(S)-1-bromo-2-(1-methoxyethyl)benzene | 166191-24-8

• 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: (S)-1-bromo-2-(1-methoxyethyl)benzene
• 英文别名: 1-bromo-2-[(1S)-1-methoxyethyl]benzene
• CAS: 166191-24-8
• 化学式: C₉H₁₁BrO
• 分子量: 215.09
• InChiKey: ARONTLUOKIMGCG-ZETCQYMHSA-N

物化性质

• 沸点：
  222.8±15.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-bromo-2-(1-methoxyethyl)benzene 在 正丁基锂 、 碘 作用下， 生成 (S)-1-iodo-2-(1-methoxyethyl)benzene
  参考文献：
  名称：

  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

  摘要：

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

  DOI：

  10.1021/jo980475x
• 作为产物：
  描述：

  2'-溴苯乙酮 在 (S)-BINAP-Ru(II) 氢氧化钾 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 25.0~80.0 ℃ 、8.0 MPa 条件下， 反应 25.0h， 生成 (S)-1-bromo-2-(1-methoxyethyl)benzene
  参考文献：
  名称：

  Phosphane ligands with two binding sites of differing hardness for enantioselective Grignard cross coupling

  摘要：

  一系列新型手性膦被呈现出来，其中每个成员都被设计为在过渡金属介导的不对称Grignard交叉偶联反应中作为配体。这些配体的特点是具有含一个或两个氧原子的侧链，它们具备作为进入的Grignard试剂结合位点的能力。研究中改变了许多化合物的结构参数以深入了解反应机理。多数配体在两种交叉偶联反应中进行了测试，分别用于生成3-苯基丁-1-烯和2,2′-二甲基-1,1′-联萘。虽然这两个系统都获得了适度的对映体过量，但无法对其各自的能力进行比较。

  DOI：

  10.1039/p19960001467

文献信息

• The Mechanism of Double Olefination Using Titanium-Substituted Ylides
  作者：Kelly A. Reynolds、M. G. Finn

  DOI：10.1021/jo9610016

  日期：1997.4.1

  aldehydes is proposed to arise from the presence of a chloride leaving group on the metal. Isolated vinylphosphonium compounds may be deprotonated with phenyllithium to give thermally sensitive allenic phosphoranes, which have been characterized by low temperature multinuclear NMR. The reaction of allenic phosphoranes with aldehydes affords oxaphosphetane and betaine intermediates which appear to interconvert

  从TiCl（3）（OiPr）和（Me（2）N）（3）P = CH（2）衍生的加合物3与NaN（SiMe（3））（2）进行复杂的相互作用醛，导致需要使用过量的两种试剂进行一锅法合成艾伦。当改用TiCl（2）（OiPr）（2）时，与NaN（SiMe（3））（2）的配体取代反应减少，因此可以逐步完成转化，而无需每种试剂过量。有人提出，由金属上存在一个氯化物离去基团来产生由钛取代的基团和醛选择性生产乙烯基phosph盐和副产物氧化钛的方法。分离的乙烯基phosph化合物可以用苯基锂去质子化，得到热敏感的烯丙基磷烷，其特征在于低温多核NMR。烯丙基phosphor烷与醛的反应提供了氧杂磷杂环丁烷和甜菜碱中间体，它们似乎在变暖时会相互转化以产生烯丙基和氧化膦。为了在丙二烯形成过程的两个步骤中高收率都需要二甲氨基取代的磷组分，大概是为了提高受阻的Ti-取代的内酰胺试剂的反应性并稳定烯丙基to烷单元，使其
• Phosphane ligands with two binding sites of differing hardness for enantioselective Grignard cross coupling
  作者：Andreas Terfort、Henri Brunner

  DOI：10.1039/p19960001467

  日期：——

  A series of new, chiral phosphanes is presented, individual members of which were designed to serve as ligands in transition-metal mediated asymmetric Grignard cross coupling reactions. These ligands are characterized by a side chain containing one or two oxygen atoms with the capacity to act as binding sites for the incoming Grignard reagent. A number of structural parameters for the compounds was varied to learn about the reaction mechanism. Most of the ligands were tested in two cross coupling reactions, the formation of 3-phenylbut-1-ene and of 2,2′-dimethyl-1,1′-binaphthyl, respectively. Although both systems gave modest enantiomeric excesses it was not possible to make a comparison of their respective abilities.

  一系列新型手性膦被呈现出来，其中每个成员都被设计为在过渡金属介导的不对称Grignard交叉偶联反应中作为配体。这些配体的特点是具有含一个或两个氧原子的侧链，它们具备作为进入的Grignard试剂结合位点的能力。研究中改变了许多化合物的结构参数以深入了解反应机理。多数配体在两种交叉偶联反应中进行了测试，分别用于生成3-苯基丁-1-烯和2,2′-二甲基-1,1′-联萘。虽然这两个系统都获得了适度的对映体过量，但无法对其各自的能力进行比较。
• Burgess, Kevin; Porte, Alexander M., Angewandte Chemie, 1994, vol. 106, # 11, p. 1218 - 1220
  作者：Burgess, Kevin、Porte, Alexander M.

  DOI：——

  日期：——
• Asymmetric Addition Reactions with Optimized Selenium Electrophiles
  作者：Thomas Wirth、Gianfranco Fragale

  DOI：10.1002/chem.19970031123

  日期：1997.11

  AbstractThe synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.
• Wirth, Thomas, Angewandte Chemie, 1995, vol. 107, # 16, p. 1872 - 1873
  作者：Wirth, Thomas

  DOI：——

  日期：——