2-bromo-1-nonen-3-ol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2-bromo-1-nonen-3-ol
• 英文别名: 2-bromonon-1-en-3-ol
• 化学式: C₉H₁₇BrO
• 分子量: 221.137
• InChiKey: YYGJXTYEYYDPJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  正丁基硼酸 、 2-bromo-1-nonen-3-ol 在 dicyclohexyl(2,4,6-trimethoxyphenyl)phosphonium tetrafluoroborate 、 palladium diacetate 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.3h， 以80%的产率得到5-methylene-6-dodecanol
  参考文献：
  名称：

  LB-Phos·HBF4在2-Bromoalken-3-ols与烷基硼酸Suzuki偶联反应中的应用

  摘要：

  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。

  DOI：

  10.1002/ejoc.201200350
• 作为产物：
  描述：

  溴乙烯 、 庚醛 在 正丁基锂 、 lithium bromide 、 三甲基氯硅烷 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 、 various solvents 为溶剂， 反应 0.5h， 以74%的产率得到2-bromo-1-nonen-3-ol
  参考文献：
  名称：

  1-Bromo-1-lithioethene:  A Practical Reagent in Organic Synthesis

  摘要：

  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.

  DOI：

  10.1021/jo051125v

文献信息

• 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。
• 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.
• 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。