1-(dibromomethyl)cycloheptanol | 1903-16-8

• 分子结构分类: 有机化合物 - 有机卤素化合物
• 英文名称: 1-(dibromomethyl)cycloheptanol
• 英文别名: (bromomethylene)cycloheptane；Brommethylen-cycloheptan；bromomethylidenecycloheptane
• CAS: 1903-16-8
• 化学式: C₈H₁₃Br
• 分子量: 189.095
• InChiKey: KNLLQXWYEHHEPM-UHFFFAOYSA-N

物化性质

• 沸点：
  92 °C(Press: 25 Torr)
• 密度：
  1.369±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2,2'-(3-phenylpropane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 、 1-(dibromomethyl)cycloheptanol 在 C₃₄H₃₈Cl₂F₆FeP₂Pd 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.08h， 以88%的产率得到(S)-2-(1-cycloheptylidene-4-phenylbutan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides

  摘要：

  Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. The so-formed allyl boronates may be oxidized with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonracemic tertiary allylic alcohols. Mechanistic experiments suggest the operation of a pathway involving outer-sphere stereoinvertive transmetalation.

  DOI：

  10.1021/ja510266x
• 作为产物：
  描述：

  bromo-(1-bromo-cycloheptyl)-acetic acid 在 sodium carbonate 作用下， 生成 1-(dibromomethyl)cycloheptanol
  参考文献：
  名称：

  Bromomethylenecycloalkanes

  摘要：

  DOI：

  10.1021/jo01018a021

文献信息

• Pd‐Catalyzed Negishi Cross‐Coupling of Vinyl Bromides with Diborylmethylzinc Chloride
  作者：Minjae Kim、Jun Hee Lee、Seung Hwan Cho

  DOI：10.1002/bkcs.12212

  日期：2021.3

  We have developed Pd‐catalyzed Negishi cross‐coupling of diborylmethylzinc chloride with vinyl bromides. The reaction shows a broad scope and an array of α‐boryl‐substituted allylic boronate esters are obtained in high efficiency.

  我们已经开发了二硼烷基甲基氯化锌与乙烯基溴化物在Pd催化下的Negishi交叉偶联。该反应显示出广阔的范围，并且可以高效地获得一系列α-硼基取代的烯丙基硼酸酯。
• Bromoform Activation. TiCl₄–Mg-Promoted CHBr₂^– and CBr₃^– Transfer to a Variety of Aldehydes and Ketones
  作者：Tu-Hsin Yan、Su-Haur Chang、Cheng-Ta Chang、Chia-Kuan Lin、Chien-Yu Liu

  DOI：10.1021/ol402861a

  日期：2013.11.15

  TiCl4-Mg can mediate addition of CHBr3 to a variety of aldehydes and ketones to form dibromomethyl carbinols and also be used to effect CBr3 transfer to carbonyl groups to form tribromomethyl carbinols. The successful application of TiCl4-Mg-promoted coupling of CHBr3 with various carbonyl compounds, especially in the case of highly enolizable ketones such as 2-indanone and beta-tetralone, highlights the extraordinary reactivity and selectivity and the weakly basic nature of this system.