50 = 148 mg kg−1). The hybridization state of the carbon atom adjacent to the benzene ring was not an important factor for toxicity because the acetoxy derivative (13) was almost as toxic as PIM. At least one methyl group was required on the carbon atom adjacent to the azole ring to maintain activity, while an ethyl group (4) enhanced the toxic effect. At the applied doses some compounds including metyrapone itself, extended the duration of the larval development. Only metyrapone and PIM decreased the puparium weight. Several derivatives induced lethal malformations of mandibles as well as the anterior and posterior spiracles.
• [EN] PYRAZOL-3-ONES THAT ACTIVATE PRO-APOPTOTIC BAX<br/>[FR] PYRAZOL-3-ONES QUI ACTIVENT LE BAX PRO-APOPTOTIQUE
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2013055949A3

  公开（公告）日：2013-07-04