2-bromo-1-phenyl-2-propen-1-ol | 96725-18-7

• 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: 2-bromo-1-phenyl-2-propen-1-ol
• 英文别名: 2-bromo-1-phenylprop-2-en-1-ol
• CAS: 96725-18-7
• 化学式: C₉H₉BrO
• 分子量: 213.074
• InChiKey: NAHZCZWMGHZWPD-UHFFFAOYSA-N

物化性质

• 沸点：
  87-88 °C(Press: 0.6 Torr)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-1-phenyl-2-propen-1-ol 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Z-N-benzyl-2-bromo-3-phenyl-2-propenylamine
  参考文献：
  名称：

  β-内酰胺的新合成

  摘要：

  在1-4个CO原子压力下，使用催化量的Pd（OAc）2或PD（acac）2和PPh 3由各种2-溴烯丙胺衍生物2合成α-亚甲基-β-内酰胺3。类似地，由3-烷基-2-溴烯丙基胺19合成α-亚烷基-β-内酰胺20，所述3-烷基-2-溴烯丙基胺以相同的方式容易地由烯烃14制备。

  DOI：

  10.1016/s0040-4020(01)96429-4
• 作为产物：
  描述：

  3-acetoxy-2-bromo-3-phenyl-1-propene 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以95%的产率得到2-bromo-1-phenyl-2-propen-1-ol
  参考文献：
  名称：

  β-内酰胺的新合成

  摘要：

  在1-4个CO原子压力下，使用催化量的Pd（OAc）2或PD（acac）2和PPh 3由各种2-溴烯丙胺衍生物2合成α-亚甲基-β-内酰胺3。类似地，由3-烷基-2-溴烯丙基胺19合成α-亚烷基-β-内酰胺20，所述3-烷基-2-溴烯丙基胺以相同的方式容易地由烯烃14制备。

  DOI：

  10.1016/s0040-4020(01)96429-4

文献信息

• Hydrodebromination of allylic and benzylic bromides with water catalyzed by a rhodium porphyrin complex
  作者：Wu Yang、Chen Chen、Kin Shing Chan

  DOI：10.1039/c8dt02168f

  日期：——

  complex catalyst using water as the hydrogen source without a sacrificial reductant. Mechanistic investigations suggest that bromine atom abstraction via a rhodium porphyrin metalloradical operates to give the rhodium porphyrin alkyl species and the subsequent hydrolysis of the rhodium porphyrin alkyl species to a hydrocarbon product is a key step to harness the hydrogen from water.

  通过使用水作为氢源而没有牺牲还原剂的铑卟啉配合物催化剂成功地实现了烯丙基和苄基溴的加氢脱溴。机理研究表明，通过铑卟啉金属骨架提取溴原子可得到铑卟啉烷基物质，随后铑卟啉烷基物质水解为烃产物是从水中利用氢的关键步骤。
• An Efficient Approach to 2-Bromoalken-3-ols by Regioselective Bromohydroxylation Reaction of Simple Allenes with NBS
  作者：Wangqing Kong、Binjie Guo、Chunling Fu、Shengming Ma

  DOI：10.1002/ejoc.201001676

  日期：2011.4

  A regioselective bromohydroxylation reaction of simple allenes affording 2-bromoalken-3-ols in moderate-to-good yields has been developed by using NBS as the electrophilic reagent in a mixture of 1,4-dioxane/H 2 O (1:1) at room temperature. Through this study it has been concluded that the regioselectivity is determined by various factors including steric and electronic effects of the substituents

  通过在 1,4-二恶烷/H 2 O (1:1) 混合物中使用 NBS 作为亲电试剂，开发了简单丙二烯的区域选择性溴羟基化反应，以中等至良好的收率提供 2-bromoalken-3-ols在室温下。通过这项研究得出的结论是，区域选择性由各种因素决定，包括丙二烯部分取代基的空间和电子效应。
• Application of LB-Phos·HBF4 in the Suzuki Coupling Reaction of 2-Bromoalken-3-ols with Alkylboronic Acids
  作者：Binjie Guo、Chunling Fu、Shengming Ma

  DOI：10.1002/ejoc.201200350

  日期：2012.7

  LB-Phos·HBF4 was used in the Suzuki coupling reaction of 2-bromoalken-3-ols with alkylboronic acids to give the coupling products in moderate to good yields. Substituents such as benzyl, phenyl, allyl, and alkyl are tolerated at the 1- and 3-positions of the 2-bromoalken-3-ols. The reactions of both primary and secondary alkylboronic acids proceed smoothly.

  LB-Phos·HBF4用于2-bromoalken-3-ols与烷基硼酸的Suzuki偶联反应，以中等至良好的产率得到偶联产物。取代基如苄基、苯基、烯丙基和烷基在 2-溴链烯-3-醇的 1-和 3-位是可耐受的。伯烷基硼酸和仲烷基硼酸的反应均顺利进行。
• 1-Bromo-1-lithioethene:  A Practical Reagent for the Efficient Preparation of 2-Bromo-1-alken-3-ols
  作者：Yehor Y. Novikov、Paul Sampson

  DOI：10.1021/ol034594x

  日期：2003.6.1

  A reliable preparative-scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -105 degreesC to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Efficient diastereoselective addition to alpha-siloxy and alpha-methylcyclohexanones, as well as protected 3-keto furanose sugars, is achieved in the presence of 10 mol % CeBr3. The resulting bromoallylic alcohol adducts have considerable potential as synthetic building blocks.
• 1-Bromo-1-lithioethene:  A Practical Reagent in Organic Synthesis
  作者：Yehor Y. Novikov、Paul Sampson

  DOI：10.1021/jo051125v

  日期：2005.12.1

  A reliable preparative scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -110 degrees C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Trapping with other electrophiles (acylsilanes, chlorosilanes, tributyltin chloride, iodine) cleanly provides practically useful yields of various 1-substituted 1-bromoethene products. Unexpectedly high diastereoselectivities were observed during the addition of 1-bromo-1-lithioethene to alpha-siloxy aldehydes (typically 10:1, Felkin-Ahn control) and protected ketopyranose and ketofuranose sugars (>= 10:1, addition from the less-hindered face). The title organolithium reagent possesses relatively low basicity at low temperature, and is compatible with a variety of common protecting groups. We believe that these unusual properties of 1-bronio-1-lithioethene may originate from the specific crystalline structure of the reagent in which lithium is coordinatively saturated and thus unavailable for chelation.