2-溴-N,N-二丙-2-基-丙酰胺 | 5327-04-8

• 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
• 中文名称: 2-溴-N,N-二丙-2-基-丙酰胺
• 英文名称: N,N-diisopropyl-2-bromopropanamide
• 英文别名: 2-Bromo-n,n-di(propan-2-yl)propanamide
• CAS: 5327-04-8
• 化学式: C₉H₁₈BrNO
• 分子量: 236.152
• InChiKey: FSZNETUUKCPBSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  2-溴-N,N-二丙-2-基-丙酰胺 在 吡啶 、 sodium iodide 、 锌 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 anti-N,N-diisopropyl-3-iodo-2-methylbutanamide
  参考文献：
  名称：

  Diastereodivergency in the reactions of 3-metallated-2-methylbutanamide

  摘要：

  Diastereocontrolled reactions with 3-iodozinc-2-methylbutanamide were examined. When the iodozinc reagent was reacted with aromatic and alpha,beta-unsaturated aldehydes in the presence of iodotrimethylsilane, C2-C3 anti-derivatives were obtained almost exclusively. Whereas, after transmetallation to Ti(IV), the reaction with aldehydes gave C2-C3 syn-derivatives exclusively. Acylation of the zinc reagent with acid chlorides in the presence of Pd(O) catalyst gave C2-C3 syn-derivatives. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10292-7
• 作为产物：
  描述：

  2-溴丙酰溴 、 二异丙胺 以 二氯甲烷 为溶剂， 反应 0.67h， 以20.3 g的产率得到2-溴-N,N-二丙-2-基-丙酰胺
  参考文献：
  名称：

  Diastereodivergency in the reactions of 3-metallated-2-methylbutanamide

  摘要：

  Diastereocontrolled reactions with 3-iodozinc-2-methylbutanamide were examined. When the iodozinc reagent was reacted with aromatic and alpha,beta-unsaturated aldehydes in the presence of iodotrimethylsilane, C2-C3 anti-derivatives were obtained almost exclusively. Whereas, after transmetallation to Ti(IV), the reaction with aldehydes gave C2-C3 syn-derivatives exclusively. Acylation of the zinc reagent with acid chlorides in the presence of Pd(O) catalyst gave C2-C3 syn-derivatives. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10292-7

文献信息

• Organic Dye-Catalyzed Intermolecular Radical Coupling of α-Bromocarbonyls with Olefins: Photocatalytic Synthesis of 1,4-Ketocarbonyls Using Air as an Oxidant
  作者：Soumyadeep Roy Chowdhury、Deepak Singh、Injamam Ul Hoque、Soumitra Maity

  DOI：10.1021/acs.joc.0c01985

  日期：2020.11.6

  α-bromocarbonyls where aerial oxygen played a role of an oxidant to install the keto-oxygen functionality. This unique process is compatible with both internal and terminal olefins and tolerates a diverse array of functional groups (ketone, ester, amide, diketones, ketoester, and malonate). This process is mild and environmentally friendly and deals with greener oxidants like oxygen, affording 1,4-ketocarbonyls as

  在α-溴羰基的帮助下，已经公开了乙烯基芳烃的有机染料催化的可见光促进的酮羰基化方案，其中空气中的氧起氧化剂的作用以安装酮氧官能团。这种独特的方法可与内部和末端烯烃兼容，并能耐受各种官能团（酮，酯，酰胺，二酮，酮酸酯和丙二酸酯）。此过程温和且环保，可处理较绿色的氧化剂，例如氧气，可提供1,4-酮羰基化合物作为增值的最终产品。
• Ni-Catalyzed Mild Arylation of α-Halocarbonyl Compounds with Arylboronic Acids
  作者：Chao Liu、Chuan He、Wei Shi、Mao Chen、Aiwen Lei

  DOI：10.1021/ol702456z

  日期：2007.12.1

  simple yet powerful Ni catalyst can be used to promote direct arylations of alpha-halocarbonyl compounds, including a range of esters, amides, and ketones, with various arylboronic acids under mild conditions. The method tolerates beta-hydrogens and functional groups in the substrates and offers reactivity and selectivity profiles that are complementary to those found in the well-established Buchwald-Hartwig approach.
• Organic Fungicides. II. The Preparation of Some α-Bromopropionamides
  作者：W. E. Weaver、W. M. Whaley

  DOI：10.1021/ja01197a045

  日期：1947.5